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【结 构 式】 
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【分子编号】30497 【品名】9-[2-methoxy-4-[(methylsulfonyl)amino]anilino]-4-methyl-5-[(methylamino)carbonyl]acridinium chloride 【CA登记号】 |
【 分 子 式 】C24H25ClN4O4S 【 分 子 量 】501.00576 【元素组成】C 57.54% H 5.03% Cl 7.08% N 11.18% O 12.77% S 6.4% |
合成路线1
该中间体在本合成路线中的序号：(VIII)2-Iodoisophthalic acid (II) is reacted with o-toluidine (I) to give 2-N-(2-methylphenyl)aminoisophthalic acid (III). Cyclization with concentrated H2SO4 provides the 5-methyl-9-oxoacridan-4-carboxylic acid (IV). Conversion of this compound to 5-methyl-9-chloroacridine-4-carbonyl chloride (V) and subsequent selective reaction first with methylamine to provide the methylcarboxamide (VI) and secondly with 4-amino-3-methoxymethanesulfonanilide (VII) gives the hydrochloride salt (VIII) of the desired compound. Conversion via the free base to the isethionate salt provides CI-921.
| 【1】 Baguley, B.C.; Denny, W.A.; Finlay, G.J.; Wilson, W.R.; Twigden, S.J.; Atwell, G.J.; Rewcastle, G.W.; Synthesis and antitumour activity and DNA binding properties of a new derivative of amsacrine N,5-dimethyl-9-[(2-methoxy-4-methylsulfonylamino)phenylamino]-4-acridine carboxamide. Cancer Res 1984. |
| 【2】 Denny, W.A.; Baguley, B.C.; Atwell, G.J.; Potential antitumor agents. 40. Orally active 4,5-disubstituted derivatives of amsacrine. J Med Chem 1984, 27, 3, 363-366. |
| 【3】 Denny, W.A.; Atwell, G.J.; Baguley, B.C.; CI-921. Drugs Fut 1984, 9, 8, 575. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 13359 | 2-Hydroxy-1-ethanesulfonic acid | 107-36-8 | C2H6O4S | 详情 | 详情 | |
| (I) | 15511 | o-toluidine; 2-methylphenylamine;2-Methylaniline；2-Aminotoluene;1-Amino-2-methylbenzene;1-Methyl-2-aminobenzene; ortho-Toluidine | 95-53-4 | C7H9N | 详情 | 详情 |
| (II) | 30491 | 2-Iodoisophthalic acid | C8H5IO4 | 详情 | 详情 | |
| (III) | 30492 | 2-(2-toluidino)isophthalic acid | C15H13NO4 | 详情 | 详情 | |
| (IV) | 30493 | 5-methyl-9-oxo-9,10-dihydro-4-acridinecarboxylic acid | C15H11NO3 | 详情 | 详情 | |
| (V) | 30494 | 9-chloro-5-methyl-4-acridinecarbonyl chloride | C15H9Cl2NO | 详情 | 详情 | |
| (VI) | 30495 | 9-chloro-N,5-dimethyl-4-acridinecarboxamide | C16H13ClN2O | 详情 | 详情 | |
| (VII) | 30496 | N-(4-amino-3-methoxyphenyl)methanesulfonamide | C8H12N2O3S | 详情 | 详情 | |
| (VIII) | 30497 | 9-[2-methoxy-4-[(methylsulfonyl)amino]anilino]-4-methyl-5-[(methylamino)carbonyl]acridinium chloride | C24H25ClN4O4S | 详情 | 详情 |