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【结 构 式】 
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【药物名称】 【化学名称】N,N-Dimethyl-N-[2-(6-nitro-2-oxo-3,7-dihydro[1,2,6]thiadiazino[3,4,5-kl]acridin-3-yl)ethyl]amine maleate 【CA登记号】 【 分 子 式 】C21H21N5O7S 【 分 子 量 】487.49482 |
【开发单位】Medical University of Gdansk (Originator), Politechnika Gdanska (Originator), Università degli Studi di Camerino (Originator) 【药理作用】ONCOLYTIC DRUGS, DNA-Intercalating Drugs |
合成路线1
1-Chloro-4-nitro-9,10-dihydroacridin-9-one (I) is refluxed with POCl3 in the presence of a catalytic amount of DMF and subsequently reacted with ammonium carbonate in hot phenol to provide the amino acridine (II). Displacement of the 4-chloro group of (II) with N,N-dimethylethanediamine (III) in DMF at 100 C leads to amine (IV). Cyclization of (IV) with SOCl2 yields the target thiadiazinoacridine, which is finally isolated as the corresponding maleate salt.
| 【1】 Antonini, I.; Polucci, P.; Magnano, A.; Cacciamani, D.; Konieczny, M.T.; Paradziej-Lukowicz, J.; Martelli, S.; Rational design, synthesis and biological evaluation of thiadiazinoacridines: A new class of antitumor agents. Bioorg Med Chem 2003, 11, 3, 399. |
| 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) | 52276 | 1-chloro-4-nitro-9(10H)-acridinone | C13H7ClN2O3 | 详情 | 详情 | |
| (II) | 63194 | 1-chloro-4-nitro-9-acridinamine; 1-chloro-4-nitro-9-acridinylamine | C13H8ClN3O2 | 详情 | 详情 | |
| (III) | 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 |
| (IV) | 63195 | N-[2-(dimethylamino)ethyl]-N-(9-imino-4-nitro-9,10-dihydro-1-acridinyl)amine; N~1~-(9-imino-4-nitro-9,10-dihydro-1-acridinyl)-N~2~,N~2~-dimethyl-1,2-ethanediamine | C17H19N5O2 | 详情 | 详情 |