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【结 构 式】 
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【药物名称】HI-281 【化学名称】6-(3,5-Dimethylbenzyl)-5-isopropyl-2-(methylsulfanylmethylsulfanyl)-4(3H)-pyrimidinone 【CA登记号】210645-96-8 【 分 子 式 】C18H24N2OS2 【 分 子 量 】348.53278 |
【开发单位】Parker Hughes Institute (Originator) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Contraceptives, Disorders of Sexual Function and Reproduction, Treatment of, ENDOCRINE DRUGS, Female Contraceptives, Vaginal Spermicides, Reverse Transcriptase Inhibitors |
合成路线1
The condensation of 2-(3,5-dimethylphenyl)acetonitrile (I) with ethyl 2-bromo-3-methylbutyrate (II) by means of Zn in THF gives the beta-ketoester (III), which is cyclized with thiourea (IV) by means of sodium ethoxide in ethanol yielding the thioxopyrimidinone (V). Finally, this compound is condensed with choromethyl methyl sulfide by means of K2CO3 in DMF.
| 【1】 Vig, R.; Mao, C.; Venkatachalam, T.K.; Tuel-Ahlgren, L.; Sudbeck, E.A.; Uckun, F.M.; 5-Alkyl-2-[(methylthiomethyl)thio]-6-(benzyl)-pyrimidin-4-(1H)-ones as potent non-nucleoside reverse transcriptase inhibitors of S-DABO series. Bioorg Med Chem Lett 1998, 8, 12, 1461. |
| 【2】 Sudbeck, E.A.; Mao, C.; Vig, R.; Venkatachalam, T.K.; Tuel-Ahlgren, L.; Uckun, F.M.; Structure-based design of novel dihydroalkoxybenzyloxopyrimidine derivatives as potent nonnucleoside inhibitors of the human immunodeficiency virus reverse transcriptase. Antimicrob Agents Chemother 1998, 42, 12, 3225. |
| 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) | 30213 | 2-(3,5-dimethylphenyl)acetonitrile | 39101-54-7 | C10H11N | 详情 | 详情 |
| (II) | 27032 | 2-Bromoisovalerianic acid ethyl ester; ethyl 2-bromo-3-methylbutanoate | 609-12-1 | C7H13BrO2 | 详情 | 详情 |
| (III) | 30214 | ethyl 4-(3,5-dimethylphenyl)-2-isopropyl-3-oxobutanoate | C17H24O3 | 详情 | 详情 | |
| (IV) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
| (V) | 30215 | 6-(3,5-dimethylbenzyl)-5-isopropyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone | C16H20N2OS | 详情 | 详情 | |
| (VI) | 27701 | chloro(methylsulfanyl)methane | 2373-51-5 | C2H5ClS | 详情 | 详情 |