Nosantine, NPT-15392
诺次黄嘌呤Chemical Name: erythro-9-(2-Hydroxy-3-nonyl)hypoxanthine; erythro-9-(2-Hydroxy-3-nonyl)-1,9-dihydro-6H-purin-6-one; (R*,S*)-1,9-Dihydro-9-[1-(1-hydroxyethyl)heptyl]-6H-purin-6-one
CAS No. 76600-30-1
项目整合开发状态: Phase III
项目研究机构: Newport Pharmaceuticals (Originator), Delalande (Licensee), M.R. Leclerc (Licensee), Mitsubishi Chemical (Licensee), Sigma-Tau (Licensee)
合成路线:This compound can be obtained by two related ways:1) The condensation of 2-aminooctanoic acid (I) with acetic anhydride in pyridine at 100 C gives 3-acetamidononan-2-one (III),which is hydrolyzed with refluxing aqueous concentrated HCl yielding 3-aminononan-2-one hydrochloride (IV).The reduction of (IV) with NaBH4 in methanol affords 3-amino-2-nonanol (V),which is condensed with 4,6-dichloro-5-aminopyrimidine (VI) by means of tributylamine in refluxing pentanol giving 5-amino-6-(2-hydroxy-3-nonylamino)-4-chloropyrimidine (VII).The cyclization of (VII) with ethyl orthoformate (A) by means of ethanesulfonic acid in refluxing CHCl3 affords 9-(2-hydroxy-3-nonyl)-6-chloropurine (VIII),which is finally hydrolyzed with refluxing aqueous 0.5 N NaOH.2) The chloropurine (VIII) is treated with methanolic NH3 at 80-100 C in a pressure vessel to give 9-(2-hydroxy-3-nonyl)adenine (IX),which is then treated with NaNO2 in acetic acid aqueous HCl.
📌 参考资料/链接：
参考文献标题:9-(Hydroxy alkyl)purines
文献作者:Giner-Sorolla,A.(Newport Pharmaceuticals International Inc.; Sloan-Kettering Institute)
参考来源:US 4221910
📄 详细内容
合成路线:This compound can be obtained by two related ways:1) The condensation of 2-aminooctanoic acid (I) with acetic anhydride in pyridine at 100 C gives 3-acetamidononan-2-one (III),which is hydrolyzed with refluxing aqueous concentrated HCl yielding 3-aminononan-2-one hydrochloride (IV).The reduction of (IV) with NaBH4 in methanol affords 3-amino-2-nonanol (V),which is condensed with 4,6-dichloro-5-aminopyrimidine (VI) by means of tributylamine in refluxing pentanol giving 5-amino-6-(2-hydroxy-3-nonylamino)-4-chloropyrimidine (VII).The cyclization of (VII) with ethyl orthoformate (A) by means of ethanesulfonic acid in refluxing CHCl3 affords 9-(2-hydroxy-3-nonyl)-6-chloropurine (VIII),which is finally hydrolyzed with refluxing aqueous 0.5 N NaOH.2) The chloropurine (VIII) is treated with methanolic NH3 at 80-100 C in a pressure vessel to give 9-(2-hydroxy-3-nonyl)adenine (IX),which is then treated with NaNO2 in acetic acid aqueous HCl.
参考文献标题:Method of imparting immunomodulating and antiviral activity
文献作者:Simon,L.N.; Hadden,J.W.(Newport Pharmaceuticals International Inc.; Sloan-Kettering Institute)
参考来源:US 4221794
合成路线:This compound can be obtained by two related ways:1) The condensation of 2-aminooctanoic acid (I) with acetic anhydride in pyridine at 100 C gives 3-acetamidononan-2-one (III),which is hydrolyzed with refluxing aqueous concentrated HCl yielding 3-aminononan-2-one hydrochloride (IV).The reduction of (IV) with NaBH4 in methanol affords 3-amino-2-nonanol (V),which is condensed with 4,6-dichloro-5-aminopyrimidine (VI) by means of tributylamine in refluxing pentanol giving 5-amino-6-(2-hydroxy-3-nonylamino)-4-chloropyrimidine (VII).The cyclization of (VII) with ethyl orthoformate (A) by means of ethanesulfonic acid in refluxing CHCl3 affords 9-(2-hydroxy-3-nonyl)-6-chloropurine (VIII),which is finally hydrolyzed with refluxing aqueous 0.5 N NaOH.2) The chloropurine (VIII) is treated with methanolic NH3 at 80-100 C in a pressure vessel to give 9-(2-hydroxy-3-nonyl)adenine (IX),which is then treated with NaNO2 in acetic acid aqueous HCl.
参考文献标题:NPT-15,392
文献作者:Serradell,M.N.; Blancafort,P.; Castar,J.; Arrigoni-Martelli,E.
参考来源:Drugs Fut 1983,8(5),420
产品链接: CAS No. 76600-30-1››