Studies of non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: Synthesis and structure-activity relationships of 2-cyano and 2-hydroxy thiazolidenebenzenesulfonamide derivatives
Identifieur interne : 000565 ( PascalFrancis/Checkpoint ); précédent : 000564; suivant : 000566Studies of non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: Synthesis and structure-activity relationships of 2-cyano and 2-hydroxy thiazolidenebenzenesulfonamide derivatives
Auteurs : Naoyuki Masuda [Japon] ; Osamu Yamamoto [Japon] ; Masahiro Fujii [Japon] ; Tetsuro Ohgami [Japon] ; Jiro Fujiyasu [Japon] ; Toru Kontani [Japon] ; Ayako Moritomo [Japon] ; Masaya Orita [Japon] ; Hiroyuki Kurihara [Japon] ; Hironobu Koga [Japon] ; Shunji Kageyama [Japon] ; Mitsuaki Ohta [Japon] ; Hiroshi Inoue [Japon] ; Toshifumi Hatta [Japon] ; Masafumi Shintani [Japon] ; Hiroshi Suzuki [Japon] ; Kenji Sudo [Japon] ; Yasuaki Shimizu [Japon] ; Eiichi Kodama [Japon] ; Masao Matsuoka [Japon] ; Masatoshi Fujiwara [Japon] ; Tomoyuki Yokota [Japon] ; Shiro Shigeta [Japon] ; Masanori Baba [Japon]Source :
- Bioorganic & medicinal chemistry [ 0968-0896 ] ; 2005.
Descripteurs français
- Pascal (Inist)
- Relation structure activité, Synthèse chimique, Sulfonamide, Thiazole dérivé, Nitrile, Benzène dérivé, Hétérocycle soufre azote, Composé non nucléoside, Inhibiteur enzyme, Inhibiteur reverse transcriptase, RNA-directed DNA polymerase, Antiviral, Virus HIV1, In vitro, Anti hiv, Benzènesulfonamide(5-chloro-2-cyano-N-[3,4-diméthyl-5-isopropylthiazolin-2-ylidène]), Benzènesulfonamide(5-bromo-N-[4-chloro-5-isopropyl-3-méthylthiazolin-2-ylidène]-2-hydroxy), Benzène-1,4-dicarbonitrile dérivé, Benzènesulfonamide(2,5-dicyano-N-[3,4-diméthyl-5-isopropylthiazolin-2-ylidène]), YM 215389, YM 228855.
English descriptors
- KwdEn :
Abstract
In a previous study, we described the structure-activity relationships (SARs) for a series of thiazolidenebenzenesulfonamide derivatives. These compounds were found to be highly potent inhibitors of the wild type (WT) and Y181C mutant reverse transcriptases (RTs) and modest inhibitors of K103N RT. These molecules are thus considered to be a novel class of non-nucleoside HIV-1 RT inhibitors (NNRTIs). In this paper, we have examined the effects of substituents on both the thiazolidene and benzenesulfonamide moieties. Introduction of a 2-cyanophenyl ring into these moieties significantly enhanced anti-HIV-1 activity, whereas a 2-hydroxyphenyl group endowed potent activity against RTs, including K103N and Y181C mutants. Among the series of molecules examined, 101 and 18b (YM-228855), combinations of 2-cyanophenyl and 4-methyl-5-isopropylthiazole moieties, showed extremely potent anti-HIV-1 activity. The EC50 values of 101 and 18b were 0.0017 and 0.0018 μM, respectively. These values were lower than that of efavirenz (3). Compound 11g (YM-215389), a combination of 2-hydroxyphenyl and 4-chloro-5-isopropylthiazole moieties, proved to be the most active against both K103N and Y181C RTs with IC50 values of 0.043 and 0.013 μM, respectively.
