Chemical Name: gamma-L-Glutamyl-L-[S-[N-(4-chlorophenyl)-N-hydroxycarbamoyl]]cysteinyl-glycine diethyl ester hydrochloride; S-[N-(4-chlorophenyl)-N-hydroxycarbamoyl]glutathione diethyl ester hydrochloride
CAS No. 174568-91-3 (free base)
项目整合开发状态: Preclinical
项目研究机构: University of Maryland (Originator)
合成路线:Treatment of 4-chlorophenyl chloroformate (I) with N-(4-chlorophenyl) hydroxylamine (II) produced the N-hydroxycarbamate (III).This was condensed with glutathione (IV) to afford thiocarbamate (V).Finally,both carboxylate groups of (V) were esterified in ethanolic HCl to provide the target diethyl ester.
📄 详细内容
合成路线:Treatment of 4-chlorophenyl chloroformate (I) with N-(4-chlorophenyl) hydroxylamine (II) produced the N-hydroxycarbamate (III).This was condensed with glutathione (IV) to afford thiocarbamate (V).Finally,both carboxylate groups of (V) were esterified in ethanolic HCl to provide the target diethyl ester.
参考文献标题:Mechanism-based competitive inhibitors of glyoxalase I: Intracellular delivery,in vitro antitumor activities,and stabilities in human serum and mouse serum
文献作者:Kavarana,M.J.; Kovaleva,E.G.; Creighton,D.J.; Wollman,M.B.; Eiseman,J.L.
参考来源:J Med Chem 1999,42(2),221
合成路线:Treatment of 4-chlorophenyl chloroformate (I) with N-(4-chlorophenyl) hydroxylamine (II) produced the N-hydroxycarbamate (III).This was condensed with glutathione (IV) to afford thiocarbamate (V).Finally,both carboxylate groups of (V) were esterified in ethanolic HCl to provide the target diethyl ester.
参考文献标题:S-(N-Aryl-N-hydroxycarbamoyl)glutathione derivatives are tight-binding inhibitors of Glyoxalase I and Slow Substrates for Glyoxalase II
文献作者:Muthy,N.S.R.K.
参考来源:J Med Chem 1994,37(14),2161-2166
合成路线:Treatment of 4-chlorophenyl chloroformate (I) with N-(4-chlorophenyl) hydroxylamine (II) produced the N-hydroxycarbamate (III).This was condensed with glutathione (IV) to afford thiocarbamate (V).Finally,both carboxylate groups of (V) were esterified in ethanolic HCl to provide the target diethyl ester.
参考文献标题:Pharmacokinetics and antitumor properties in tumor-bearing mice of an enediol analogue inhibitor of glyoxalase I
文献作者:Sharkey,E.M.; O'Neill,H.B.; Kavarana,M.J.; Wang,H.; Creighton,D.J.; Sentz,D.L.; Eiseman,J.L.
参考来源:Cancer Chemotherapy and Pharmacology 2000,46(2),156