4-(2-Methanesulfonyl-ethyl)-thiobenzamide | 872057-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(2-Methanesulfonyl-ethyl)-thiobenzamide
• CAS: 872057-00-6
• 化学式: C₁₀H₁₃NO₂S₂
• 分子量: 243.351
• InChiKey: RBCIBATURGZXCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.16
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(2-Methanesulfonyl-ethyl)-thiobenzamide 在 ammonium acetate 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 4-(2-Methanesulfonyl-ethyl)-benzamidine
  参考文献：
  名称：

  Design, synthesis, and evaluation of oxyanion-hole selective inhibitor substituents for the S1 subsite of factor Xa

  摘要：

  We have designed, synthesized, and evaluated the factor Xa inhibitory activities of p-amidinophenyl-sulfones, amines, and alcohols intended to take advantage of the polarity and hydrogen-bonding potential of the oxyanion hole region of the S1 specificity pocket. We demonstrate that placement of an anionic group within the oxyanion bole region of the catalytic site substantially enhances activity, with small flexible groups favored over bulkier ones. Ab initio pK(a) calculations suggest that the hydroxyl substituent frequently used for benzamidine moieties may be ionized to form an anionic group, consistent with the general trend. One nonamidine based substituent also shows promising activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.054
• 作为产物：
  描述：

  4-(2-Methanesulfonyl-ethyl)-benzonitrile 在 O,S-diethyl-dithiophosphoric acid 、 水 作用下， 以98%的产率得到4-(2-Methanesulfonyl-ethyl)-thiobenzamide
  参考文献：
  名称：

  Design, synthesis, and evaluation of oxyanion-hole selective inhibitor substituents for the S1 subsite of factor Xa

  摘要：

  We have designed, synthesized, and evaluated the factor Xa inhibitory activities of p-amidinophenyl-sulfones, amines, and alcohols intended to take advantage of the polarity and hydrogen-bonding potential of the oxyanion hole region of the S1 specificity pocket. We demonstrate that placement of an anionic group within the oxyanion bole region of the catalytic site substantially enhances activity, with small flexible groups favored over bulkier ones. Ab initio pK(a) calculations suggest that the hydroxyl substituent frequently used for benzamidine moieties may be ionized to form an anionic group, consistent with the general trend. One nonamidine based substituent also shows promising activity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.054