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 : 004D56 ( Main/Exploration ); précédent : 004D55; suivant : 004D57Studies 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
- KwdFr :
- Humains, Inhibiteurs de la transcriptase inverse (), Inhibiteurs de la transcriptase inverse (pharmacologie), Inhibiteurs de la transcriptase inverse (synthèse chimique), Lignée cellulaire, Relation structure-activité, Spectrométrie de masse FAB, Spectroscopie par résonance magnétique, Sulfonamides (), Sulfonamides (pharmacologie), Sulfonamides (synthèse chimique), Tests de sensibilité microbienne, VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ().
- MESH :
- pharmacologie : Inhibiteurs de la transcriptase inverse, Sulfonamides.
- synthèse chimique : Inhibiteurs de la transcriptase inverse, Sulfonamides.
- Pascal (Inist)
- Humains, Inhibiteurs de la transcriptase inverse, Lignée cellulaire, Relation structure activité, Relation structure-activité, Spectrométrie de masse FAB, Spectroscopie par résonance magnétique, Sulfonamides, Synthèse chimique, Sulfonamide, Tests de sensibilité microbienne, Thiazole dérivé, Nitrile, Benzène dérivé, Hétérocycle soufre azote, Composé non nucléoside, Inhibiteur enzyme, Inhibiteur reverse transcriptase, RNA-directed DNA polymerase, Antiviral, VIH-1 (Virus de l'Immunodéficience Humaine de type 1), 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 :
- Antiviral, Benzene derivatives, Cell Line, Chemical synthesis, Enzyme inhibitor, HIV-1 (drug effects), HIV-1 virus, Humans, In vitro, Magnetic Resonance Spectroscopy, Microbial Sensitivity Tests, Nitrile, Non nucleoside compound, RNA-directed DNA polymerase, Reverse Transcriptase Inhibitors (chemical synthesis), Reverse Transcriptase Inhibitors (chemistry), Reverse Transcriptase Inhibitors (pharmacology), Reverse transcriptase inhibitor, Spectrometry, Mass, Fast Atom Bombardment, Structure activity relation, Structure-Activity Relationship, Sulfonamide, Sulfonamides (chemical synthesis), Sulfonamides (chemistry), Sulfonamides (pharmacology), Sulfur nitrogen heterocycle, Thiazole derivatives.
- MESH :
- chemical , chemical synthesis : Reverse Transcriptase Inhibitors, Sulfonamides.
- chemical , chemistry : Reverse Transcriptase Inhibitors, Sulfonamides.
- drug effects : HIV-1.
- chemical , pharmacology : Reverse Transcriptase Inhibitors, Sulfonamides.
- Cell Line, Humans, Magnetic Resonance Spectroscopy, Microbial Sensitivity Tests, Spectrometry, Mass, Fast Atom Bombardment, Structure-Activity Relationship.
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.
Affiliations:
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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 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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>Cell Line</term><term>Chemical synthesis</term><term>Enzyme inhibitor</term><term>HIV-1 (drug effects)</term><term>HIV-1 virus</term><term>Humans</term><term>In vitro</term><term>Magnetic Resonance Spectroscopy</term><term>Microbial Sensitivity Tests</term><term>Nitrile</term><term>Non nucleoside compound</term><term>RNA-directed DNA polymerase</term><term>Reverse Transcriptase Inhibitors (chemical synthesis)</term><term>Reverse Transcriptase Inhibitors (chemistry)</term><term>Reverse Transcriptase Inhibitors (pharmacology)</term><term>Reverse transcriptase inhibitor</term><term>Spectrometry, Mass, Fast Atom Bombardment</term><term>Structure activity relation</term><term>Structure-Activity Relationship</term><term>Sulfonamide</term><term>Sulfonamides (chemical synthesis)</term><term>Sulfonamides (chemistry)</term><term>Sulfonamides (pharmacology)</term><term>Sulfur nitrogen heterocycle</term><term>Thiazole derivatives</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Humains</term><term>Inhibiteurs de la transcriptase inverse ()</term><term>Inhibiteurs de la transcriptase inverse (pharmacologie)</term><term>Inhibiteurs de la transcriptase inverse (synthèse chimique)</term><term>Lignée cellulaire</term><term>Relation structure-activité</term><term>Spectrométrie de masse FAB</term><term>Spectroscopie par résonance magnétique</term><term>Sulfonamides ()</term><term>Sulfonamides (pharmacologie)</term><term>Sulfonamides (synthèse chimique)</term><term>Tests de sensibilité microbienne</term><term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Reverse Transcriptase Inhibitors</term><term>Sulfonamides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Reverse Transcriptase Inhibitors</term><term>Sulfonamides</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>HIV-1</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Inhibiteurs de la transcriptase inverse</term><term>Sulfonamides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Reverse Transcriptase Inhibitors</term><term>Sulfonamides</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Inhibiteurs de la transcriptase inverse</term><term>Sulfonamides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Cell Line</term><term>Humans</term><term>Magnetic Resonance Spectroscopy</term><term>Microbial Sensitivity Tests</term><term>Spectrometry, Mass, Fast Atom Bombardment</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="Pascal" xml:lang="fr"><term>Humains</term><term>Inhibiteurs de la transcriptase inverse</term><term>Lignée cellulaire</term><term>Relation structure activité</term><term>Relation structure-activité</term><term>Spectrométrie de masse FAB</term><term>Spectroscopie par résonance magnétique</term><term>Sulfonamides</term><term>Synthèse chimique</term><term>Sulfonamide</term><term>Tests de sensibilité microbienne</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>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</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><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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