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【结 构 式】

【药物名称】SN-22977, NSC-683247, AMAC

【化学名称】9-Amino-N-[2-(dimethylamino)ethyl]-5-methylacridine-4-carboxamide

【CA登记号】

【 分 子 式 】C19H22N4O

【 分 子 量 】322.41339

【开发单位】University of Auckland (Originator)

【药理作用】ONCOLYTIC DRUGS, DNA-Intercalating Drugs

合成路线1

The intermediate 6-methyldiphenylamine-2,2'-dicarboxylic acid (V) has been synthesized in two similar ways. 1. By Jourdan-Ullman copper-catalyzed condensation of 6-methylbenzoic acid (I) with 2-aminobenzoic acid (II); and 2. By the same type of condensation, but using 2-amino-3-methylbenzoic acid (III) and 2-chlorobenzoic acid (IV). The cyclization of the intermediate dicarboxylic acid (V) under acidic conditions gives 5-methyl-9-oxo-9,10-dihydroacridine-4-carboxylic acid (VI), which is treated with hot SOCl2 and DMF to yield 9-choloro-5-methylacridine-4-carbonyl chloride (VII). The reaction of (VII) with N,N-dimethylethylenediamine (VIII) in dichloromethane affords the corresponding amide (IX), which is finally treated first with phenol at 100 C and then with a stream of dry ammonia at 110-20 C to obtain the target 9-aminoacridine derivative.

1 Rewcastle, G.W.; et al.; Potential antitumor agents. 46. Structure-activity relationships for acridine monosubstituted derivatives of the antitumor agent N-[2-(dimethylamino)ethyl]-9-aminoacridine-4-carboxamide. J Med Chem 1986, 29, 4, 472.
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) 51949 2-Chloro-3-methylbenzoic acid 15068-35-6 C8H7ClO2 详情 详情
(II) 11661 2-Aminobenzoic acid;Anthranilic acid; o-Aminobenzoic acid 118-92-3 C7H7NO2 详情 详情
(III) 48130 2-amino-3-methylbenzoic acid 4389-45-1 C8H9NO2 详情 详情
(IV) 10203 o-Chlorobenzoic acid; 2-Chlorobenzoic acid 118-91-2 C7H5ClO2 详情 详情
(V) 51950 2-(2-carboxyanilino)-3-methylbenzoic acid C15H13NO4 详情 详情
(VI) 30493 5-methyl-9-oxo-9,10-dihydro-4-acridinecarboxylic acid C15H11NO3 详情 详情
(VII) 30494 9-chloro-5-methyl-4-acridinecarbonyl chloride C15H9Cl2NO 详情 详情
(VIII) 14481 (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carbothioic S-acid C21H26F2O4S 详情 详情
(IX) 51951 9-chloro-N-[2-(dimethylamino)ethyl]-5-methyl-4-acridinecarboxamide C19H20ClN3O 详情 详情
Extended Information