4-(phenethylthio)benzenesulfonamide | 1428673-40-8

• 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-(phenethylthio)benzenesulfonamide
• 英文别名: 4-[(2-Phenylethyl)Thio]Benzenesulfonamide；4-(2-phenylethylsulfanyl)benzenesulfonamide
• CAS: 1428673-40-8
• 化学式: C₁₄H₁₅NO₂S₂
• 分子量: 293.411
• InChiKey: BIDLYFNXVUUEMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  93.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,4'-二硫代二-苯磺酰氯 在 ammonium hydroxide 、 sodium tetrahydroborate 、 乙醇 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 4-(phenethylthio)benzenesulfonamide
  参考文献：
  名称：

  具有亚纳摩尔碳酸酐酶II和IX抑制特性的带有磺酰胺的不同硫骨架的合成及其抑制机理的X射线研究

  摘要：

  设计，合成和合成了几种具有不同硫代骨架的新分子，并对它们进行了碳酸酐酶（CAIs）抑制剂的生物学评估。结构-活性关系分析确定了硫醚衍生物（本文报道）是针对hCA II和hCA IX的有效和选择性的CAI。抑制剂结合的hCA II的高分辨率X射线结构揭示了与活性位点疏水口袋的广泛相互作用，并提供了对这些新抑制剂结合特性的分子洞察力。

  DOI：

  10.1016/j.bioorg.2018.09.028

文献信息

• 4-Substituted-2,3,5,6-tetrafluorobenzenesulfonamides as inhibitors of carbonic anhydrases I, II, VII, XII, and XIII
  作者：Virginija Dudutienė、Asta Zubrienė、Alexey Smirnov、Joana Gylytė、David Timm、Elena Manakova、Saulius Gražulis、Daumantas Matulis

  DOI：10.1016/j.bmc.2013.01.008

  日期：2013.4

  A series of 4-substituted-2,3,5,6-tetrafluorobenezenesulfonamides were synthesized and their binding potencies as inhibitors of recombinant human carbonic anhydrase isozymes I, II, VII, XII, and XIII were determined by the thermal shift assay, isothermal titration calorimetry, and stop-flow CO2 hydration assay. All fluorinated benzenesulfonamides exhibited nanomolar binding potency toward tested CAs and fluorinated benzenesulfonamides posessed higher binding potency than non-fluorinated compounds. The crystal structures of 4-[(4,6-dimethylpyrimidin-2-yl)thio]-2,3,5,6-tetrafluorobenzenesulfonamide in complex with CA II and CA XII, and 2,3,5,6-tetrafluoro-4-[(2-hydroxyethyl)sulfonyl]benzenesulfonamide in complex with CA XIII were determined. The observed dissociation constants for several fluorinated compounds reached subnanomolar range for CA I isozyme. The affinity and the selectivity of the compounds towards tested isozymes are presented. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of different thio-scaffolds bearing sulfonamide with subnanomolar carbonic anhydrase II and IX inhibitory properties and X-ray investigations for their inhibitory mechanism
  作者：Andrea Angeli、Damiano Tanini、Antonella Capperucci、Gianni Malevolti、Francesca Turco、Marta Ferraroni、Claudiu T. Supuran

  DOI：10.1016/j.bioorg.2018.09.028

  日期：2018.12

  inhibitors of Carbonic Anhydrases (CAIs). The structure-activity relationship analysis identified thioether derivatives, here reported, as a potent and selective CAIs against hCA II and hCA IX. High resolution X-ray structure of inhibitor bound hCA II revealed extensive interactions with the hydrophobic pocket of active site and provided molecular insight into the binding properties of these new inhibitors

  设计，合成和合成了几种具有不同硫代骨架的新分子，并对它们进行了碳酸酐酶（CAIs）抑制剂的生物学评估。结构-活性关系分析确定了硫醚衍生物（本文报道）是针对hCA II和hCA IX的有效和选择性的CAI。抑制剂结合的hCA II的高分辨率X射线结构揭示了与活性位点疏水口袋的广泛相互作用，并提供了对这些新抑制剂结合特性的分子洞察力。