SB-3CT-药物合成数据库

【药物名称】SB-3CT

化学结构式(Chemical Structure):

参考文献No.	52617
标题:	Inhibitors of matrix metalloproteinases
作者:	Mobashery, S.; Fridman, R. (Wayne State University)
来源:	WO 0192244

合成路线图解说明: 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.

参考文献No.	584477
标题:	Potent and selective mechanism-based inhibition of gelatinases
作者:	Kotra, L.P.; Brown, S.; Bernardo, M.M.; Tanaka, Y.; Li, Z.-H.; Fridman, R.; Mobashery, S.
来源:	J Am Chem Soc 2000,122(28),6799

合成路线图解说明: 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.