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Guanadrel sulfate, U-28288D, CL-1388R, Hylorel

硫酸胍那决尔 胍那决尔 Chemical Name: (1,4-Dioxaspiro[4.5]dec-2-yl)guanidine sulfate
CAS No. 22195-34-2, 40580-59-4 (free base)
项目整合开发状态: Launched-1983
项目研究机构: Pfizer (Originator), Celltech (Not Determined)
合成路线: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
📌 参考资料/链接:
参考文献标题:Process for the preparation of 1,3-dioxolan-4-yl-alcoyl-guanidines and its intermediates
文献作者:Aaron,J.E.Jr.; Hardie,W.R.
参考来源:FR 1522153

📄 详细内容


合成路线: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
文献作者:Xiao,J.-H.; Durand,B.; Chambon,P.; Voorhees,J.J.
参考来源:J Biol Chem 1995,270(7),3001


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


产品链接: CAS No. 22195-34-2››

产品链接: CAS No.40580-59-4››