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【结 构 式】

【药物名称】WMC-79

【化学名称】5-Nitro-2-[3-[4-[3-(6-oxo-6H-imidazo[4,5,1-de]acridin-5-ylamino)propyl]piperazin-1-yl]propyl]benzo[de]isoquinoline-1,3(2H)-dione

【CA登记号】359630-61-8

【 分 子 式 】C36H33N7O5

【 分 子 量 】643.70831

【开发单位】National Cancer Institute (Originator)

【药理作用】Colorectal Cancer Therapy, Oncolytic Drugs, Pancreatic Cancer Therapy, Apoptosis Inducers, DNA-Intercalating Drugs

合成路线1

2,6-Dichloro-3-nitrobenzoic acid (I) was condensed with aniline (II) to produce the anilinobenzoic acid (III), which was subsequently cyclized to the acridinone (IV) upon treatment with POCl3. Displacement of the chloride group of (IV) with 1,4-bis(3-aminopropyl)piperazine (V) in DMF afforded adduct (VI). The nitro group of (VI) was reduced by catalytic hydrogenation in the presence of Raney-Ni and formic acid, and the intermediate formamide was further cyclized under acidic conditions to the imidazoacridinone (VII). Finally, conversion of the primary amino group of (VII) to the target imide was achieved by heating with 3-nitro-1,8-naphthalenedicarboxylic anhydride (VIII) in DMF.

1 Cholody, W.M.; Michejda, C.J.; Kosakowska-Cholody, T. (US Department of Health & Human Services); 1,8-Naphthalimide imidazo[4,5,1-de]acridones with anti-tumor activity. WO 0166545 .
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) 52274 2,5-Dichloro-3-nitrobenzoic acid 88-86-8 C7H3Cl2NO4 详情 详情
(II) 12294 Aniline; Phenylamine 62-53-3 C6H7N 详情 详情
(III) 52275 6-chloro-3-nitro-2-(phenylamino)benzoic acid C13H9ClN2O4 详情 详情
(IV) 52276 1-chloro-4-nitro-9(10H)-acridinone C13H7ClN2O3 详情 详情
(V) 52277 1,4-Bis(3-aminopropyl)piperazine; N,N'-Bis(3-Aminopropyl)piperazine; Bis aminopropyl piperazine; 1,4-Di(3-aminopropyl)piperazine 7209-38-3 C10H24N4 详情 详情
(VI) 52278 1-({3-[4-(3-aminopropyl)-1-piperazinyl]propyl}amino)-4-nitro-9(10H)-acridinone C23H30N6O3 详情 详情
(VII) 52279 5-({3-[4-(3-aminopropyl)-1-piperazinyl]propyl}amino)-6H-imidazo[4,5,1-de]acridin-6-one C24H30N6O 详情 详情
(VIII) 15864 5-nitro-1H,3H-benzo[de]isochromene-1,3-dione; 3-Nitro-1,8-naphthalic anhydride 3027-38-1 C12H5NO5 详情 详情
Extended Information