ICI-155387, CB-3717
Chemical Name: N-[4-[[(2-Amino-1,4-dihydro-4-oxo-6-quinazolinyl)methyl]-2-propynylamino]benzoyl]-L-glutamic acid; N-[4-[N-[(2-Amino-4-hydroxy-6-quinazolinyl)methyl]prop-2-ynylamino]benzoyl]-L-glutamic acid; N10-Propargyl-5,8-dideazafolic acid
CAS No. 76849-19-9
项目整合开发状态: Phase II
项目研究机构: AstraZeneca (Originator), Pfizer (Originator)
合成路线:The alkylation of diethyl N-(4-aminobenzoyl)glutamate (I) with propargyl bromide (II) in hot ethanol gives diethyl N-[4-(propargylamino)benzoyl]glutamate (III),which is condensed with 2-amino-6-bromomethyl-4-hydroxyquinazoline (IV) by means of triethylamine in hot 2-ethoxyethanol (or CaCO3 in dimethylacetamide) yielding diethyl N-[4-[N-[(2-amino-4-hydroxy-6-quinazolinyl)methyl]prop-2-ynylamino]benzoyl]-L-glutamate (V).Finally,this compound is saponified with NaOH in ethanol-water.
📌 参考资料/链接：
参考文献标题:CB-3717
文献作者:Hopkins,S.J.; Serradell,M.N.; Castar,J.
参考来源:Drugs Fut 1984,9(12),893
📄 详细内容
合成路线:The alkylation of diethyl N-(4-aminobenzoyl)glutamate (I) with propargyl bromide (II) in hot ethanol gives diethyl N-[4-(propargylamino)benzoyl]glutamate (III),which is condensed with 2-amino-6-bromomethyl-4-hydroxyquinazoline (IV) by means of triethylamine in hot 2-ethoxyethanol (or CaCO3 in dimethylacetamide) yielding diethyl N-[4-[N-[(2-amino-4-hydroxy-6-quinazolinyl)methyl]prop-2-ynylamino]benzoyl]-L-glutamate (V).Finally,this compound is saponified with NaOH in ethanol-water.
参考文献标题:Anti-cancer quinazoline derivatives
文献作者:Jones,T.R.; Harrap,K.R.; Calvert,A.H.
参考来源:EP 0031237; GB 2065653; US 4447608; US 4564616
产品链接: CAS No. 76849-19-9››