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【结 构 式】 
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【药物名称】PD-164387 【化学名称】2,6-Di-tert-butyl-4-[5-(ethylsulfanyl)-1,3,4-thiadiazol-2-yl]phenol 【CA登记号】 【 分 子 式 】C18H26N2OS2 【 分 子 量 】350.54872 |
【开发单位】Pfizer (Originator) 【药理作用】ANALGESIC AND ANESTHETIC DRUGS, Analgesic Drugs, Non-Opioid Analgesics, Cyclooxygenase-2 Inhibitors, Non-Steroidal Antiinflammatory Drugs |
合成路线1
The reaction of 2,6-di(tert-butyl)phenol (I) with CS2 and ethyl chloroacetate gives the dithiobenzoate (II), which is treated with hydrazine in ethanol yielding the thiobenzoyl hydrazide (III). The cyclization of (III) with CS2 in refluxing ethanol affords the thiadiazolethione (IV), which is finally condensed with ethyl iodide and NaOH in THF.
| 【1】 Sercel, A.D.; Connor, D.T.; Song, Y.; et al.; Synthesis, structure-activity relationships, and in vivo evaluations of substituted di-tert-butylphenols as a novel class of potent, selective, and orally active cyclooxygenase-2 inhibitors. 2. 1,3,4- and 1,2,4-thiadiazole series. J Med Chem 1999, 42, 7, 1161. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10925 | Iodoethane;ethyl iod | 75-03-6 | C2H5I | 详情 | 详情 | |
| 16601 | ethyl chloroacetate; ethyl 2-chloroacetate | 105-39-5 | C4H7ClO2 | 详情 | 详情 | |
| (I) | 25925 | 2,6-di(tert-butyl)phenol | 128-39-2 | C14H22O | 详情 | 详情 |
| (II) | 25926 | ethyl 2-[[3,5-di(tert-butyl)-4-hydroxybenzothioyl]sulfanyl]acetate | C19H28O3S2 | 详情 | 详情 | |
| (III) | 25927 | 3,5-di(tert-butyl)-4-hydroxybenzenecarbothiohydrazide | C15H24N2OS | 详情 | 详情 | |
| (IV) | 25928 | 5-[3,5-di(tert-butyl)-4-hydroxyphenyl]-1,3,4-thiadiazole-2(3H)-thione | C16H22N2OS2 | 详情 | 详情 |
Extended Information