NSC-127755
贝氏抗叶酸物Chemical Name: 4,6-Diamino-2,2-dimethyl-1-[3-chloro-4-(4-fluorosulfonyl-2-chlorophenylbutyl)phenyl]-s-triazine ethanesulfonate; Ethanesulfonic acid,compound with 3-chloro-4-[4-[2-chloro-4-(4,6-diamino-2,2-dimethyl-s-triazin-1-(2H)-yl)phenyll]butyl]benzenesulfonyl fluoride (1:1)
CAS No. 31368-48-6
项目整合开发状态: Preclinical
项目研究机构: National Cancer Institute (Originator)
合成路线:The reaction of 2-chloro-4-fluorosulfonylbenzyl bromide (I) with triphenylphosphine (II) in refluxing benzene gives the corresponding triphenylphosphonium bromide (III),which is submitted to a Wittig condensation with 2-chloro-4-nitrocinnamaldehyde (IV) [prepared by an aldol condensation of 2-chloro-4-nitrobenzaldehyde (V) and acetaldehyde (VI)] yielding 1-(4-fluorosulfonyl-2-chlorophenyl)-4-(2-chloro-4-nitrophenyl)butadiene (VII).The reduction of (VII) with H2 over PtO2 in methoxyethanol affords 1-(4-fluorosulfonyl-2-chlorophenyl)-4-(2-chloro-4-aminophenyl)butane (VIII),which is finally cyclized with cyanoguanidine (IX) and acetone and treated with ethanesultonic acid.
📌 参考资料/链接：
参考文献标题:NSC-127,755
文献作者:Blancafort,P.; Serradell,M.N.; Castar,J.; Hillier,K.
参考来源:Drugs Fut 1983,8(7),596
📄 详细内容
合成路线:The reaction of 2-chloro-4-fluorosulfonylbenzyl bromide (I) with triphenylphosphine (II) in refluxing benzene gives the corresponding triphenylphosphonium bromide (III),which is submitted to a Wittig condensation with 2-chloro-4-nitrocinnamaldehyde (IV) [prepared by an aldol condensation of 2-chloro-4-nitrobenzaldehyde (V) and acetaldehyde (VI)] yielding 1-(4-fluorosulfonyl-2-chlorophenyl)-4-(2-chloro-4-nitrophenyl)butadiene (VII).The reduction of (VII) with H2 over PtO2 in methoxyethanol affords 1-(4-fluorosulfonyl-2-chlorophenyl)-4-(2-chloro-4-aminophenyl)butane (VIII),which is finally cyclized with cyanoguanidine (IX) and acetone and treated with ethanesultonic acid.
参考文献标题:Irreversible enzyme inhibitors.CLXXVII.Active-site-directed irreversible inhibitos of dihydrofolate reductase derived from 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-(phenylalkylphenyl)-s-triazines
文献作者:Baker,B.R.; Vermeulen,N.M.J.
参考来源:J Med Chem 1970,13(6),1154-60
产品链接: CAS No. 31368-48-6››