Ambamustine hydrochloride, PTT-119
乙基(2S,5S)-5-[[(2S)-2-氨基-3-(4-氟苯基)丙烷酰]氨基]-6-[3-[双苯(2-氯乙基)氨基]苯基]-2-(2-甲基磺酰乙基)-4-氧己酸盐盐酸盐 氨莫司汀 Chemical Name: 3-(4-Fluorophenyl)-L-alanyl-3-[3-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionine ethyl ester hydrochloride; 4-Fluoro-L-phenylalanyl-3-[bis(2-chloroethyl)amino]-L-alanyl-L-methionine ethyl ester hydrochloride; N-[3-[3-[Bis(2-chloroethyl)amino]phenyl]-N-[3-(4-fluorophenyl)-L-alanyl]-L-alanyl]-L-methionine ethyl ester hydrochloride
CAS No. 83996-50-3, 85754-59-2 (free base)
项目整合开发状态: Registered-1993
项目研究机构: Proter (Originator)
合成路线:The condensation of N-formyl-4-fluorophenylalanine (I) with 3-[bis(2-chloroethyl)amino]phenylalanine ethyl ester (II) by means of dicyclohexylcarbodiimide in THF gives N-formyl-4-fluoro-L-phenylalanyl-3-[bis(2-chloroethyl)amino]-L-phenylalanine ethyl ester (III),which is saponified with NaOH in DMF water yielding the free acid (IV).The condensation of (IV) with L-methionine ethyl ester (V) by means of N-hydroxysuccinimide and dicyclohexylcarbodiimide in DMF affords N-formyl-4-fluoro-L-phenylalanyl-3-[bis(2-chloroethyl)amino]phenylalanyl-L-methionine ethyl ester (VI),which is finally deprotected by elimination of the formyl group in ethanolic HCl.
📌 参考资料/链接：
参考文献标题:PTT-119
文献作者:Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1984,9(10),753
📄 详细内容
合成路线:The condensation of N-formyl-4-fluorophenylalanine (I) with 3-[bis(2-chloroethyl)amino]phenylalanine ethyl ester (II) by means of dicyclohexylcarbodiimide in THF gives N-formyl-4-fluoro-L-phenylalanyl-3-[bis(2-chloroethyl)amino]-L-phenylalanine ethyl ester (III),which is saponified with NaOH in DMF water yielding the free acid (IV).The condensation of (IV) with L-methionine ethyl ester (V) by means of N-hydroxysuccinimide and dicyclohexylcarbodiimide in DMF affords N-formyl-4-fluoro-L-phenylalanyl-3-[bis(2-chloroethyl)amino]phenylalanyl-L-methionine ethyl ester (VI),which is finally deprotected by elimination of the formyl group in ethanolic HCl.
参考文献标题:Compounds of dichlorodiethylaminophenylalanine with anti-tumor activity
文献作者:De Barbieri,A.
参考来源:EP 0056565; ES 8206449; IT 1134503; JP 57120559; US 4428875
合成路线:The condensation of N-formyl-4-fluorophenylalanine (I) with 3-[bis(2-chloroethyl)amino]phenylalanine ethyl ester (II) by means of dicyclohexylcarbodiimide in THF gives N-formyl-4-fluoro-L-phenylalanyl-3-[bis(2-chloroethyl)amino]-L-phenylalanine ethyl ester (III),which is saponified with NaOH in DMF water yielding the free acid (IV).The condensation of (IV) with L-methionine ethyl ester (V) by means of N-hydroxysuccinimide and dicyclohexylcarbodiimide in DMF affords N-formyl-4-fluoro-L-phenylalanyl-3-[bis(2-chloroethyl)amino]phenylalanyl-L-methionine ethyl ester (VI),which is finally deprotected by elimination of the formyl group in ethanolic HCl.
参考文献标题:Synthesis,acute toxicity and chemotherapeutic anti-cancer activities of a new tripeptidic mustard
文献作者:De Barbieri,A.; et al.
参考来源:Farm Sci Ed 1983,38(4),205-218
产品链接: CAS No. 83996-50-3›› 产品链接: CAS No.85754-59-2››