新产品编号:272613

Chemical Name: N-[6-(1H-Imidazol-4-yl)hexyl]naphthalene-2-sulfonamide
CAS No. 195052-77-8
项目整合开发状态: Biological Testing
项目研究机构: James Black Foundation (Originator)
合成路线:Lithiation of 1-(N-N-dimethylsulfamoyl)imidazole (I) followed by reaction with tert-butyldimethylsilyl chloride produced the 2-silyl protected imidazole (II).Further lithiation of (II) allowed the introduction of a bromohexyl group at position 5 upon treatment with 1,6-dibromohexane yielding (III).Bromide (III) was subsequently converted into primary amine (VI) through a Gabriel synthesis involving condensation with potassium phthalimide (IV) with concomitant desilylation,and then hydrazinolysis of the resulting alkylated phthalimide (V).Condensation of amine (VI) with naphthalene-2-sulfonyl chloride (VII) furnished sulfonamide (VIII).The sulfamoyl protecting group of (VIII) was finally removed by hydrolysis with HCl.
📌 参考资料/链接:
参考文献标题:From histamine to imidazolylalkyl-sulfonamides: The design of a novel series of histamine H3-receptor antagonists
文献作者:Tozer,M.J.; Harper,E.A.; Kalindjian,S.B.; Pether,M.J.; Shankley,N.P.; Watt,G.F.
参考来源:Bioorg Med Chem Lett 1999,9(13),1825