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Yamamoto</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Fujii, Masahiro" sort="Fujii, Masahiro" uniqKey="Fujii M" first="Masahiro" last="Fujii">Masahiro Fujii</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 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Inoue</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Hatta, Toshifumi" sort="Hatta, Toshifumi" uniqKey="Hatta T" first="Toshifumi" last="Hatta">Toshifumi Hatta</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Shintani, Masafumi" sort="Shintani, Masafumi" uniqKey="Shintani M" first="Masafumi" last="Shintani">Masafumi Shintani</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Suzuki, Hiroshi" sort="Suzuki, Hiroshi" uniqKey="Suzuki H" first="Hiroshi" last="Suzuki">Hiroshi Suzuki</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Sudo, Kenji" sort="Sudo, Kenji" uniqKey="Sudo K" first="Kenji" last="Sudo">Kenji Sudo</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Shimizu, Yasuaki" sort="Shimizu, Yasuaki" uniqKey="Shimizu Y" first="Yasuaki" last="Shimizu">Yasuaki Shimizu</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Kodama, Eiichi" sort="Kodama, Eiichi" uniqKey="Kodama E" first="Eiichi" last="Kodama">Eiichi Kodama</name><affiliation wicri:level="4"><inist:fA14 i1="02"><s1>Laboratory of Virus Immunology, Institute for Virus Research, Kyoto University, 53 Syogoin, Kawaramachi</s1><s2>Sakyo-ku, Kyoto 606-8507</s2><s3>JPN</s3><sZ>19 aut.</sZ><sZ>20 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Sakyo-ku, Kyoto 606-8507</wicri:noRegion><orgName type="university">Université de Kyoto</orgName><placeName><settlement type="city">Kyoto</settlement><region type="prefecture">Région du Kansai</region></placeName></affiliation></author><author><name sortKey="Matsuoka, Masao" sort="Matsuoka, Masao" uniqKey="Matsuoka M" first="Masao" last="Matsuoka">Masao Matsuoka</name><affiliation wicri:level="4"><inist:fA14 i1="02"><s1>Laboratory of Virus Immunology, Institute for Virus Research, Kyoto University, 53 Syogoin, Kawaramachi</s1><s2>Sakyo-ku, Kyoto 606-8507</s2><s3>JPN</s3><sZ>19 aut.</sZ><sZ>20 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Sakyo-ku, Kyoto 606-8507</wicri:noRegion><orgName type="university">Université de Kyoto</orgName><placeName><settlement type="city">Kyoto</settlement><region type="prefecture">Région du Kansai</region></placeName></affiliation></author><author><name sortKey="Fujiwara, Masatoshi" sort="Fujiwara, Masatoshi" uniqKey="Fujiwara M" first="Masatoshi" last="Fujiwara">Masatoshi Fujiwara</name><affiliation wicri:level="1"><inist:fA14 i1="03"><s1>Rational Drug Design Laboratories, 4-1-1, Misato</s1><s2>Matsukawa-Machi, Fukushima 960-1242</s2><s3>JPN</s3><sZ>21 aut.</sZ><sZ>22 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Matsukawa-Machi, Fukushima 960-1242</wicri:noRegion></affiliation></author><author><name sortKey="Yokota, Tomoyuki" sort="Yokota, Tomoyuki" uniqKey="Yokota T" first="Tomoyuki" last="Yokota">Tomoyuki Yokota</name><affiliation wicri:level="1"><inist:fA14 i1="03"><s1>Rational Drug Design Laboratories, 4-1-1, Misato</s1><s2>Matsukawa-Machi, Fukushima 960-1242</s2><s3>JPN</s3><sZ>21 aut.</sZ><sZ>22 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Matsukawa-Machi, Fukushima 960-1242</wicri:noRegion></affiliation></author><author><name sortKey="Shigeta, Shiro" sort="Shigeta, Shiro" uniqKey="Shigeta S" first="Shiro" last="Shigeta">Shiro Shigeta</name><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>Department of Microbiology, School of Medicine, Fukushima Medical University</s1><s2>I Hikarigaoka, Fukushima 960-1295</s2><s3>JPN</s3><sZ>23 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>I Hikarigaoka, Fukushima 960-1295</wicri:noRegion></affiliation></author><author><name sortKey="Baba, Masanori" sort="Baba, Masanori" uniqKey="Baba M" first="Masanori" last="Baba">Masanori Baba</name><affiliation wicri:level="1"><inist:fA14 