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【结 构 式】 
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【药物名称】Amsacrine, CI-880, NSC-141549(HCl), SN-11841, NSC-249992, NSC-156303, m-AMSA, Amsidyl, Amecrin, Amsidine 【化学名称】4'-(9-Acridinylamino)methanesulfon-m-anisidine 【CA登记号】51264-14-3, 54301-15-4 (HCl), 54301-16-5 (monomethanesulfonate) 【 分 子 式 】C21H19N3O3S 【 分 子 量 】393.46788 |
【开发单位】Bristol-Myers Squibb (Originator), Pfizer (Originator) 【药理作用】ONCOLYTIC DRUGS, DNA-Intercalating Drugs |
合成路线1
The reaction of 4-nitro-m-anisidine (I) with methanesulfonyl chloride in pyridine gives 4-nitromethanesulfony-m-anisidine (II), which is reduced with Fe and aqueous HCl yielding 4-aminomethanesulfony-m-anisidine (III) . Finally, this compound is condensed with 9-chloroacridine (IV).
| 【1】 Denny, W.A.; et al.; Potential antitumor agents. 26. Anionic congeners of the 9-anilinoacridine. J Med Chem 1977, 21, 1, 5-10. |
| 【2】 Cain, B.F.; et al.; Potential antitumor agents. 16. 4-(Acridin-9-ylamino)methanesulfonanilides. J Med Chem 1975, 18, 11, 1110-17. |
| 【3】 Cain, B.F.; et al.; Potential antitumor agents. 23. 4'-(9-Acridinylamino)alkanesulfonanilide congeners bearing hydrophilic functionality. J Med Chem 1977, 20, 8, 987-996. |
| 【4】 Paton, D.M.; Blancafort, P.; Serradell, M.N.; Castaner, J.; m-AMSA. Drugs Fut 1980, 5, 6, 277. |
| 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) | 32670 | 3-methoxy-4-nitroaniline; 3-methoxy-4-nitrophenylamine | C7H8N2O3 | 详情 | 详情 | |
| (II) | 32671 | N-(3-methoxy-4-nitrophenyl)methanesulfonamide | C8H10N2O5S | 详情 | 详情 | |
| (III) | 30496 | N-(4-amino-3-methoxyphenyl)methanesulfonamide | C8H12N2O3S | 详情 | 详情 | |
| (IV) | 32672 | 9-chloroacridine | 1207-69-8 | C13H8ClN | 详情 | 详情 |
Extended Information