N-(4-[1,2,3]Thiadiazol-4-yl-benzyl)-benzenesulfonamide | 253308-55-3

• 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: N-(4-[1,2,3]Thiadiazol-4-yl-benzyl)-benzenesulfonamide
• 英文别名: N-[[4-(thiadiazol-4-yl)phenyl]methyl]benzenesulfonamide
• CAS: 253308-55-3
• 化学式: C₁₅H₁₃N₃O₂S₂
• 分子量: 331.419
• InChiKey: NUMSMHYOIZXZHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-[1,2,3]Thiadiazol-4-yl-benzyl)-benzenesulfonamide 在 三甲基溴硅烷 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 [(4-{[Benzenesulfonyl-(4-[1,2,3]thiadiazol-4-yl-benzyl)-amino]-methyl}-phenyl)-difluoro-methyl]-phosphonic acid
  参考文献：
  名称：

  Discovery and structure–activity relationships of novel sulfonamides as potent PTP1B inhibitors

  摘要：

  A series of novel sulfonamides containing a single difluoromethylene-phosphonate group were discovered to be potent inhibitors of protein tyrosine phosphatase 1B. Structure-activity relationships around the scaffold were investigated, leading to the identification of compounds with IC50 or K-i values in the low nanomolar range. These sulfonamide-based inhibitors exhibit 100 and 30 times higher inhibitory activity than the corresponding tertiary amines and carboxamides, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.061
• 作为产物：
  描述：

  苯磺酰氯 、 [4-(1,2,3-thiadiazol-4-yl)phenyl]methanamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-[1,2,3]Thiadiazol-4-yl-benzyl)-benzenesulfonamide
  参考文献：
  名称：

  Discovery and structure–activity relationships of novel sulfonamides as potent PTP1B inhibitors

  摘要：

  A series of novel sulfonamides containing a single difluoromethylene-phosphonate group were discovered to be potent inhibitors of protein tyrosine phosphatase 1B. Structure-activity relationships around the scaffold were investigated, leading to the identification of compounds with IC50 or K-i values in the low nanomolar range. These sulfonamide-based inhibitors exhibit 100 and 30 times higher inhibitory activity than the corresponding tertiary amines and carboxamides, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.061

文献信息

• Discovery and structure–activity relationships of novel sulfonamides as potent PTP1B inhibitors
  作者：Christopher P. Holmes、Xianfeng Li、Yijun Pan、Caiding Xu、Ashok Bhandari、Claire M. Moody、Joy A. Miguel、Steven W. Ferla、M. Nuria De Francisco、Brian T. Frederick、Siqun Zhou、Natalie Macher、Larry Jang、Jennifer D. Irvine、J. Russell Grove

  DOI：10.1016/j.bmcl.2005.06.061

  日期：2005.10

  A series of novel sulfonamides containing a single difluoromethylene-phosphonate group were discovered to be potent inhibitors of protein tyrosine phosphatase 1B. Structure-activity relationships around the scaffold were investigated, leading to the identification of compounds with IC50 or K-i values in the low nanomolar range. These sulfonamide-based inhibitors exhibit 100 and 30 times higher inhibitory activity than the corresponding tertiary amines and carboxamides, respectively. (c) 2005 Elsevier Ltd. All rights reserved.
• PTP1B inhibitors: Synthesis and evaluation of difluoro-methylenephosphonate bioisosteres on a sulfonamide scaffold
  作者：Christopher P. Holmes、Xianfeng Li、Yijun Pan、Caiding Xu、Ashok Bhandari、Claire M. Moody、Joy A. Miguel、Steven W. Ferla、M. Nuria De Francisco、Brian T. Frederick、Siqun Zhou、Natalie Macher、Larry Jang、Jennifer D. Irvine、J. Russell Grove

  DOI：10.1016/j.bmcl.2008.03.007

  日期：2008.4

  We have synthesized and evaluated a series of triaryl sulfonamide-based PTP1B inhibitors in which a difluoro-methylenephosphonate group of a potent lead has been replaced by potential bioisosteric replacements. Several mono-or di-charged compounds (8a, 8b, and 15a) were shown exhibit inhibitory activity in the low micromolar range, demonstrating the feasibility of using this approach in identifying non-phosphonate pTyr mimetics in a small molecular scaffold. These results also provide a useful indication of the relative effectiveness of these pTyr mimetics. (C) 2008 Elsevier Ltd. All rights reserved.