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【结 构 式】 
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【药物名称】SB-3CT 【化学名称】2-(4-Phenoxyphenylsulfonylmethyl)thiirane 【CA登记号】292605-14-2 【 分 子 式 】C15H14O3S2 【 分 子 量 】306.40503 |
【开发单位】Wayne State University (Originator) 【药理作用】Oncolytic Drugs, Angiogenesis Inhibitors, MMP-2 (Gelatinase A) Inhibitors, MMP-9 (Gelatinase B) Inhibitors |
合成路线1
Treatment of 4-phenoxyphenol (I) with N,N-dimethylthiocarbamoyl chloride afforded the O-aryl thiocarbamate (II), which was thermally rearranged to the S-aryl thiocarbamate (III). Basic hydrolysis of (III) provided 4-phenoxythiophenol (IV). Subsequent alkylation of (IV) with allyl bromide (V) led to the allyl thioether (VI). Further oxidation of (VI) with m-chloroperbenzoic acid (MCPBA) gave rise to the epoxisulfone (VII). This was finally converted to the target thiirane derivative upon treatment with ammonium thiocyanate.
| 【1】 Kotra, L.P.; Brown, S.; Bernardo, M.M.; Tanaka, Y.; Li, Z.-H.; Fridman, R.; Mobashery, S.; Potent and selective mechanism-based inhibition of gelatinases. J Am Chem Soc 2000, 122, 28, 6799. |
| 【2】 Mobashery, S.; Fridman, R. (Wayne State University); Inhibitors of matrix metalloproteinases. WO 0192244 . |
| 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) | 27080 | 4-Phenoxyphenol | 831-82-3 | C12H10O2 | 详情 | 详情 |
| (II) | 27081 | O-(4-phenoxyphenyl) dimethylcarbamothioate | C15H15NO2S | 详情 | 详情 | |
| (III) | 46031 | S-(4-phenoxyphenyl) dimethylcarbamothioate | C15H15NO2S | 详情 | 详情 | |
| (IV) | 26254 | 4-phenoxybenzenethiol; 4-phenoxyphenylhydrosulfide | C12H10OS | 详情 | 详情 | |
| (V) | 11463 | 3-Bromo-1-propene; 3-Bromopropene；allyl bromide | 106-95-6 | C3H5Br | 详情 | 详情 |
| (VI) | 46032 | 1-(allylsulfanyl)-4-phenoxybenzene; 4-(allylsulfanyl)phenyl phenyl ether | C15H14OS | 详情 | 详情 | |
| (VII) | 46033 | 2-[[(4-phenoxyphenyl)sulfonyl]methyl]oxirane; 2-oxiranylmethyl 4-phenoxyphenyl sulfone | C15H14O4S | 详情 | 详情 |