Trybizine hydrochloride, SIPI-1029, T-46
Chemical Name: 1',1''-(Hexane-1,6-diyl)bis(oxy)bis(spiro[cyclopentane-1,2'(1'H)-1',3',5'-triazine]-4',6'-diamine) dihydrochloride
CAS No. 172280-69-2, 219325-24-3 (free base)
项目整合开发状态: Preclinical
项目研究机构: Shanghai Inst. Pharm. Ind. (Originator), Xinchang Pharmaceutical Factory (Bulk Supplier)
合成路线:The reaction of benzohydroxamic acid (I) with benzyl bromide (II) by means of NaOH on ethanol gives the corresponding benzyl ester (III),which is treated with HCl yielding O-benzylhydroxylamine (IV).The reaction of (IV) with dicyaniamide (V) in ethanol affords the biguanide (VI),which is cyclized with cyclopentanone (VII) and HCl giving 1-benzyloxy-2,2-dimethyl-1,2-dihydro-1,3,5-triazine-4,6-diamine (VIII).The debenzylation of (VIII) with H2 over PtO2 in ethanol yields 1-hydroxy-2,2-dimethyl-1,2-dihydro-1,3,5-triazine-4,6-diamine (IX),which is finally condensed with 1,6-dibromohexane (X) by means of NaOH in methanol.
合成路线:The reaction of benzohydroxamic acid (I) with 1,6-dibromohexane (X) by means of NaOH in methanol gives the bis benzohydroxamic ester (XI),which is treated with HCl to afford the subituted bis hydroxylamine (XII).The reaction of (XII) with dicyandiamide (V) in ethanol yields the bis biguanide (XIII),which is finally cyclized with cyclopentanone (VII) and HCl as before.
📌 参考资料/链接：
参考文献标题:Synthesis and antiprotozoal activities of some new triazine derivatives including a new antitrypanosomal agent: SIPI-1029
文献作者:Zhang,X.P.; Shen,J.; Xin,Z.M.; Qiu,Q.P.; Zhou,W.C.
参考来源:Acta Pharm Sin 1996,31(11),823
📄 详细内容
合成路线:The reaction of benzohydroxamic acid (I) with benzyl bromide (II) by means of NaOH on ethanol gives the corresponding benzyl ester (III),which is treated with HCl yielding O-benzylhydroxylamine (IV).The reaction of (IV) with dicyaniamide (V) in ethanol affords the biguanide (VI),which is cyclized with cyclopentanone (VII) and HCl giving 1-benzyloxy-2,2-dimethyl-1,2-dihydro-1,3,5-triazine-4,6-diamine (VIII).The debenzylation of (VIII) with H2 over PtO2 in ethanol yields 1-hydroxy-2,2-dimethyl-1,2-dihydro-1,3,5-triazine-4,6-diamine (IX),which is finally condensed with 1,6-dibromohexane (X) by means of NaOH in methanol.
合成路线:The reaction of benzohydroxamic acid (I) with 1,6-dibromohexane (X) by means of NaOH in methanol gives the bis benzohydroxamic ester (XI),which is treated with HCl to afford the subituted bis hydroxylamine (XII).The reaction of (XII) with dicyandiamide (V) in ethanol yields the bis biguanide (XIII),which is finally cyclized with cyclopentanone (VII) and HCl as before.
参考文献标题:Trybizine Hydrochloride
文献作者:Zhou,W.; Zhang,X.
参考来源:Drugs Fut 1999,24(10),1084
产品链接: CAS No. 172280-69-2››