Baker's triazine antifolate, Triazinate, TZT, NSC-139105
三嗪苯酰胺Chemical Name: 1-[3-Chloro-4-(m-dimethylcarbamoylbenzyloxy)phenyl]-4,6-diamino-1,2-dihydro-2,2-dimethyl-s-triazine monoethanesulfonate; 3-[[2-Chloro-4-(4,6-diamino-2,2-dimethyl-1,3,5-triazin-1(2H)-yl)phenoxy]methyl]-N,N-dimethylbenzamide monoethanesulfonate
CAS No. 41191-04-2
项目整合开发状态: Phase II
项目研究机构: Dept. of Health, Education and Welfare (Originator)
合成路线:The key intermediate alpha-(2-chloro-4-nitrophenoxy)-m-toluic acid (IV) is prepared from methyl m-toluate (I) by bromination with N-bromosuccinimide in the presence of benzoyl peroxide,then condensation with 2-chloro-4-nitrophenol,followed by basic hydrolysis.The carboxylic acid group of compound (IV) is converted to dimethylamide (VI) via acyl chloride (V).The nitro intermediate (VI) is hydrogenated over platinum oxide in 2-methoxyethanol.The resulting amine (VII) is then condensed with cyanoguanidine and acetone in the presence of ethanesulfonic acid to give triazinate.
📌 参考资料/链接：
参考文献标题:TRIAZINATE
文献作者:Chang,P.
参考来源:Drugs Fut 1989,14(2),138
📄 详细内容
合成路线:The key intermediate alpha-(2-chloro-4-nitrophenoxy)-m-toluic acid (IV) is prepared from methyl m-toluate (I) by bromination with N-bromosuccinimide in the presence of benzoyl peroxide,then condensation with 2-chloro-4-nitrophenol,followed by basic hydrolysis.The carboxylic acid group of compound (IV) is converted to dimethylamide (VI) via acyl chloride (V).The nitro intermediate (VI) is hydrogenated over platinum oxide in 2-methoxyethanol.The resulting amine (VII) is then condensed with cyanoguanidine and acetone in the presence of ethanesulfonic acid to give triazinate.
参考文献标题:Irreversible enzyme inhibitors.CLXXIX.Active-site-directed irreversible enzyme inhibitors of dihydrofolate reductase from 1-(3-chlorophenyl)-4,6-diamino-1,2-dihydro-2,2-dimethyl-s-triazine with oxyamine bridges to a terminal sulfonyl flouride
文献作者:Baker,B.R.; Ashton,W.T.
参考来源:J Med Chem 1970,131165-70
合成路线:The key intermediate alpha-(2-chloro-4-nitrophenoxy)-m-toluic acid (IV) is prepared from methyl m-toluate (I) by bromination with N-bromosuccinimide in the presence of benzoyl peroxide,then condensation with 2-chloro-4-nitrophenol,followed by basic hydrolysis.The carboxylic acid group of compound (IV) is converted to dimethylamide (VI) via acyl chloride (V).The nitro intermediate (VI) is hydrogenated over platinum oxide in 2-methoxyethanol.The resulting amine (VII) is then condensed with cyanoguanidine and acetone in the presence of ethanesulfonic acid to give triazinate.
参考文献标题:Water-soluble reversible inhibitors of dihydrofolate reductase with potent antitumor activity derived from 4,6-diamino-1,2-dihydro-2,2-dimethyl-1-phenyl-s-triazine
文献作者:Baker,B.R.; Ashton,W.T.
参考来源:J Med Chem 1973,16209-14
产品链接: CAS No. 41191-04-2››