i1="05"><s1>Division of Antiviral Chemotherapy, Center for Chronic Viral Diseases, Graduate School of Medical and Dental Sciences, Kagoshima University</s1><s2>8-35-1 Sakuragaoka, Kagoshima 890-8544</s2><s3>JPN</s3><sZ>24 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>8-35-1 Sakuragaoka, Kagoshima 890-8544</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">INIST</idno><idno type="inist">05-0202368</idno><date when="2005">2005</date><idno type="stanalyst">PASCAL 05-0202368 INIST</idno><idno type="RBID">Pascal:05-0202368</idno><idno type="wicri:Area/PascalFrancis/Corpus">000701</idno><idno type="wicri:Area/PascalFrancis/Curation">000289</idno><idno type="wicri:Area/PascalFrancis/Checkpoint">000565</idno><idno type="wicri:explorRef" wicri:stream="PascalFrancis" wicri:step="Checkpoint">000565</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a">Studies of non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: Synthesis and structure-activity relationships of 2-cyano and 2-hydroxy thiazolidenebenzenesulfonamide derivatives</title><author><name sortKey="Masuda, Naoyuki" sort="Masuda, Naoyuki" uniqKey="Masuda N" first="Naoyuki" last="Masuda">Naoyuki Masuda</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Yamamoto, Osamu" sort="Yamamoto, Osamu" uniqKey="Yamamoto O" first="Osamu" last="Yamamoto">Osamu Yamamoto</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Fujii, Masahiro" sort="Fujii, Masahiro" uniqKey="Fujii M" first="Masahiro" last="Fujii">Masahiro Fujii</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Ohgami, Tetsuro" sort="Ohgami, Tetsuro" uniqKey="Ohgami T" first="Tetsuro" last="Ohgami">Tetsuro Ohgami</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Fujiyasu, Jiro" sort="Fujiyasu, Jiro" uniqKey="Fujiyasu J" first="Jiro" last="Fujiyasu">Jiro Fujiyasu</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Kontani, Toru" sort="Kontani, Toru" uniqKey="Kontani T" first="Toru" last="Kontani">Toru Kontani</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Moritomo, Ayako" sort="Moritomo, Ayako" uniqKey="Moritomo A" first="Ayako" last="Moritomo">Ayako Moritomo</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Orita, Masaya" sort="Orita, Masaya" uniqKey="Orita M" first="Masaya" last="Orita">Masaya Orita</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Kurihara, Hiroyuki" sort="Kurihara, Hiroyuki" uniqKey="Kurihara H" first="Hiroyuki" last="Kurihara">Hiroyuki Kurihara</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Koga, Hironobu" sort="Koga, Hironobu" uniqKey="Koga H" first="Hironobu" last="Koga">Hironobu Koga</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Kageyama, Shunji" sort="Kageyama, Shunji" uniqKey="Kageyama S" first="Shunji" last="Kageyama">Shunji Kageyama</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Ohta, Mitsuaki" sort="Ohta, Mitsuaki" uniqKey="Ohta M" first="Mitsuaki" last="Ohta">Mitsuaki Ohta</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Inoue, Hiroshi" sort="Inoue, Hiroshi" uniqKey="Inoue H" first="Hiroshi" last="Inoue">Hiroshi Inoue</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Hatta, Toshifumi" sort="Hatta, Toshifumi" uniqKey="Hatta T" first="Toshifumi" last="Hatta">Toshifumi Hatta</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Shintani, Masafumi" sort="Shintani, Masafumi" uniqKey="Shintani M" first="Masafumi" last="Shintani">Masafumi Shintani</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Suzuki, Hiroshi" sort="Suzuki, Hiroshi" uniqKey="Suzuki H" first="Hiroshi" last="Suzuki">Hiroshi Suzuki</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Sudo, Kenji" sort="Sudo, Kenji" uniqKey="Sudo K" first="Kenji" last="Sudo">Kenji Sudo</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Shimizu, Yasuaki" sort="Shimizu, Yasuaki" uniqKey="Shimizu Y" first="Yasuaki" last="Shimizu">Yasuaki Shimizu</name><affiliation wicri:level="1"><inist:fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Tsukuba, Ibaraki 305-8585</wicri:noRegion></affiliation></author><author><name sortKey="Kodama, Eiichi" sort="Kodama, Eiichi" uniqKey="Kodama E" first="Eiichi" last="Kodama">Eiichi Kodama</name><affiliation wicri:level="4"><inist:fA14 i1="02"><s1>Laboratory of Virus Immunology, Institute for Virus Research, Kyoto University, 53 Syogoin, Kawaramachi</s1><s2>Sakyo-ku, Kyoto 606-8507</s2><s3>JPN</s3><sZ>19 aut.