• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】41161

【品名】3-cyano-N-(4,4'-dinitro[1,1'-biphenyl]-2-yl)benzamide

【CA登记号】

【 分 子 式 】C20H12N4O5

【 分 子 量 】388.33924

【元素组成】C 61.86% H 3.11% N 14.43% O 20.6%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

Acylation of amino derivative (I) with 3-cyanobenzoyl chloride (II) provides amide (III) which is then cyclized to give phenanthridine (IV) by refluxing with phosphoryl chloride in nitrobenzene and catalysis of SnCl4. Hydrolysis of the nitrile derivative (IV) in H2SO4 gives carboxylic acid derivative (V). Quaternization of (V) is carried out using dimethyl sulfate and after refluxing in a HCl solution, derivative (VI) is obtained. Reduction of (VI) using iron powder in a mixture of HCl-ethanol yields the ethidium chloride derivative (VII) which is coupled to the protected arginine-linking chain (VIII) (see below) in presence of DCC and HOBt. Last step is the deprotection of the arginine moiety with TFA and separation of the obtained products.

1 Guedj, R.; Peytou, V.; Aubertin, A.-M.; Terreux, R.; Bailly, C.; Patino, N.; Condom, R.; Cabrol-Bass, D.; Gelus, N.; Synthesis and antiviral activity of ethidium - Arginine conjugates directed against the TAR RNA of HIV-1. J Med Chem 1999, 42, 20, 4042.
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) 41160 4,4'-dinitro[1,1'-biphenyl]-2-amine; 4,4'-dinitro[1,1'-biphenyl]-2-ylamine C12H9N3O4 详情 详情
(II) 34921 3-cyanobenzoyl chloride 1711-11-1 C8H4ClNO 详情 详情
(III) 41161 3-cyano-N-(4,4'-dinitro[1,1'-biphenyl]-2-yl)benzamide C20H12N4O5 详情 详情
(IV) 41162 3-(3,8-dinitro-6-phenanthridinyl)benzonitrile C20H10N4O4 详情 详情
(V) 41163 3-(3,8-dinitro-6-phenanthridinyl)benzoic acid C20H11N3O6 详情 详情
(VI) 41164 6-(3-carboxyphenyl)-5-methyl-3,8-dinitrophenanthridinium chloride C21H14ClN3O6 详情 详情
(VII) 41165 3,8-diamino-6-(3-carboxyphenyl)-5-methylphenanthridinium chloride C21H18ClN3O2 详情 详情
(VIII) 41166 methyl (2S)-2-([3-[(6-aminohexanoyl)amino]propanoyl]amino)-5-[(imino[[(2,2,5,7,8-pentamethyl-3,4,4a,8a-tetrahydro-2H-chromen-6-yl)sulfonyl]amino]methyl)amino]pentanoate C30H52N6O7S 详情 详情
Extended Information