CKD-731
Chemical Name: 3-(3,4,5-Trimethoxyphenyl)-2(E)-propenoic acid (3R,4S,5S,6R)-4-[2(R)-methyl-3(R)-(3-methyl-2-butenyl)oxiran-2-yl]-5-methoxy-1-oxaspiro[2.5]oct-6-yl ester; 6-O-[3-(3,4,5-Trimethoxyphenyl)-2(E)-propenoyl]fumagillol
CAS No. 251111-15-6
项目整合开发状态: Preclinical
项目研究机构: Chong Kun Dang Pharm. (Originator)
合成路线:Treatment of 3,4,5-trimethoxycinnamic acid (I) with oxalyl chloride and pyridine produced acid chloride (II).This was then coupled with fumagillol (III),an hydrolyzed product of the fungal metabolite fumagillin,in the presence of NaH in THF to give the title trimethoxycinnamyl ester.Alternatively,fumagillol (III) was coupled with acid anhydride (IV) using DMAP in CH2Cl2.
合成路线:4-(2-Dimethylaminoethoxy)cinnamic acid (I) was converted to acid chloride (II) upon treatment with thionyl chloride in refluxing benzene.This was then coupled with the sodium alkoxide of fumagillol (III) in THF to furnish the title compound.
📌 参考资料/链接：
参考文献标题:Fumagillol derivs.and processes for preparing the same
文献作者:Chun,H.S.; Choi,N.S.; Lee,S.J.; Han,C.K.; Hong,C.I.; Hong,R.K.; Kim,J.W.; Moon,S.K.; Ahn,S.K.(Chong Kun Dang Corp.)
参考来源:US 6063812; WO 9959986
📄 详细内容
合成路线:Treatment of 3,4,5-trimethoxycinnamic acid (I) with oxalyl chloride and pyridine produced acid chloride (II).This was then coupled with fumagillol (III),an hydrolyzed product of the fungal metabolite fumagillin,in the presence of NaH in THF to give the title trimethoxycinnamyl ester.Alternatively,fumagillol (III) was coupled with acid anhydride (IV) using DMAP in CH2Cl2.
参考文献标题:Design and synthesis of highly potent fumagillin analogues from homology modeling for a human MetAP-2
文献作者:Han,C.K.; Ahn,S.K.; Choi,N.S.; Hong,R.K.; Moon,S.K.; Chun,H.S.; Lee,S.J.; Kim,J.W.; Hong,C.I.; Kim,D.; Yoon,J.H.; No,K.T.
参考来源:Bioorg Med Chem Lett 2000,10(1),39
合成路线:Treatment of 3,4,5-trimethoxycinnamic acid (I) with oxalyl chloride and pyridine produced acid chloride (II).This was then coupled with fumagillol (III),an hydrolyzed product of the fungal metabolite fumagillin,in the presence of NaH in THF to give the title trimethoxycinnamyl ester.Alternatively,fumagillol (III) was coupled with acid anhydride (IV) using DMAP in CH2Cl2.
参考文献标题:Synthesis of novel fumagillin analogs as antiangiogenic agents
文献作者:Griffith,E.C.; Dai,X.B.; Liu,J.O.
参考来源:219th ACS Natl Meet (March 26 2000,San Francisco) 2000,Abst MEDI 61
产品链接: CAS No. 251111-15-6››