</sZ><sZ>20 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Sakyo-ku, Kyoto 606-8507</wicri:noRegion><orgName type="university">Université de Kyoto</orgName><placeName><settlement type="city">Kyoto</settlement><region type="prefecture">Région du Kansai</region></placeName></affiliation></author><author><name sortKey="Matsuoka, Masao" sort="Matsuoka, Masao" uniqKey="Matsuoka M" first="Masao" last="Matsuoka">Masao Matsuoka</name><affiliation wicri:level="4"><inist:fA14 i1="02"><s1>Laboratory of Virus Immunology, Institute for Virus Research, Kyoto University, 53 Syogoin, Kawaramachi</s1><s2>Sakyo-ku, Kyoto 606-8507</s2><s3>JPN</s3><sZ>19 aut.</sZ><sZ>20 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Sakyo-ku, Kyoto 606-8507</wicri:noRegion><orgName type="university">Université de Kyoto</orgName><placeName><settlement type="city">Kyoto</settlement><region type="prefecture">Région du Kansai</region></placeName></affiliation></author><author><name sortKey="Fujiwara, Masatoshi" sort="Fujiwara, Masatoshi" uniqKey="Fujiwara M" first="Masatoshi" last="Fujiwara">Masatoshi Fujiwara</name><affiliation wicri:level="1"><inist:fA14 i1="03"><s1>Rational Drug Design Laboratories, 4-1-1, Misato</s1><s2>Matsukawa-Machi, Fukushima 960-1242</s2><s3>JPN</s3><sZ>21 aut.</sZ><sZ>22 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Matsukawa-Machi, Fukushima 960-1242</wicri:noRegion></affiliation></author><author><name sortKey="Yokota, Tomoyuki" sort="Yokota, Tomoyuki" uniqKey="Yokota T" first="Tomoyuki" last="Yokota">Tomoyuki Yokota</name><affiliation wicri:level="1"><inist:fA14 i1="03"><s1>Rational Drug Design Laboratories, 4-1-1, Misato</s1><s2>Matsukawa-Machi, Fukushima 960-1242</s2><s3>JPN</s3><sZ>21 aut.</sZ><sZ>22 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>Matsukawa-Machi, Fukushima 960-1242</wicri:noRegion></affiliation></author><author><name sortKey="Shigeta, Shiro" sort="Shigeta, Shiro" uniqKey="Shigeta S" first="Shiro" last="Shigeta">Shiro Shigeta</name><affiliation wicri:level="1"><inist:fA14 i1="04"><s1>Department of Microbiology, School of Medicine, Fukushima Medical University</s1><s2>I Hikarigaoka, Fukushima 960-1295</s2><s3>JPN</s3><sZ>23 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>I Hikarigaoka, Fukushima 960-1295</wicri:noRegion></affiliation></author><author><name sortKey="Baba, Masanori" sort="Baba, Masanori" uniqKey="Baba M" first="Masanori" last="Baba">Masanori Baba</name><affiliation wicri:level="1"><inist:fA14 i1="05"><s1>Division of Antiviral Chemotherapy, Center for Chronic Viral Diseases, Graduate School of Medical and Dental Sciences, Kagoshima University</s1><s2>8-35-1 Sakuragaoka, Kagoshima 890-8544</s2><s3>JPN</s3><sZ>24 aut.</sZ></inist:fA14><country>Japon</country><wicri:noRegion>8-35-1 Sakuragaoka, Kagoshima 890-8544</wicri:noRegion></affiliation></author></analytic><series><title level="j" type="main">Bioorganic & medicinal chemistry</title><title level="j" type="abbreviated">Bioorg. med. chem.</title><idno type="ISSN">0968-0896</idno><imprint><date when="2005">2005</date></imprint></series></biblStruct></sourceDesc><seriesStmt><title level="j" type="main">Bioorganic & medicinal chemistry</title><title level="j" type="abbreviated">Bioorg. med. chem.