SB-3CT
[[(4-苯氧基苯基)磺酰基]甲基]噻丙环Chemical Name: 2-(4-Phenoxyphenylsulfonylmethyl)thiirane; 4-Phenoxyphenyl 2-thiiranylmethyl sulfone
CAS No. 292605-14-2
项目整合开发状态: Preclinical
项目研究机构: Wayne State University (Originator)
合成路线: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.
📌 参考资料/链接：
参考文献标题:Inhibitors of matrix metalloproteinases
文献作者:Mobashery,S.; Fridman,R.(Wayne State University)
参考来源:WO 0192244
📄 详细内容
合成路线: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.
参考文献标题:Potent and selective mechanism-based inhibition of gelatinases
文献作者:Kotra,L.P.; Brown,S.; Bernardo,M.M.; Tanaka,Y.; Li,Z.-H.; Fridman,R.; Mobashery,S.
参考来源:J Am Chem Soc 2000,122(28),6799
产品链接: CAS No. 292605-14-2››