4-[(4-nitrophenyl)methylamino]-N-(1,3-thiazol-2-yl)benzenesulfonamide | 1429056-07-4

• 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-[(4-nitrophenyl)methylamino]-N-(1,3-thiazol-2-yl)benzenesulfonamide
• CAS: 1429056-07-4
• 化学式: C₁₆H₁₄N₄O₄S₂
• 分子量: 390.444
• InChiKey: ASLSLVZNLUVNHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  154
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[(4-nitrophenyl)methylamino]-N-(1,3-thiazol-2-yl)benzenesulfonamide 在 sodium tetrahydroborate 、 palladium 10% on activated carbon 、 三乙胺 、 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 生成 4-methoxy-N-[4-[[4-(1,3-thiazol-2-ylsulfamoyl)anilino]methyl]phenyl]benzamide
  参考文献：
  名称：

  Design, synthesis and insulin-sensitising effects of novel PTP1B inhibitors

  摘要：

  Fifteen novel sulfathiazole-related compounds were designed as PTP1B inhibitors based on a previously reported allosteric inhibitor (1) of PTP1B. These compounds were synthesized and evaluated against human recombinant PTP1B. Six compounds (3, 4, 8 and 14-16) exhibited significant inhibitory activity against PTP1B. The most active compound (16) showed IC50 value of 3.2 mu M and kinetic analysis indicated that it is a non-competitive inhibitor of PTP1B. Furthermore, compound 16 demonstrated excellent selectivity to PTP1B over other PTPs. It also displayed in vivo insulin sensitizing effect in the insulin resistant mice. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.073
• 作为产物：
  描述：

  磺胺噻唑 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 4-[(4-nitrophenyl)methylamino]-N-(1,3-thiazol-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Design, synthesis and insulin-sensitising effects of novel PTP1B inhibitors

  摘要：

  Fifteen novel sulfathiazole-related compounds were designed as PTP1B inhibitors based on a previously reported allosteric inhibitor (1) of PTP1B. These compounds were synthesized and evaluated against human recombinant PTP1B. Six compounds (3, 4, 8 and 14-16) exhibited significant inhibitory activity against PTP1B. The most active compound (16) showed IC50 value of 3.2 mu M and kinetic analysis indicated that it is a non-competitive inhibitor of PTP1B. Furthermore, compound 16 demonstrated excellent selectivity to PTP1B over other PTPs. It also displayed in vivo insulin sensitizing effect in the insulin resistant mice. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.073