</title><idno type="ISSN">0968-0896</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral</term><term>Benzene derivatives</term><term>Chemical synthesis</term><term>Enzyme inhibitor</term><term>HIV-1 virus</term><term>In vitro</term><term>Nitrile</term><term>Non nucleoside compound</term><term>RNA-directed DNA polymerase</term><term>Reverse transcriptase inhibitor</term><term>Structure activity relation</term><term>Sulfonamide</term><term>Sulfur nitrogen heterocycle</term><term>Thiazole derivatives</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Relation structure activité</term><term>Synthèse chimique</term><term>Sulfonamide</term><term>Thiazole dérivé</term><term>Nitrile</term><term>Benzène dérivé</term><term>Hétérocycle soufre azote</term><term>Composé non nucléoside</term><term>Inhibiteur enzyme</term><term>Inhibiteur reverse transcriptase</term><term>RNA-directed DNA polymerase</term><term>Antiviral</term><term>Virus HIV1</term><term>In vitro</term><term>Anti hiv</term><term>Benzènesulfonamide(5-chloro-2-cyano-N-[3,4-diméthyl-5-isopropylthiazolin-2-ylidène])</term><term>Benzènesulfonamide(5-bromo-N-[4-chloro-5-isopropyl-3-méthylthiazolin-2-ylidène]-2-hydroxy)</term><term>Benzène-1,4-dicarbonitrile dérivé</term><term>Benzènesulfonamide(2,5-dicyano-N-[3,4-diméthyl-5-isopropylthiazolin-2-ylidène])</term><term>YM 215389</term><term>YM 228855</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">In a previous study, we described the structure-activity relationships (SARs) for a series of thiazolidenebenzenesulfonamide derivatives. These compounds were found to be highly potent inhibitors of the wild type (WT) and Y181C mutant reverse transcriptases (RTs) and modest inhibitors of K103N RT. These molecules are thus considered to be a novel class of non-nucleoside HIV-1 RT inhibitors (NNRTIs). In this paper, we have examined the effects of substituents on both the thiazolidene and benzenesulfonamide moieties. Introduction of a 2-cyanophenyl ring into these moieties significantly enhanced anti-HIV-1 activity, whereas a 2-hydroxyphenyl group endowed potent activity against RTs, including K103N and Y181C mutants. Among the series of molecules examined, 101 and 18b (YM-228855), combinations of 2-cyanophenyl and 4-methyl-5-isopropylthiazole moieties, showed extremely potent anti-HIV-1 activity. The EC<sub>50</sub> values of 101 and 18b were 0.0017 and 0.0018 μM, respectively. These values were lower than that of efavirenz (3). Compound 11g (YM-215389), a combination of 2-hydroxyphenyl and 4-chloro-5-isopropylthiazole moieties, proved to be the most active against both K103N and Y181C RTs with IC<sub>50</sub> values of 0.043 and 0.013 μM, respectively.</div></front></TEI><inist><standard h6="B"><pA><fA01 i1="01" i2="1"><s0>0968-0896</s0></fA01><fA03 i2="1"><s0>Bioorg. med. chem.</s0></fA03><fA05><s2>13</s2></fA05><fA06><s2>4</s2></fA06><fA08 i1="01" i2="1" l="ENG"><s1>Studies of non-nucleoside HIV-1 reverse transcriptase inhibitors. Part 2: Synthesis and structure-activity relationships of 2-cyano and 2-hydroxy thiazolidenebenzenesulfonamide derivatives</s1></fA08><fA11 i1="01" i2="1"><s1>MASUDA (Naoyuki)</s1></fA11><fA11 i1="02" i2="1"><s1>YAMAMOTO (Osamu)</s1></fA11><fA11 i1="03" i2="1"><s1>FUJII (Masahiro)</s1></fA11><fA11 i1="04" i2="1"><s1>OHGAMI (Tetsuro)</s1></fA11><fA11 i1="05" i2="1"><s1>FUJIYASU (Jiro)</s1></fA11><fA11 i1="06" i2="1"><s1>KONTANI (Toru)</s1></fA11><fA11 i1="07" i2="1"><s1>MORITOMO (Ayako)</s1></fA11><fA11 i1="08" i2="1"><s1>ORITA (Masaya)</s1></fA11><fA11 i1="09" i2="1"><s1>KURIHARA (Hiroyuki)</s1></fA11><fA11 i1="10" i2="1"><s1>KOGA (Hironobu)</s1></fA11><fA11 i1="11" i2="1"><s1>KAGEYAMA (Shunji)</s1></fA11><fA11 i1="12" i2="1"><s1>OHTA (Mitsuaki)</s1></fA11><fA11 i1="13" i2="1"><s1>INOUE (Hiroshi)</s1></fA11><fA11 i1="14" i2="1"><s1>HATTA (Toshifumi)</s1></fA11><fA11 i1="15" i2="1"><s1>SHINTANI (Masafumi)</s1></fA11><fA11 i1="16" i2="1"><s1>SUZUKI (Hiroshi)</s1></fA11><fA11 i1="17" i2="1"><s1>SUDO (Kenji)</s1></fA11><fA11 i1="18" i2="1"><s1>SHIMIZU (Yasuaki)</s1></fA11><fA11 i1="19" i2="1"><s1>KODAMA (Eiichi)</s1></fA11><fA11 i1="20" i2="1"><s1>MATSUOKA (Masao)</s1></fA11><fA11 i1="21" i2="1"><s1>FUJIWARA (Masatoshi)</s1></fA11><fA11 i1="22" i2="1"><s1>YOKOTA (Tomoyuki)</s1></fA11><fA11 i1="23" i2="1"><s1>SHIGETA (Shiro)</s1></fA11><fA11 i1="24" i2="1"><s1>BABA (Masanori)</s1></fA11><fA14 i1="01"><s1>Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd., 21 Miyukigaoka</s1><s2>Tsukuba, Ibaraki 305-8585</s2><s3>JPN</s3><sZ>1 aut.