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【结 构 式】

【药物名称】

【化学名称】4-(Cyano-NNO-azoxy)-N-[6-[N2-cyano-N3-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]guanidino]hexyl]benzamide

【CA登记号】

【 分 子 式 】C31H41N9O3

【 分 子 量 】587.73092

【开发单位】Università degli Studi "La Sapienza" (Originator), Università degli Studi di Milano (Originator), Università degli Studi di Torino (Originator), Università degli Studi Piemonte Orient. (Originator)

【药理作用】Anti-Helicobacter Pylori Agents, Antiulcer Drugs, Gastric Antisecretory Drugs, GASTROINTESTINAL DRUGS, Histamine H2 Receptor Antagonists

合成路线1

Condensation of amine (I) with diphenyl cyanocarbonimidate (II) affords isourea (III), which is then converted into cyanoguanidine (V) by coupling with diamine (IV) in CH2Cl2. The final step for the synthesis of the desired product is the reaction of the primary amine group of (V) with the active ester (VI) obtained by activation of calvatic acid (VII) with N-hydroxysuccinimide (N-HOSu) and N,N'-dicyclohexyl-carbodiimide (DCC) in THF.

1 Hirschfeld, J.; et al.; Iodoaminopotentidine and related compounds: A new class of ligands with high affinity and selectivity for the histamine H2 receptor. J Med Chem 1992, 35, 12, 2231.
2 Sorba, G.; Dubini, F.; Brenciaglia, M.I.; Bertinaria, M.; Scaltrito, M.M.; Di Stilo, A.; Gasco, A.; Anti-Helicobacter pylori agents endowed with H2-antagonist properties. Bioorg Med Chem Lett 2001, 11, 3, 403.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 16105 3-[3-(piperidinomethyl)phenoxy]-1-propanamine; 3-[3-(piperidinomethyl)phenoxy]propylamine C15H24N2O 详情 详情
(II) 25868 1-[(cyanoimino)(phenoxy)methoxy]benzene 107-37-9 C14H10N2O2 详情 详情
(III) 48290 1-[3-(3-[[(cyanoimino)(phenoxy)methyl]amino]propoxy)benzyl]piperidine C23H28N4O2 详情 详情
(IV) 22344 1,6-hexanediamine; 6-aminohexylamine 124-09-4 C6H16N2 详情 详情
(V) 48291 N-(6-aminohexyl)-N''-cyano-N'-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]guanidine C23H38N6O 详情 详情
(VI) 48292 2-cyano-1-(4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]phenyl)-1-oxidodiazen-1-ium C12H8N4O5 详情 详情
(VII) 48293 (E)-1-(4-carboxyphenyl)-2-cyano-1-oxidodiazen-1-ium C8H5N3O3 详情 详情
Extended Information