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【结 构 式】

【药物名称】

【化学名称】N,2-Bis[2-(dimethylamino)ethyl]-9-nitro-2,6-dihydropyrazolo[3,4,5-kl]acridine-5-carboxamide dihydrochloride

【CA登记号】220249-88-7

【 分 子 式 】C22H29Cl2N7O3

【 分 子 量 】510.42753

【开发单位】Università degli Studi di Camerino (Originator)

【药理作用】Oncolytic Drugs, DNA-Intercalating Drugs

合成路线1

The Ullmann condensation between 2-chloro-5-nitrobenzoic acid (I) and 2-amino-4-chlorobenzoic acid (II) afforded the diaryl amine (III). Cyclization of (III) by treatment with POCl3 in refluxing xylene yielded a mixture of the desired acridine (IV) and minor amounts of its regioisomer (V). The isomeric mixture of acids (IV) and (V) was activated as the respective mixed anhydrides with ethyl chloroformate and subsequently condensed with N,N-dimethylethylenediamine (VI) to produce the corresponding amides. The required isomer (VII) was easily isolated from the mixture owing to its insolubility in the reaction solvent. Finally, the title pyrazoloacridine compound was prepared by condensation of (VII) with 2-(dimethylamino)ethyl hydrazine in 2-ethoxyethanol at 120 C.

1 Antonini, I.; et al.; Synthesis, antitumor cytotoxicity, and DNA-binding of novel N-5,2-Di(omega-aminoalkyl)-2,6-dihydropyrazolo[3,4,5-kl) acridine-5-carboxamides. J Med Chem 2001, 44, 20, 3329.
2 Matelli, S.; Polucci, P.; Antonini, I. (Università degli Studi di Camerino); Pyrazolo-acridine derivs. having antitumour activity. WO 9906405 .
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) 10188 2-Chloro-5-nitrobenzoic acid 2516-96-3 C7H4ClNO4 详情 详情
(II) 52504 4-Chloro-2-aminobenzoic acid; 2-Amino-4-chlorobenzoic acid; 2-Carboxy-5-chloroaniline; 3-Amino-4-carboxy-1-chlorobenzene; 4-Chloroanthranilic acid 89-77-0 C7H6ClNO2 详情 详情
(III) 52505   C14H9ClN2O6 详情 详情
(IV) 52506 1-chloro-7-nitro-9-oxo-9,10-dihydro-4-acridinecarboxylic acid C14H7ClN2O5 详情 详情
(V) 52507 6-chloro-2-nitro-9-oxo-9,10-dihydro-4-acridinecarboxylic acid C14H7ClN2O5 详情 详情
(VI) 14881 N-(2-aminoethyl)-N,N-dimethylamine; N(1),N(1)-dimethyl-1,2-ethanediamine; 2-Dimethylaminoethylamine 108-00-9 C4H12N2 详情 详情
(VII) 52508 1-chloro-N-[2-(dimethylamino)ethyl]-7-nitro-9-oxo-9,10-dihydro-4-acridinecarboxamide C18H17ClN4O4 详情 详情
(VIII) 41186 N-(2-hydrazinoethyl)-N,N-dimethylamine; 2-hydrazino-N,N-dimethyl-1-ethanamine C4H13N3 详情 详情
Extended Information