1,1,1-trifluoro-N-phenoxathiin-2-yl-methanesulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 1,1,1-trifluoro-N-phenoxathiin-2-yl-methanesulfonamide
• 英文别名: 1,1,1-trifluoro-N-phenoxathiin-2-ylmethanesulfonamide
• 化学式: C₁₃H₈F₃NO₃S₂
• 分子量: 347.339
• InChiKey: ZCNVRIMQEIEYQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  89.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-aminophenoxathiin 、 三氟甲磺酸酐 以 丙酮 为溶剂， 反应 15.0h， 以60%的产率得到1,1,1-trifluoro-N-phenoxathiin-2-yl-methanesulfonamide
  参考文献：
  名称：

  The antifungal activity of sulfonylamido derivatives of 2-aminophenoxathiin and related compounds

  摘要：

  Aryl/alkyl-sulfonylamido, arylsulfenylamido, arylcarboxamido and ureido/thioureido derivatives of 2-aminophenoxathiin were prepared by reaction of the title compound with sulfonyl/sulfenyl halides, sulfonic acid anhydrides, acyl chlorides, tosyl isocyanate, aryl/allyl isocyanates or isothiocyanates. Some of these derivatives, containing free amino groups, have been further derivatized by reaction with 2,4,6-trisubstituted-pyrylium salts, aryl/allyl isocyanate/isothiocyanates or tosyl isocyanate. Several of the newly synthesized compounds act as effective antifungal agents against Aspergillus and Candida spp., some of them showing activities comparable to ketoconazole or itraconazole (against the aspergilli) but being much less effective against Candida. The mechanism of action of these compounds involves inhibition of ergosterol biosynthesis, and probably interaction with lanosterol-14-alpha-demethylase (CYP51A1), since reduced amounts of ergosterol were evidenced by means of HPLC in cultures of the sensitive strain A. niger treated with some of these inhibitors. Thus, the two classes of antifungal compounds, i.e. the azoles and the new derivatives reported here, might possess a similar mechanism of action at molecular level. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80034-8

文献信息

• The antifungal activity of sulfonylamido derivatives of 2-aminophenoxathiin and related compounds
  作者：Claudiu T. Supuran、Andrea Scozzafava、Fabrizio Briganti、George Loloiu、Ovidiu Maior

  DOI：10.1016/s0223-5234(99)80034-8

  日期：1998.10

  Aryl/alkyl-sulfonylamido, arylsulfenylamido, arylcarboxamido and ureido/thioureido derivatives of 2-aminophenoxathiin were prepared by reaction of the title compound with sulfonyl/sulfenyl halides, sulfonic acid anhydrides, acyl chlorides, tosyl isocyanate, aryl/allyl isocyanates or isothiocyanates. Some of these derivatives, containing free amino groups, have been further derivatized by reaction with 2,4,6-trisubstituted-pyrylium salts, aryl/allyl isocyanate/isothiocyanates or tosyl isocyanate. Several of the newly synthesized compounds act as effective antifungal agents against Aspergillus and Candida spp., some of them showing activities comparable to ketoconazole or itraconazole (against the aspergilli) but being much less effective against Candida. The mechanism of action of these compounds involves inhibition of ergosterol biosynthesis, and probably interaction with lanosterol-14-alpha-demethylase (CYP51A1), since reduced amounts of ergosterol were evidenced by means of HPLC in cultures of the sensitive strain A. niger treated with some of these inhibitors. Thus, the two classes of antifungal compounds, i.e. the azoles and the new derivatives reported here, might possess a similar mechanism of action at molecular level. (C) Elsevier, Paris.