</sZ><sZ>2 aut.</sZ><sZ>3 aut.</sZ><sZ>4 aut.</sZ><sZ>5 aut.</sZ><sZ>6 aut.</sZ><sZ>7 aut.</sZ><sZ>8 aut.</sZ><sZ>9 aut.</sZ><sZ>10 aut.</sZ><sZ>11 aut.</sZ><sZ>12 aut.</sZ><sZ>13 aut.</sZ><sZ>14 aut.</sZ><sZ>15 aut.</sZ><sZ>16 aut.</sZ><sZ>17 aut.</sZ><sZ>18 aut.</sZ></fA14><fA14 i1="02"><s1>Laboratory of Virus Immunology, Institute for Virus Research, Kyoto University, 53 Syogoin, Kawaramachi</s1><s2>Sakyo-ku, Kyoto 606-8507</s2><s3>JPN</s3><sZ>19 aut.</sZ><sZ>20 aut.</sZ></fA14><fA14 i1="03"><s1>Rational Drug Design Laboratories, 4-1-1, Misato</s1><s2>Matsukawa-Machi, Fukushima 960-1242</s2><s3>JPN</s3><sZ>21 aut.</sZ><sZ>22 aut.</sZ></fA14><fA14 i1="04"><s1>Department of Microbiology, School of Medicine, Fukushima Medical University</s1><s2>I Hikarigaoka, Fukushima 960-1295</s2><s3>JPN</s3><sZ>23 aut.</sZ></fA14><fA14 i1="05"><s1>Division of Antiviral Chemotherapy, Center for Chronic Viral Diseases, Graduate School of Medical and Dental Sciences, Kagoshima University</s1><s2>8-35-1 Sakuragaoka, Kagoshima 890-8544</s2><s3>JPN</s3><sZ>24 aut.</sZ></fA14><fA20><s1>949-961</s1></fA20><fA21><s1>2005</s1></fA21><fA23 i1="01"><s0>ENG</s0></fA23><fA43 i1="01"><s1>INIST</s1><s2>26564</s2><s5>354000125945790020</s5></fA43><fA44><s0>0000</s0><s1>© 2005 INIST-CNRS. All rights reserved.</s1></fA44><fA45><s0>15 ref.</s0></fA45><fA47 i1="01" i2="1"><s0>05-0202368</s0></fA47><fA60><s1>P</s1></fA60><fA61><s0>A</s0></fA61><fA64 i1="01" i2="1"><s0>Bioorganic & medicinal chemistry</s0></fA64><fA66 i1="01"><s0>GBR</s0></fA66><fC01 i1="01" l="ENG"><s0>In a previous study, we described the structure-activity relationships (SARs) for a series of thiazolidenebenzenesulfonamide derivatives. These compounds were found to be highly potent inhibitors of the wild type (WT) and Y181C mutant reverse transcriptases (RTs) and modest inhibitors of K103N RT. These molecules are thus considered to be a novel class of non-nucleoside HIV-1 RT inhibitors (NNRTIs). In this paper, we have examined the effects of substituents on both the thiazolidene and benzenesulfonamide moieties. Introduction of a 2-cyanophenyl ring into these moieties significantly enhanced anti-HIV-1 activity, whereas a 2-hydroxyphenyl group endowed potent activity against RTs, including K103N and Y181C mutants. Among the series of molecules examined, 101 and 18b (YM-228855), combinations of 2-cyanophenyl and 4-methyl-5-isopropylthiazole moieties, showed extremely potent anti-HIV-1 activity. The EC<sub>50</sub> values of 101 and 18b were 0.0017 and 0.0018 μM, respectively. These values were lower than that of efavirenz (3). Compound 11g (YM-215389), a combination of 2-hydroxyphenyl and 4-chloro-5-isopropylthiazole moieties, proved to be the most active against both K103N and Y181C RTs with IC<sub>50</sub> values of 0.043 and 0.013 μM, respectively.</s0></fC01><fC02 i1="01" i2="X"><s0>002B02S05</s0></fC02><fC03 i1="01" i2="X" l="FRE"><s0>Relation structure activité</s0><s5>01</s5></fC03><fC03 i1="01" i2="X" l="ENG"><s0>Structure activity relation</s0><s5>01</s5></fC03><fC03 i1="01" i2="X" l="SPA"><s0>Relación estructura actividad</s0><s5>01</s5></fC03><fC03 i1="02" i2="X" l="FRE"><s0>Synthèse chimique</s0><s5>02</s5></fC03><fC03 i1="02" i2="X" l="ENG"><s0>Chemical synthesis</s0><s5>02</s5></fC03><fC03 i1="02" i2="X" l="SPA"><s0>Síntesis química</s0><s5>02</s5></fC03><fC03 i1="03" i2="X" l="FRE"><s0>Sulfonamide</s0><s5>03</s5></fC03><fC03 i1="03" i2="X" l="ENG"><s0>Sulfonamide</s0><s5>03</s5></fC03><fC03 i1="03" i2="X" l="SPA"><s0>Sulfonamida</s0><s5>03</s5></fC03><fC03 i1="04" i2="X" l="FRE"><s0>Thiazole dérivé</s0><s5>04</s5></fC03><fC03 i1="04" i2="X" l="ENG"><s0>Thiazole derivatives</s0><s5>04</s5></fC03><fC03 i1="04" i2="X" l="SPA"><s0>Tiazol