Caracasanamide
Chemical Name: 3-(3,4-Dimethoxyphenyl)-N-[4-[3-(3-methyl-2-butenyl)guanidino]butyl]propenamide
项目整合开发状态: Biological Testing
项目研究机构: Consiglio Nazionale delle Ricerche (Originator)
合成路线:The reaction of S-methylisothiourea (I) with Boc2O by means of NaHCO3 gives the N-Boc protected isothiourea (II),which is condensed with 1,4-butanediamine (III) in hot THF to yield the guanidine derivative (IV).The acylation of the amino group of (IV) with 3,4-dimethoxycinnamoyl chloride (V) with THF/DMF affords the corresponding amide (VI),which is deprotected with TFA to provide N-(4-guanidinobutyl)-3,4-dimethoxycinnamamide (VII).Finally,the guanidino group of (VII) is alkylated with 3-methyl-2-butenyl bromide (VIII) catalyzed by DMAP in THF to provide the target,caracasanamide.
📌 参考资料/链接：
参考文献标题:Guanidine derivs.having hypotensive activity,compsn.containing them,and process for obtaining them
文献作者:Delle Monache,G.; Delle Monache,F.; Botta,B.; Bonnevaux Castillo,S.; Espinal,R.; De Luca,C.; Carmignani,M.(Consiglio Nazionale delle Ricerche)
参考来源:EP 0330629; JP 1990003661; US 5059624
📄 详细内容
合成路线:The condensation of 3,4-dimethoxy-N-(4-aminobutyl)cinnamamide (I) with N,N'-bis(tert-butoxycarbonyl)-S-methyl-N-(3-methyl-2-butenyl)isothiourea (II) gives the protected target compound (III),which is finally deprotected by treatment with methanesulfonic acid.
参考文献标题:Caracasanamide,a novel hypotensive agent from verbesina caracasana
文献作者:Delle Monache,G.; et al.
参考来源:Bioorg Med Chem Lett 1992,2(5),415