Design, Synthesis, and Evaluation of 3‐((4‐(t‐Butyl)‐2‐(2‐benzylidenehydrazinyl)thiazol‐5‐yl)methyl)quinolin‐2(1H)‐ones as Neuraminidase Inhibitors
Identifieur interne : 001E14 ( Istex/Curation ); précédent : 001E13; suivant : 001E15Design, Synthesis, and Evaluation of 3‐((4‐(t‐Butyl)‐2‐(2‐benzylidenehydrazinyl)thiazol‐5‐yl)methyl)quinolin‐2(1H)‐ones as Neuraminidase Inhibitors
Auteurs : Yilin Fang [République populaire de Chine] ; Mengwu Xiao [République populaire de Chine] ; Aixi Hu [République populaire de Chine] ; Jiao Ye [République populaire de Chine] ; Wenwen Lian [République populaire de Chine] ; Ailin Liu [République populaire de Chine]Source :
- Chinese Journal of Chemistry [ 1001-604X ] ; 2016-04.
Abstract
A series of novel 3‐((4‐(t‐butyl)‐2‐(2‐benzylidenehydrazinyl)thiazol‐5‐yl)methyl)quinolin‐2(1H)‐ones (7a–7z) were designed, synthesized and evaluated for their ability of inhibiting neuraminidase (NA) of in?uenza H1N1 virus. Some compounds displayed moderate influenza NA inhibitory activity. Compound 7l with the scaffold of 2‐(2‐(2‐methoxybenzylidene)hydrazinyl)thiazole was the best one, exhibiting moderate NA inhibitory activity with IC50 of 44.66 µmol/L. Structure‐activity relationship showed that compounds with methoxy or hydroxy groups at the ortho position, fluorine and nitro groups at the meta position and chlorine and bromine groups at the para position of phenyl ring were more active. Docking study indicated that compound 7l has important interactions with some key residues (including Asp151, Glu119, Arg292, Tyr406, and Asn347) and binds to 430‐cavity adjacent to NA active site.
A series of novel 3‐((4‐(t‐butyl)‐2‐(2‐benzylidenehydrazinyl)thiazol‐5‐yl)methyl)qui‐nolin‐2(1H)‐ones (7a–7z) were designed, syn‐thesized and evaluated for their ability of inhibiting neuraminidase (NA) of influenza H1N1 virus. Compound 7l with the scaffold of 2‐(2‐(2‐methoxybenzylidene)hydrazinyl)thiazole was the best one, exhibiting mod‐erate NA inhibitory activity with IC50 of 44.66 µmol/L.
Url:
DOI: 10.1002/cjoc.201500738
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wicri:level="1"><mods:affiliation>College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, China</mods:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082</wicri:regionArea></affiliation></author><author><name sortKey="Xiao, Mengwu" sort="Xiao, Mengwu" uniqKey="Xiao M" first="Mengwu" last="Xiao">Mengwu Xiao</name><affiliation wicri:level="1"><mods:affiliation>College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, China</mods:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082</wicri:regionArea></affiliation></author><author><name sortKey="Hu, Aixi" sort="Hu, Aixi" uniqKey="Hu A" first="Aixi" last="Hu">Aixi Hu</name><affiliation wicri:level="1"><mods:affiliation>College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, China</mods:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082</wicri:regionArea></affiliation><affiliation wicri:level="1"><mods:affiliation>E-mail: axhu@hnu.edu.cn</mods:affiliation><country wicri:rule="url">République populaire de Chine</country></affiliation><affiliation wicri:level="1"><mods:affiliation>Aixi Hu, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China, Tel./fax: 0086‐0731‐88822286Ailin Liu, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China</mods:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Aixi Hu, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China, Tel./fax: 0086‐0731‐88822286Ailin Liu, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050</wicri:regionArea></affiliation></author><author><name sortKey="Ye, Jiao" sort="Ye, Jiao" uniqKey="Ye J" first="Jiao" last="Ye">Jiao Ye</name><affiliation wicri:level="1"><mods:affiliation>College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082, China</mods:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan 410082</wicri:regionArea></affiliation></author><author><name sortKey="Lian, Wenwen" sort="Lian, Wenwen" uniqKey="Lian W" first="Wenwen" last="Lian">Wenwen Lian</name><affiliation wicri:level="1"><mods:affiliation>Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China</mods:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050</wicri:regionArea></affiliation></author><author><name sortKey="Liu, Ailin" sort="Liu, Ailin" uniqKey="Liu A" first="Ailin" last="Liu">Ailin Liu</name><affiliation wicri:level="1"><mods:affiliation>Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China</mods:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050</wicri:regionArea></affiliation><affiliation wicri:level="1"><mods:affiliation>E-mail: liuailin@imm.ac.cn</mods:affiliation><country wicri:rule="url">République populaire de Chine</country></affiliation><affiliation wicri:level="1"><mods:affiliation>Aixi Hu, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China, Tel./fax: 0086‐0731‐88822286Ailin Liu, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China</mods:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Aixi Hu, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China, Tel./fax: 0086‐0731‐88822286Ailin Liu, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050</wicri:regionArea></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Chinese Journal of Chemistry</title><title level="j" type="alt">CHINESE JOURNAL OF CHEMISTRY</title><idno type="ISSN">1001-604X</idno><idno type="eISSN">1614-7065</idno><imprint><biblScope unit="vol">34</biblScope><biblScope unit="issue">4</biblScope><biblScope unit="page" from="403">403</biblScope><biblScope unit="page" to="411">411</biblScope><biblScope unit="page-count">9</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2016-04">2016-04</date></imprint><idno type="ISSN">1001-604X</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1001-604X</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A series of novel 3‐((4‐(t‐butyl)‐2‐(2‐benzylidenehydrazinyl)thiazol‐5‐yl)methyl)quinolin‐2(1H)‐ones (7a–7z) were designed, synthesized and evaluated for their ability of inhibiting neuraminidase (NA) of in?uenza H1N1 virus. Some compounds displayed moderate influenza NA inhibitory activity. Compound 7l with the scaffold of 2‐(2‐(2‐methoxybenzylidene)hydrazinyl)thiazole was the best one, exhibiting moderate NA inhibitory activity with IC50 of 44.66 µmol/L. Structure‐activity relationship showed that compounds with methoxy or hydroxy groups at the ortho position, fluorine and nitro groups at the meta position and chlorine and bromine groups at the para position of phenyl ring were more active. Docking study indicated that compound 7l has important interactions with some key residues (including Asp151, Glu119, Arg292, Tyr406, and Asn347) and binds to 430‐cavity adjacent to NA active site.</div><div type="abstract" xml:lang="en">A series of novel 3‐((4‐(t‐butyl)‐2‐(2‐benzylidenehydrazinyl)thiazol‐5‐yl)methyl)qui‐nolin‐2(1H)‐ones (7a–7z) were designed, syn‐thesized and evaluated for their ability of inhibiting neuraminidase (NA) of influenza H1N1 virus. Compound 7l with the scaffold of 2‐(2‐(2‐methoxybenzylidene)hydrazinyl)thiazole was the best one, exhibiting mod‐erate NA inhibitory activity with IC50 of 44.66 µmol/L.</div></front></TEI></record>Pour manipuler ce document sous Unix (Dilib)
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