derivado</s0><s5>04</s5></fC03><fC03 i1="05" i2="X" l="FRE"><s0>Nitrile</s0><s5>05</s5></fC03><fC03 i1="05" i2="X" l="ENG"><s0>Nitrile</s0><s5>05</s5></fC03><fC03 i1="05" i2="X" l="SPA"><s0>Nitrilo</s0><s5>05</s5></fC03><fC03 i1="06" i2="X" l="FRE"><s0>Benzène dérivé</s0><s5>06</s5></fC03><fC03 i1="06" i2="X" l="ENG"><s0>Benzene derivatives</s0><s5>06</s5></fC03><fC03 i1="06" i2="X" l="SPA"><s0>Benceno derivado</s0><s5>06</s5></fC03><fC03 i1="07" i2="X" l="FRE"><s0>Hétérocycle soufre azote</s0><s5>09</s5></fC03><fC03 i1="07" i2="X" l="ENG"><s0>Sulfur nitrogen heterocycle</s0><s5>09</s5></fC03><fC03 i1="07" i2="X" l="SPA"><s0>Heterociclo azufre nitrógeno</s0><s5>09</s5></fC03><fC03 i1="08" i2="X" l="FRE"><s0>Composé non nucléoside</s0><s5>10</s5></fC03><fC03 i1="08" i2="X" l="ENG"><s0>Non nucleoside compound</s0><s5>10</s5></fC03><fC03 i1="08" 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l="ENG"><s0>Antiviral</s0><s5>19</s5></fC03><fC03 i1="12" i2="X" l="SPA"><s0>Antiviral</s0><s5>19</s5></fC03><fC03 i1="13" i2="X" l="FRE"><s0>Virus HIV1</s0><s2>NW</s2><s5>20</s5></fC03><fC03 i1="13" i2="X" l="ENG"><s0>HIV-1 virus</s0><s2>NW</s2><s5>20</s5></fC03><fC03 i1="13" i2="X" l="SPA"><s0>HIV-1 virus</s0><s2>NW</s2><s5>20</s5></fC03><fC03 i1="14" i2="X" l="FRE"><s0>In vitro</s0><s5>21</s5></fC03><fC03 i1="14" i2="X" l="ENG"><s0>In vitro</s0><s5>21</s5></fC03><fC03 i1="14" i2="X" l="SPA"><s0>In vitro</s0><s5>21</s5></fC03><fC03 i1="15" i2="X" l="FRE"><s0>Anti hiv</s0><s4>INC</s4><s5>77</s5></fC03><fC03 i1="16" i2="X" l="FRE"><s0>Benzènesulfonamide(5-chloro-2-cyano-N-[3,4-diméthyl-5-isopropylthiazolin-2-ylidène])</s0><s2>FR</s2><s2>NK</s2><s4>INC</s4><s5>78</s5></fC03><fC03 i1="17" i2="X" l="FRE"><s0>Benzènesulfonamide(5-bromo-N-[4-chloro-5-isopropyl-3-méthylthiazolin-2-ylidène]-2-hydroxy)</s0><s2>FR</s2><s2>NK</s2><s4>INC</s4><s5>79</s5></fC03><fC03 i1="18" i2="X" l="FRE"><s0>Benzène-1,4-dicarbonitrile dérivé</s0><s2>NK</s2><s4>INC</s4><s5>80</s5></fC03><fC03 i1="19" i2="X" l="FRE"><s0>Benzènesulfonamide(2,5-dicyano-N-[3,4-diméthyl-5-isopropylthiazolin-2-ylidène])</s0><s2>FR</s2><s2>NK</s2><s4>INC</s4><s5>81</s5></fC03><fC03 i1="20" i2="X" l="FRE"><s0>YM 215389</s0><s2>FR</s2><s4>INC</s4><s5>82</s5></fC03><fC03 i1="21" i2="X" l="FRE"><s0>YM 228855</s0><s2>FR</s2><s4>INC</s4><s5>83</s5></fC03><fC07 i1="01" i2="X" l="FRE"><s0>Chlore Composé organique</s0><s2>NC</s2><s2>FX</s2><s2>NA</s2><s5>07</s5></fC07><fC07 i1="01" i2="X" l="ENG"><s0>Chlorine Organic compounds</s0><s2>NC</s2><s2>FX</s2><s2>NA</s2><s5>07</s5></fC07><fC07 i1="01" i2="X" l="SPA"><s0>Cloro Compuesto orgánico</s0><s2>NC</s2><s2>FX</s2><s2>NA</s2><s5>07</s5></fC07><fC07 i1="02" i2="X" l="FRE"><s0>Brome Composé organique</s0><s2>NC</s2><s2>FR</s2><s2>FX</s2><s2>NA</s2><s5>08</s5></fC07><fC07 i1="02" i2="X" l="ENG"><s0>Bromine Organic compounds</s0><s2>NC</s2><s2>FR</s2><s2>FX</s2><s2>NA</s2><s5>08</s5></fC07><fC07 i1="02" i2="X" l="SPA"><s0>Bromo Compuesto orgánico</s0><s2>NC</s2><s2>FR</s2><s2>FX</s2><s2>NA</s2><s5>08</s5></fC07><fC07 i1="03" i2="X" l="FRE"><s0>Nucleotidyltransferases</s0><s2>FE</s2></fC07><fC07 i1="03" i2="X" l="ENG"><s0>Nucleotidyltransferases</s0><s2>FE</s2></fC07><fC07 i1="03" i2="X" l="SPA"><s0>Nucleotidyltransferases</s0><s2>FE</s2></fC07><fC07 i1="04" i2="X" l="FRE"><s0>Transferases</s0><s2>FE</s2></fC07><fC07 i1="04" i2="X" l="ENG"><s0>Transferases</s0><s2>FE</s2></fC07><fC07 i1="04" i2="X" l="SPA"><s0>Transferases</s0><s2>FE</s2></fC07><fC07 i1="05" i2="X" l="FRE"><s0>Enzyme</s0><s2>FE</s2></fC07><fC07 i1="05" i2="X" l="ENG"><s0>Enzyme</s0><s2>FE</s2></fC07><fC07 i1="05" i2="X" l="SPA"><s0>Enzima</s0><s2>FE</s2></fC07><fC07 i1="06" i2="X" l="FRE"><s0>Virus immunodéficience humaine</s0><s2>NW</s2></fC07><fC07 i1="06" i2="X" l="ENG"><s0>Human immunodeficiency virus</s0><s2>NW</s2></fC07><fC07 i1="06" i2="X" l="SPA"><s0>Human immunodeficiency virus</s0><s2>NW</s2></fC07><fC07 i1="07" i2="X" l="FRE"><s0>Lentivirus</s0><s2>NW</s2></fC07><fC07 