Structure-activity relationship studies of 1-(1 '-hydroxyalkyl)rupestonic acid methyl esters against influenza viruses

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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)
刊名	BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
	2017
卷号	27 期号:6 页码:1484-1487
关键词	Rupestonic acid Synthesis X-ray crystallographic analysis Anti-influenza viruses
通讯作者	Aisa, HA
英文摘要	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.
收录类别	SCI
WOS记录号	WOS:000396798800029
内容类型	期刊论文
源URL	[http://ir.xjipc.cas.cn/handle/365002/4781]
专题	新疆理化技术研究所_省部共建新疆特有药用资源利用重点实验室新疆理化技术研究所_资源化学研究室
作者单位	1.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
推荐引用方式 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.