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Structure-activity relationship studies of 1-(1 '-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses
Li, G (Li, Gen); Zhao, JY (Zhao, Jiang-Yu); Niu, C (Niu, Chao); Nie, LF (Nie, Li-Fei); Dong, CZ (Dong, Chang-Zhi); Aisa, HA (Aisa, Haji Akber)
2017
Source PublicationBIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN0960-894X
Volume27Issue:6Pages:1484-1487
Abstract

A series of 1-(1'-hydroxyalkyl)rupestonic acid methyl esters were synthesized via the condensation of methyl rupestonate with various aldehydes in the presence of LDA. This mixed aldol reaction was highly stereoselective and all the new compounds were elucidated by detailed NMR and MS analyses. The absolute configurations of the newly formed stereocenters were further confirmed by X-ray crystallographic analysis of 3d, the results of which were found to be opposite to the prediction based on Zimmerman-Traxler's and Houk's models. All the compounds synthesized were then evaluated for their in vitro inhibitory activities against influenza A (H1N1 and H3N2) and B viruses. The data showed that 3p displayed the highest activity against influenza A H1N1 (IC50 = 0.69 mu g/mL) and H3N2 (IC50= 0.69 mu g/mL) viruses, which were even better than Ribavirin and Oseltmivir. On the other hand, both 3c and 30 were found to show comparable activities with the reference drugs in inhibiting both influenza A and B viruses. Further studies will focus on reducing the cytotoxicity of the hits reported in this work.

KeywordRupestonic Acid Synthesis X-ray Crystallographic Analysis Anti-influenza Viruses
DOI10.1016/j.bmcl.2016.06.011
Indexed BySCI
WOS IDWOS:000396798800029
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Document Type期刊论文
Identifierhttp://ir.xjipc.cas.cn/handle/365002/4781
Collection省部共建新疆特有药用资源利用重点实验室
资源化学研究室
Corresponding AuthorAisa, HA (Aisa, Haji Akber)
Affiliation1.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, Key Lab Plant Resources & Chem Arid Zone, Urumqi 830011, Peoples R China
2.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, State Key Lab Basis Xinjiang Indigenous Med Plant, Urumqi 830011, Peoples R China
3.Univ Paris Diderot, CNRS, Sorbonne Paris Cite, ITODYS,UMR 7086, 15 Rue J-A Baif, F-75205 Paris 13, France
Recommended Citation
GB/T 7714
Li, G ,Zhao, JY ,Niu, C ,et al. Structure-activity relationship studies of 1-(1 '-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,2017,27(6):1484-1487.
APA Li, G ,Zhao, JY ,Niu, C ,Nie, LF ,Dong, CZ ,&Aisa, HA .(2017).Structure-activity relationship studies of 1-(1 '-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses.BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,27(6),1484-1487.
MLA Li, G ,et al."Structure-activity relationship studies of 1-(1 '-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses".BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 27.6(2017):1484-1487.
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