3-(1H-tetrazol-5-yl)benzenesulfonyl chloride | 476362-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(1H-tetrazol-5-yl)benzenesulfonyl chloride
• 英文别名: 3-(1H-1,2,3,4-tetrazol-5-yl)benzene-1-sulfonyl chloride；3-(2H-tetrazol-5-yl)benzenesulfonyl chloride
• CAS: 476362-71-7
• 化学式: C₇H₅ClN₄O₂S
• mdl: MFCD10697734
• 分子量: 244.661
• InChiKey: VKJSATBJGQJEET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(苯磺酰基)-N-(哌啶-4-基)-2-(三氟甲基)苯磺酰胺; WAY 316606 、 3-(1H-tetrazol-5-yl)benzenesulfonyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 5-(phenylsulfonyl)-N-(1-([3-(2H-tetrazol-5-yl)phenyl]-sulfonyl)piperidin-4-yl)-2-(trifluoromethyl)benzenesulfonamide
  参考文献：
  名称：

  Modulation of Wnt signaling through inhibition of secreted frizzled-related protein I (sFRP-1) with N-substituted piperidinyl diphenylsulfonyl sulfonamides: Part II

  摘要：

  Piperidinyl diphenylsulfonyl sulfonamides are a novel class of molecules that have inhibitory binding affinity for sFRP-1. As a secreted protein sFRP-1 inhibits the function of the secreted Wnt glycoprotein. Therefore, as inhibitors of sFRP-1 these small molecules facilitate the Wnt/beta-catenin canonical signaling pathway. Details of the structure-activity relationships and biological activity of this structural class of compounds will be discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.11.002
• 作为产物：
  描述：

  5-(3-氨基苯基)四唑 在 盐酸 、 溶剂黄146 、 sodium nitrite 、 二氧化硫 、 copper(l) chloride 作用下， 以 水 为溶剂， 反应 0.25h， 以68%的产率得到3-(1H-tetrazol-5-yl)benzenesulfonyl chloride
  参考文献：
  名称：

  Identification of Potent and Selective Small-Molecule Inhibitors of Caspase-3 through the Use of Extended Tethering and Structure-Based Drug Design

  摘要：

  The design, synthesis, and in vitro activities of a series of potent and selective small-molecule inhibitors of caspase-3 are described. From extended tethering, a salicylic acid fragment was identified as having binding affinity for the S-4 pocket of caspase-3. X-ray crystallography and molecular modeling of the initial tethering hit resulted in the synthesis of 4, which reversibly inhibited caspase-3 with a K-i = 40 nM. Further optimization led to the identification of a series of potent and selective inhibitors with K-i values in the 20-50 nM range. One of the most potent compounds in this series, 66b, inhibited caspase-3 with a K-i = 20 nM and selectivity of 8-500-fold for caspase-3 vs a panel of seven caspases (1, 2, and 4-8). A high-resolution X-ray cocrystal structure of 4 and 66b supports the predicted binding modes of our compounds with caspase-3.

  DOI：

  10.1021/jm020230j