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1,2,3-Triazole-containing derivatives of rupestonic acid: Click-chemical synthesis and antiviral activities against influenza viruses
He, Yao-Wu; Dong, Chang-Zhi; Zhao, Jiang-Yu; Ma, Lin-Lin; Li, Yu-Huan; Aisa, Haji Akber
2014
Source PublicationEUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
ISSN0223-5234
Volume76Issue:4Pages:245-255
Abstract

Two series of rupestonic acid derivatives, (1-substituted-1H-1,2,3-triazol-4-yl)methyl 2-((5R,8S,8aS)-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl)acrylate and N-(1-substituted-1H-1,2,3-triazol-4-yl)methyl 2-((5R,8S,8aS)-3,8-dimethyl-2-oxo-1,2,4,5,6,7,8,8a-octahydroazulen-5-yl)acrylamide were easily and efficiently synthesized via click chemistry. These compounds were tested for their in vitro activities against various strains of influenza A virus (H1N1, oseltamivir resistant H1N1, H3N2) and influenza B virus. The results showed that nine compounds were active against the H1N1 strain of influenza A virus and among them the best one 14a, was as active as the reference drugs, Oseltamivir and Ribavirin. Some of them were also active on the Oseltamivir resistant H1N1 strain. In regards to influenza B virus, twenty-one compounds over thirty were active and seven of them 7b, 8b, 9b, 10a, 11b, 12b, 13b showed better activity than Ribavirin. The structure-activity relationship of these compounds is discussed on the basis of each type of the viruses studied. Furthermore, four best representative compounds 7b, 10a, 12b and 14a were evaluated in a plaque assay experiment using MDCK cells and RBV as control compound and the results showed that 7b, 10a and 12b were better than RBV in inhibiting plaque formation, in good accordance with their anti-influenza B activities.

KeywordRupestonic Acid Click Chemistry 1 Influenza Virus 2 3-triazole
DOI10.1016/j.ejmech.2014.02.029
Indexed BySCI
WOS IDWOS:000335487400021
Citation statistics
Document Type期刊论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/3789
Collection省部共建新疆特有药用资源利用重点实验室
AffiliationChinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Reg, Urumqi 830011, Xinjiang, Peoples R China;Univ Paris Diderot, Sorbonne Paris Cite, ITODYS, UMR 7086,CNRS, F-75205 Paris 13, France;Guangdong Univ Technol, Sch Light Ind & Chem Engn, Guangzhou 510006, Guangdong, Peoples R China;Chinese Acad Med Sci, Inst Med Biotechnol, Beijing 100050, Peoples R China;Peking Union Med Coll, Beijing 100050, Peoples R China
Recommended Citation
GB/T 7714
He, Yao-Wu,Dong, Chang-Zhi,Zhao, Jiang-Yu,et al. 1,2,3-Triazole-containing derivatives of rupestonic acid: Click-chemical synthesis and antiviral activities against influenza viruses[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2014,76(4):245-255.
APA He, Yao-Wu,Dong, Chang-Zhi,Zhao, Jiang-Yu,Ma, Lin-Lin,Li, Yu-Huan,&Aisa, Haji Akber.(2014).1,2,3-Triazole-containing derivatives of rupestonic acid: Click-chemical synthesis and antiviral activities against influenza viruses.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,76(4),245-255.
MLA He, Yao-Wu,et al."1,2,3-Triazole-containing derivatives of rupestonic acid: Click-chemical synthesis and antiviral activities against influenza viruses".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 76.4(2014):245-255.
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