【药物名称】Guanadrel sulfate, U-28288D, CL-1388R, Hylorel
化学结构式(Chemical Structure):
参考文献No.60922
标题:Process for the preparation of 1,3-dioxolan-4-yl-alcoyl-guanidines and its intermediates
作者:Aaron, J.E. Jr.; Hardie, W.R.
来源:FR 1522153
合成路线图解说明:

The condensation of 2-(chloromethyl)-1,4-dioxaspiro[4,5]decane (I) with the sodium salt of phthalimide (II) in hot DMF affords the N-substituted phthalimide (III). Subsequent phthaloyl group hydrazinolysis gives the primary amine (IV). Finally, condensation of amine (IV) with S-methyl pseudothiourea sulfate (V) leads to the title guanidine derivative

参考文献No.298923
标题:Endogenous retinoic acid receptor (RAR)-retinoid X receptor (RXR) heterodimers are the major functional forms regulating retinoid-responsive elements in adult human keratinocytes. Binding of ligands to RAR only is sufficient for RAR.RXR heterodimers to co
作者:Xiao, J.-H.; Durand, B.; Chambon, P.; Voorhees, J.J.
来源:J Biol Chem 1995,270(7),3001
合成路线图解说明:

In a different method, acetylation of 3-amino-1,2-propanediol (I) yields the amide diol (II). Ketalization of cyclohexanone (III) with diol (II) furnishes the spiro dioxolane (IV). The acetamide function of (IV) is then hydrolyzed to amine (V) employing aqueous hydrazine. Amine (V) is condensed with N,N'-di-(carbobenzoxy)-N''-(trifluoromethylsulfonyl)guanidine (VI) to produce the protected guanidine (VII). The N-carbobenzoxy groups of (VII) are finally removed by hydrogenolysis over Pd/C. Alternatively, amine (V) is condensed with cyanogen bromide to produce the cyanamide (VIII). Then, reaction of cyanamide (VIII) with ammonium chloride in aqueous ammonia furnishes the title guanidine compound

参考文献No.710948
标题:N-Hydroxyl derivatives of guanidine based drugs as enzymatic NO donors
作者:Xian, M.; Li, X.; Tang, X.; Chen, X.; Zheng, Z.; Galligan, J.J.; Kreulen, D.L.; Wang, P.G.
来源:Bioorg Med Chem Lett 2001,11(17),2377
合成路线图解说明:

In a different method, acetylation of 3-amino-1,2-propanediol (I) yields the amide diol (II). Ketalization of cyclohexanone (III) with diol (II) furnishes the spiro dioxolane (IV). The acetamide function of (IV) is then hydrolyzed to amine (V) employing aqueous hydrazine. Amine (V) is condensed with N,N'-di-(carbobenzoxy)-N''-(trifluoromethylsulfonyl)guanidine (VI) to produce the protected guanidine (VII). The N-carbobenzoxy groups of (VII) are finally removed by hydrogenolysis over Pd/C. Alternatively, amine (V) is condensed with cyanogen bromide to produce the cyanamide (VIII). Then, reaction of cyanamide (VIII) with ammonium chloride in aqueous ammonia furnishes the title guanidine compound

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