Canfosfamide hydrochloride, TLK-286, TER-286, Telcyta
(2R)-L-gamma-谷氨酰-3-((2-((二(二(2-氯乙基)氨基)亚膦酰)氧基)乙基)磺酰基)-L-丙氨酰-2-苯基甘氨酸 Chemical Name: 2(R)-[2-[4(S)-Amino-4-carboxybutyramido]-3-[2(R)-[bis[N,N-bis(2-chloroethyl)amino]phosphoryloxy]ethylsulfonyl]propionamido]-2-phenylacetic acid hydrochloride; L-gamma-Glutamyl-3-[2-[bis[bis(2-chloroethyl)amino]phosphinyloxy]ethylsulfonyl]-L-alanyl-2(R)-phenylglycine monohydrochloride
CAS No. 439943-59-6, 158382-37-7 (free base)
项目整合开发状态: Phase III
项目研究机构: Telik (Originator), Taiho (Licensee)
合成路线:The intermediate N,N,N',N'-tetrakis(2-chloroethyl)phosphorodiamidate (IV) was prepared by an improved procedure consisting of addition of phosphoryl chloride to 2-bromoethanol (I) in the presence of Et3N,followed by in situ treatment of the resulting intermediate (II) with bis(2-chloroethyl)amine (III).
合成路线:The known gamma-glutamyl-(S-benzylcysteinyl)-(R)-(-)-phenylglycine (V) was debenzylated to the corresponding thiol (VI) by means of sodium in liquid ammonia.Subsequent S-alkylation of (VI) with bromide (III) produced thioether (VII),which was finally oxidized to the title sulfone employing peracetic acid.
📌 参考资料/链接：
参考文献标题:Glutathione S-transferase-activated cpds.
文献作者:Kauvar,L.; Lyttle,M.H.; Satyam,A.(Telik,Inc.)
参考来源:WO 9509866
📄 详细内容
合成路线:The intermediate N,N,N',N'-tetrakis(2-chloroethyl)phosphorodiamidate (IV) was prepared by an improved procedure consisting of addition of phosphoryl chloride to 2-bromoethanol (I) in the presence of Et3N,followed by in situ treatment of the resulting intermediate (II) with bis(2-chloroethyl)amine (III).
合成路线:The known gamma-glutamyl-(S-benzylcysteinyl)-(R)-(-)-phenylglycine (V) was debenzylated to the corresponding thiol (VI) by means of sodium in liquid ammonia.Subsequent S-alkylation of (VI) with bromide (III) produced thioether (VII),which was finally oxidized to the title sulfone employing peracetic acid.
参考文献标题:Glutathione-S-transferase activates novel alkylating agents
文献作者:Lyttle,M.H.; Satyam,A.; Hocker,M.D.; Bauer,K.E.; Caldwell,C.G.; Hui,H.C.; Morgan,A.S.; Mergia,A.; Kauvar,L.M.
参考来源:J Med Chem 1994,37(10),1501
产品链接: CAS No. 439943-59-6›› 产品链接: CAS No.158382-37-7››