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【结 构 式】

【药物名称】SB-3CT

【化学名称】2-(4-Phenoxyphenylsulfonylmethyl)thiirane
      4-Phenoxyphenyl 2-thiiranylmethyl sulfone

【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
Extended Information