Lim In Taek, Brown Stephen, Mobashery Shahriar
Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
J Org Chem. 2004 May 14;69(10):3572-3. doi: 10.1021/jo049857v.
Compound 1, 2-(4-phenoxyphenylsulfonylmethyl)thiirane, is a potent and selective inhibitor for human gelatinases (J. Am. Chem. Soc. 2000, 122, 6799-6800), enzymes implicated in a number of diseases, including cancer. This compound is showing excellent promise in animal trials in a number of disease models. Large quantities of this compound were necessary for these studies. A convenient four-step synthetic route for compound 1 is described herein. The synthesis is amenable to scale-up to tens of grams and gives an overall yield of 57% for this important compound.
化合物1，即2-(4-苯氧基苯基磺酰甲基)硫杂环丙烷，是一种对人明胶酶具有强效且选择性的抑制剂（《美国化学会志》，2000年，第122卷，6799 - 6800页），明胶酶与包括癌症在内的多种疾病有关。该化合物在多个疾病模型的动物试验中显示出极佳的前景。这些研究需要大量的该化合物。本文描述了一种合成化合物1的简便的四步合成路线。该合成方法适合放大至几十克规模，对于这种重要化合物的总产率为57%。
