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【结 构 式】 
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【药物名称】 【化学名称】1-[5-[2-[N-[4-(Acetamidosulfonyl)phenyl]carbamoyl]phenylsulfanyl]-5-oxopentyl]pyridinium bromide 【CA登记号】221120-25-8 【 分 子 式 】C25H26BrN3O5S2 【 分 子 量 】592.53507 |
【开发单位】Achillion (Originator), National Institutes of Health (Originator) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY |
合成路线1
Condensation of 2,2’-dithiodibenzoyl chloride (I) with sulfacetamide (II) in pyridine afforded diamide (III). Reductive celavage of the disulfide bond of (III) by means of tris(2-carboxyethyl)phosphine produced the corresponding thiol (IV), which was subsequently acylated with 5-bromovaleryl chloride (V) yielding thioester (VI). Finally, displacement of the bromide with pyridine furnished the title pyridinium salt.
| 【1】 Turpin, J.A.; Song, Y.; Inman, J.K.; Huang, M.; Wallqvist, A.; Maynard, A.; Covell, D.G.; Rice, W.G.; Appella, E.; Synthesis and biological properties of novel pyridinioalkanoyl thiolesters (PATE) as anti-HIV-1 agents that target the viral nucleocapsid protein zinc fingers. J Med Chem 1999, 42, 1, 67. |
| 【2】 Song, Y.; Turpin, J.A.; Huang, M.; Inman, J.K.; Walqvist, A.; Appella, E.; Maynard, A.; Rice, W.G.; Covell, D.G. (US Department of Health & Human Services); Novel thiolesters and uses thereof. WO 9965871 . |
| 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) | 20405 | 2-[[2-(chlorocarbonyl)phenyl]disulfanyl]benzoyl chloride | C14H8Cl2O2S2 | 详情 | 详情 | |
| (II) | 41626 | N-acetyl-4-aminobenzenesulfonamide | 144-80-9 | C8H10N2O3S | 详情 | 详情 |
| (III) | 41627 | 2-[[2-([4-[(acetamido)sulfonyl]anilino]carbonyl)phenyl]disulfanyl]-N-[4-[(acetamido)sulfonyl]phenyl]benzamide | C30H26N4O8S4 | 详情 | 详情 | |
| (IV) | 41628 | N-[4-[(acetamido)sulfonyl]phenyl]-2-sulfanylbenzamide | n/a | C15H14N2O4S2 | 详情 | 详情 |
| (V) | 39700 | 5-bromopentanoyl chloride | 4509-90-4 | C5H8BrClO | 详情 | 详情 |
| (VI) | 41629 | S-[2-([4-[(acetamido)sulfonyl]anilino]carbonyl)phenyl] 5-bromopentanethioate | C20H21BrN2O5S2 | 详情 | 详情 |
Extended Information