Caracasandiamide
Chemical Name: 3beta,4beta-Bis(3,4-dimethoxyphenyl)-N,N'-bis[4-[3-(3-methyl-2-butenyl)guanidino]butyl]cyclobutane-1alpha,2alpha-dicarboxamide
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:This compound can be obtained by two related ways:1) The solid-state photodimerization of ethyl 3,4-dimethoxycinnamate (I) gives the corresponding dimeric cyclobutane (II),which is hydrolyzed with KOH in methanol yielding the corresponding diacid (III).The reaction of (III) with 4-[N2,N3-bis(tert-butoxycarbonyl)-N3-(3-methyl-2-butenyl)guanidino]butylamine (IV) by means of CMC and Ts-OMe affords the protected diamide (V),which is finally deprotected with methanesulfonic acid.2) The solid-state photodimerization of benzyl 3,4-dimethoxycinnamate (VI) gives the corresponding dimeric cyclobutane (VII),which is debenzylated by hydrogenation with H2 over Pd/C yielding the previously described diacid (III).
📌 参考资料/链接:
参考文献标题:Novel hypotensive agents from Verbesina caracasana.6.Synthesis and pharmacology of caracasandiamide
文献作者:Carmignani,M.; Volpe,A.R.; Delle Monache,F.; Botta,B.; Espinal,R.; De Bonnevaux,S.C.; De Luca,C.; Botta,M.; Corelli,F.; Tafi,A.; Ripanti,G.; Monache,G.D.
参考来源:J Med Chem 1999,42(16),3116