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【结 构 式】 
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【药物名称】Tomeglovir, BAY-38-4766 【化学名称】N-[4-[5-(Dimethylamino)-1-naphthylsulfonamido]phenyl]-3-hydroxy-2,2-dimethylpropionamide 【CA登记号】233254-24-5 【 分 子 式 】C23H27N3O4S 【 分 子 量 】441.55334 |
【开发单位】Bayer (Originator) 【药理作用】Anti-Cytomegalovirus Drugs, ANTIINFECTIVE THERAPY, Antiviral Drugs |
合成路线1
The reaction of 5-(dimethylamino)naphthalene-1-sulfonyl chloride (I) with 4-nitroaniline (II) in pyridine gives the corresponding sulfonamide (III), which is reduced at the nitro group with hydrogen over Pd/C in ethanol, yielding the expected amine (IV). Finally, this compound is condensed with 3-hydroxy-2,2-dimethylpropionic acid (V) by means of propylphosphonic anhydride (PRPA) and triethylamine in dichloromethane/ethyl acetate.
| 【1】 Hallenberger, S.; Weber, O.; Bender, W.; Eckenberg, P.; Reefschlaeger, J.; Goldmann, S.; Trappe, J.; Haerter, M.; A novel nonnucleosidic inhibitor of human cytomegalovirus replication. Intersci Conf Antimicrob Agents Chemother 1999, Abst F940. |
| 【2】 Leeson, P.A.; Sorbera, L.A.; Castañer, J.; Bay-38-4766. Drugs Fut 1999, 24, 12, 1297. |
| 【3】 Trappe, J.; Weber, O.; Eckenberg, P.; Hallenberger, S.; Bender, W.; Goldmann, S.; Harter, M.; Reefschlager, J. (Bayer AG); Novel naphthyl-substd. and anilide-substd. sulfonamides. WO 9937609 . |
| 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) | 19027 | 5-(dimethylamino)-1-naphthalenesulfonyl chloride | 605-65-2 | C12H12ClNO2S | 详情 | 详情 |
| (II) | 15547 | 4-nitrophenylamine; p-Nitroaniline; 4-nitroaniline | 100-01-6 | C6H6N2O2 | 详情 | 详情 |
| (III) | 30616 | 5-(dimethylamino)-N-(4-nitrophenyl)-1-naphthalenesulfonamide | C18H17N3O4S | 详情 | 详情 | |
| (IV) | 30617 | N-(4-aminophenyl)-5-(dimethylamino)-1-naphthalenesulfonamide | C18H19N3O2S | 详情 | 详情 | |
| (V) | 30618 | 3-hydroxy-2,2-dimethylpropionic acid | 4835-90-9 | C5H10O3 | 详情 | 详情 |
Extended Information