Nussbaumer P, Petranyi G, Stütz A
Department of Dermatology, SANDOZ Forschungsinstitut, Wien, Austria.
J Med Chem. 1991 Jan;34(1):65-73. doi: 10.1021/jm00105a011.
Benzo[b]thiophene analogues of the allylamine antimycotic terbinafine (2) bearing the side chain at various positions and optionally substituted by halogen have been prepared and their antifungal activity studied. Derivatives bearing the side chain at positions 3, 4, or 7 are bioequivalents of 2. Compounds containing the allylamine side chain at position 7, with a further substituent at position 3, showed significantly enhanced activity against Candida albicans, an effect which appears to be specifically linked only to this particular substitution pattern. 3-Chloro-7-benzo[b]thienyl derivative 7m was found to be the most potent allylamine antimycotic identified so far. In general, substituted benzo[b]thiophenes can be used not only as potential equivalents of naphthalene in bioactive compounds but also as a tool to selectively modify biological activities.
制备了烯丙胺抗真菌药特比萘芬（2）的苯并[b]噻吩类似物，其侧链位于不同位置且可任选被卤素取代，并研究了它们的抗真菌活性。侧链位于3、4或7位的衍生物是2的生物等效物。7位含有烯丙胺侧链且3位有进一步取代基的化合物对白色念珠菌显示出显著增强的活性，这种效应似乎仅与这种特定的取代模式有特异性联系。发现3-氯-7-苯并[b]噻吩基衍生物7m是迄今为止鉴定出的最有效的烯丙胺抗真菌药。一般来说，取代的苯并[b]噻吩不仅可以用作生物活性化合物中萘的潜在等效物，还可以用作选择性修饰生物活性的工具。
