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【结 构 式】 
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【药物名称】 【化学名称】3,5-Dichloro-2-(3,5-dichloro-2-hydroxyphenylsulfonamido)-N-[4-(6-ethoxybenzothiazol-2-ylsulfanyl)phenyl]benzamide 【CA登记号】 【 分 子 式 】C28H19Cl4N3O5S3 【 分 子 量 】715.48473 |
【开发单位】Bayer (Originator) 【药理作用】Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, ONCOLYTIC DRUGS, Cathepsin D Inhibitors |
合成路线1
The condensation of mercapto benzothiazole (I) with 4-fluoronitrobenzene (II) afforded the 4-nitrophenyl thioether (III). After reduction of the nitro group of (III) with iron in HOAc, the resulting aniline (IV) was acylated with the dichloroisatoic anhydride (V) to produce the anthranylamide (VI). This was finally condensed with 3,5-dichloro-2-hydroxybenzenesulfonyl chloride (VII) to yield the corresponding sulfonamide.
| 【1】 Dumas, J.; Witowsky, J.; Hatoum-Mokdad, H.; Sibley, R.; Chen, J.; Dixon, B.; Wong, S.; Konig, G.; Britelli, D.; Synthesis and structure activity relationships of novel small molecule cathepsin D inhibitors. Bioorg Med Chem Lett 1999, 9, 17, 2531. |
| 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) | 34296 | 6-ethoxy-1,3-benzothiazol-2-ylhydrosulfide; 6-ethoxy-1,3-benzothiazole-2-thiol | 120-53-6 | C9H9NOS2 | 详情 | 详情 |
| (II) | 14153 | 4-Fluoronitrobenzene; 1-Fluoro-4-nitrobenzene | 350-46-9 | C6H4FNO2 | 详情 | 详情 |
| (III) | 46843 | 6-ethoxy-2-[(4-nitrophenyl)sulfanyl]-1,3-benzothiazole; ethyl 2-[(4-nitrophenyl)sulfanyl]-1,3-benzothiazol-6-yl ether | C15H12N2O3S2 | 详情 | 详情 | |
| (IV) | 46844 | 4-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]aniline; 4-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]phenylamine | C15H14N2OS2 | 详情 | 详情 | |
| (V) | 46845 | 3,5-Dichloroisatoic anhydride; 6,8-dichloro-2H-3,1-benzoxazine-2,4(1H)-dione | 4693-00-9 | C8H3Cl2NO3 | 详情 | 详情 |
| (VI) | 46846 | 2-amino-3,5-dichloro-N-[4-[(6-ethoxy-1,3-benzothiazol-2-yl)sulfanyl]phenyl]benzamide | C22H17Cl2N3O2S2 | 详情 | 详情 | |
| (VII) | 46847 | 3,5-dichloro-2-hydroxybenzenesulfonyl chloride | 23378-88-3 | C6H3Cl3O3S | 详情 | 详情 |
Extended Information