-Drug Synthesis Database

【结构式】

【药物名称】

【化学名称】3-[(1R,4S,5R,8S,9R,12R,13R)-1,5,9-Trimethyl-10-oxo-14,15,16-trioxa-11-azatetracyclo[10.3.1.0(4,13).0(8,13)]hexadec-11-yl]prop-2(E)-enoic acid methyl ester
　　　　　　(3R,5aS,6R,8aS,9R,12R,12aR)-3-(3,6,9-Trimethyl-10-oxoperhydro-3,12-epoxy-1,2-dioxepino[4,3-i]isoquinolin-11-yl)-2(E)-propenoic acid methyl ester
　　　　　　11-[3-Methoxy-3-oxo-1(E)-propen-1-yl]-11-azaartemisinin

【CA登记号】

【分子式】C₁₉H₂₇NO₆

【分子量】365.43014

【开发单位】National Institutes of Health (Originator), Walter Reed Army Institute (Originator)

【药理作用】ANTIINFECTIVE THERAPY, Antimalarials, Treatment of Protozoal Diseases

合成路线1

11-Azaartemisinin (II) was prepared from artemisinin (I) by reaction with methanolic ammonia, followed by acid treatment. Then, conjugate addition of methyl propiolate (III) to 11-azaartemisinin (II) in the presence of dimethylaminopyridine furnished the title compound.

参考文献中间体

【1】 Katz, E.; et al.; Structure and antimalarial activity of adducts of 11-azaartemisinin with conjugated terminal acetylenes. Bioorg Med Chem Lett 1999, 9, 20, 2969.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	22369	Qinghaosu; Artemisine; (1R,4S,5R,8S,9R,12S,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecan-10-one	63968-64-9	C₁₅H₂₂O₅	详情	详情
(II)	38763	(1R,4S,5R,8S,9R,12R,13R)-1,5,9-trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0(4,13).0(8,13)]hexadecan-10-one		C₁₅H₂₃NO₄	详情	详情
(III)	19588	methyl propiolate	922-67-8	C₄H₄O₂	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)