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【结 构 式】 
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【药物名称】Pyrazoloacridine, PZA, NSC-366140, PD-115934 【化学名称】9-Methoxy-N,N-dimethyl-5-nitro-2,6-dihydropyrazolo[3,4,5-kl]acridine-2-propanamine 【CA登记号】99009-20-8, 99009-21-9 (methanesulfonate) 【 分 子 式 】C19H21N5O3 【 分 子 量 】367.41092 |
【开发单位】Pfizer (Originator), National Cancer Institute (Codevelopment) 【药理作用】Bladder Cancer Therapy , Brain Cancer Therapy, Breast Cancer Therapy, Glioblastoma MultiformeTherapy, Melanoma Therapy, Oncolytic Drugs, Ovarian Cancer Therapy, Pancreatic Cancer Therapy, Solid Tumors Therapy, DNA Topoisomerase I Inhibitors, DNA Topoisomerase II Inhibitors, DNA-Intercalating Drugs |
合成路线1
The condensation of 4-methoxyaniline (I) with 2,6-dichloro-3-nitrobenzoic acid (II) by means of DIEA or N,N-dimethylaniline at 75 C gives 6-chloro-2-(4-methoxyphenylamino)-3-nitrobenzoic acid (III), which is cyclized in refluxing POCl3 to yield the acridone (IV). Finally, this compound is condensed with N-[3-(dimethylamino)propyl]hydrazine (V) in THF/methanol to afford the target 2,6-dihydro-pyrazolo[3,4,5-kl]acridine.
| 【1】 Capps, D.B. (Pfizer Inc.); Pyrazolo[3,4,5-kl]acridine cpds., pharmaceutical compsns. the same and processes for their production. EP 0138302; ES 8701758; ES 8703468; ES 8703874; ES 8703875; JP 1985069084; JP 1994041127; US 4555572 . |
| 【2】 Capps, D.B.; et al.; 2-(Aminoalkyl)-5-nitropyrazolo[3,4,5-kl]acridines, a new class of anticancer agents. J Med Chem 1992, 35, 26, 4770. |
| 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) | 10478 | p-Anisidine; 4-Methoxyaniline; 4-Methoxyphenylamine | 104-94-9 | C7H9NO | 详情 | 详情 |
| (II) | 52274 | 2,5-Dichloro-3-nitrobenzoic acid | 88-86-8 | C7H3Cl2NO4 | 详情 | 详情 |
| (III) | 53913 | 6-Chloro-2-(4-methoxyphenylamino)-3-nitrobenzoic acid | C14H11ClN2O5 | 详情 | 详情 | |
| (IV) | 53914 | 1-chloro-7-methoxy-4-nitro-9(10H)-acridinone | C14H9ClN2O4 | 详情 | 详情 | |
| (V) | 53915 | 3-hydrazino-N,N-dimethyl-1-propanamine; N-(3-hydrazinopropyl)-N,N-dimethylamine | C5H15N3 | 详情 | 详情 |