i1="07" i2="X" l="ENG"><s0>Lentivirus</s0><s2>NW</s2></fC07><fC07 i1="07" i2="X" l="SPA"><s0>Lentivirus</s0><s2>NW</s2></fC07><fC07 i1="08" i2="X" l="FRE"><s0>Retroviridae</s0><s2>NW</s2></fC07><fC07 i1="08" i2="X" l="ENG"><s0>Retroviridae</s0><s2>NW</s2></fC07><fC07 i1="08" i2="X" l="SPA"><s0>Retroviridae</s0><s2>NW</s2></fC07><fC07 i1="09" i2="X" l="FRE"><s0>Virus</s0><s2>NW</s2></fC07><fC07 i1="09" i2="X" l="ENG"><s0>Virus</s0><s2>NW</s2></fC07><fC07 i1="09" i2="X" l="SPA"><s0>Virus</s0><s2>NW</s2></fC07><fN21><s1>143</s1></fN21><fN44 i1="01"><s1>PSI</s1></fN44><fN82><s1>PSI</s1></fN82></pA></standard></inist><affiliations><list><country><li>Japon</li></country><region><li>Région du Kansai</li></region><settlement><li>Kyoto</li></settlement><orgName><li>Université de Kyoto</li></orgName></list><tree><country name="Japon"><noRegion><name sortKey="Masuda, Naoyuki" sort="Masuda, Naoyuki" uniqKey="Masuda N" first="Naoyuki" last="Masuda">Naoyuki Masuda</name></noRegion><name sortKey="Baba, Masanori" sort="Baba, Masanori" uniqKey="Baba M" first="Masanori" last="Baba">Masanori Baba</name><name sortKey="Fujii, Masahiro" sort="Fujii, Masahiro" uniqKey="Fujii M" first="Masahiro" last="Fujii">Masahiro Fujii</name><name sortKey="Fujiwara, Masatoshi" sort="Fujiwara, Masatoshi" uniqKey="Fujiwara M" first="Masatoshi" last="Fujiwara">Masatoshi Fujiwara</name><name sortKey="Fujiyasu, Jiro" sort="Fujiyasu, Jiro" uniqKey="Fujiyasu J" first="Jiro" last="Fujiyasu">Jiro Fujiyasu</name><name sortKey="Hatta, Toshifumi" sort="Hatta, Toshifumi" uniqKey="Hatta T" first="Toshifumi" last="Hatta">Toshifumi Hatta</name><name sortKey="Inoue, Hiroshi" sort="Inoue, Hiroshi" uniqKey="Inoue H" first="Hiroshi" last="Inoue">Hiroshi Inoue</name><name sortKey="Kageyama, Shunji" sort="Kageyama, Shunji" uniqKey="Kageyama S" first="Shunji" last="Kageyama">Shunji Kageyama</name><name sortKey="Kodama, Eiichi" sort="Kodama, Eiichi" uniqKey="Kodama E" first="Eiichi" last="Kodama">Eiichi Kodama</name><name sortKey="Koga, Hironobu" sort="Koga, Hironobu" uniqKey="Koga H" first="Hironobu" last="Koga">Hironobu Koga</name><name sortKey="Kontani, Toru" sort="Kontani, Toru" uniqKey="Kontani T" first="Toru" last="Kontani">Toru Kontani</name><name sortKey="Kurihara, Hiroyuki" sort="Kurihara, Hiroyuki" uniqKey="Kurihara H" first="Hiroyuki" last="Kurihara">Hiroyuki Kurihara</name><name sortKey="Matsuoka, Masao" sort="Matsuoka, Masao" uniqKey="Matsuoka M" first="Masao" last="Matsuoka">Masao Matsuoka</name><name sortKey="Moritomo, Ayako" sort="Moritomo, Ayako" uniqKey="Moritomo A" first="Ayako" last="Moritomo">Ayako Moritomo</name><name sortKey="Ohgami, Tetsuro" sort="Ohgami, Tetsuro" uniqKey="Ohgami T" first="Tetsuro" last="Ohgami">Tetsuro Ohgami</name><name sortKey="Ohta, Mitsuaki" sort="Ohta, Mitsuaki" uniqKey="Ohta M" first="Mitsuaki" last="Ohta">Mitsuaki Ohta</name><name sortKey="Orita, Masaya" sort="Orita, Masaya" uniqKey="Orita M" first="Masaya" last="Orita">Masaya Orita</name><name sortKey="Shigeta, Shiro" sort="Shigeta, Shiro" uniqKey="Shigeta S" first="Shiro" last="Shigeta">Shiro Shigeta</name><name sortKey="Shimizu, Yasuaki" sort="Shimizu, Yasuaki" uniqKey="Shimizu Y" first="Yasuaki" last="Shimizu">Yasuaki Shimizu</name><name sortKey="Shintani, Masafumi" sort="Shintani, Masafumi" uniqKey="Shintani M" first="Masafumi" last="Shintani">Masafumi Shintani</name><name sortKey="Sudo, Kenji" sort="Sudo, Kenji" uniqKey="Sudo K" first="Kenji" last="Sudo">Kenji Sudo</name><name sortKey="Suzuki, Hiroshi" sort="Suzuki, Hiroshi" uniqKey="Suzuki H" first="Hiroshi" last="Suzuki">Hiroshi Suzuki</name><name sortKey="Yamamoto, Osamu" sort="Yamamoto, Osamu" uniqKey="Yamamoto O" first="Osamu" last="Yamamoto">Osamu Yamamoto</name><name sortKey="Yokota, Tomoyuki" sort="Yokota, Tomoyuki" uniqKey="Yokota T" first="Tomoyuki" last="Yokota">Tomoyuki Yokota</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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