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【结 构 式】

【药物名称】Zinviroxime((Z)-isomer), Enviroxime, AR-336, LY-122772

【化学名称】(E)-2-Amino-6-benzoyl-1-(isopropylsulfonyl)benzimidazole oxime

【CA登记号】72301-79-2, 72301-78-1 ((Z)-isomer), 63198-97-0 (undefined stereoch.)

【 分 子 式 】C17H18N4O3S

【 分 子 量 】358.42201

【开发单位】Lilly (Originator)

【药理作用】ANTIINFECTIVE THERAPY, Antiviral Drugs

合成路线1

The acetylation of 4-aminobenzophenone (I) with acetic anhydride in hot benzene gives 4-acetamidobenzophenone (II), which is nitrated with 90% HNO3 in acetic acid-acetic anhydride yielding 4-acetamido-3-nitrobenzophenone (III). The hydrolysis of (III) with H2SO4 affords 4-amino-3-nitrobenzophenone (IV), which is reduced with H2 over Raney-Ni in THF to give 3,4-diaminobenzophenone (V). The cyclization of (V) with cyanogen bromide in methanol-water gives rise to 2-amino-5-benzoylbenzimidazol (VI), which is treated with isopropylsulfonyl chloride (A) and NaH in dimethoxyethane affording 2-amino-1-isopropylsulfonyl-6-benzoylbenzimidazol (VII). Finally, this compound is treated with hydroxylamine hydrochloride in refluxing methanol.

1 Paget, C.J.; et al.; DE 2638551 .
2 Castaner, J.; Hopkins, S.J.; AR-336. Drugs Fut 1980, 5, 3, 120.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 18477 2-propanesulfonyl chloride 10147-37-2 C3H7ClO2S 详情 详情
(I) 39112 3-Aminobenzophenone; (3-aminophenyl)(phenyl)methanone 2835-78-1 C13H11NO 详情 详情
(II) 39113 N-(3-benzoylphenyl)acetamide 58202-86-1 C15H13NO2 详情 详情
(III) 39114 N-(5-benzoyl-2-nitrophenyl)acetamide C15H12N2O4 详情 详情
(IV) 39115 (3-amino-4-nitrophenyl)(phenyl)methanone C13H10N2O3 详情 详情
(V) 12830 (3,4-Diaminophenyl)phenylmethanone; 3,4-Diaminobenzophenone 39070-63-8 C13H12N2O 详情 详情
(VI) 39116 (2-amino-1H-benzimidazol-6-yl)(phenyl)methanone C14H11N3O 详情 详情
(VII) 39117 [2-amino-1-(isopropylsulfonyl)-1H-benzimidazol-6-yl](phenyl)methanone C17H17N3O3S 详情 详情
Extended Information