4-{[4-(methoxycarbonyl)phenyl]carbonylamino}benzoic acid | 380365-18-4

• 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-(methoxycarbonyl)phenyl]carbonylamino}benzoic acid
• 英文别名: 4-{[4-(Methoxycarbonyl)benzoyl]amino}benzoic acid；4-[(4-methoxycarbonylbenzoyl)amino]benzoic acid
• CAS: 380365-18-4
• 化学式: C₁₆H₁₃NO₅
• 分子量: 299.283
• InChiKey: BHEFJWMLPDOMFL-UHFFFAOYSA-N

物化性质

• 沸点：
  431.5±30.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-{[4-(methoxycarbonyl)phenyl]carbonylamino}benzoic acid 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 生成 methyl N-{4-[4-(thiazol-2-ylsulfonylamino)phenylcarbamoyl]phenyl}-p-aminocarbonylbenzoate
  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：

  对苯二甲酸单甲酯 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-{[4-(methoxycarbonyl)phenyl]carbonylamino}benzoic acid
  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

文献信息

• Substituted stilbenes as glucose uptake enhancers
  申请人：——

  公开号：US20020032218A1

  公开（公告）日：2002-03-14

  Compounds of formula I activate the insulin receptor kinase. Pharmaceutical compositions comprising the compounds, and methods of treatment of hyperglycemia and other diseases involving imbalance of glucose levels, especially for the treatment of type II diabetes, by administering these compounds to mannnalian hosts, and processes for their preparation, are also described.

  式I的化合物能激活胰岛素受体激酶。包括这些化合物的药物组合物，以及治疗高血糖和其他涉及葡萄糖水平失衡的疾病的方法，特别是治疗2型糖尿病的方法，通过向哺乳动物宿主投药这些化合物，并描述了它们的制备过程。
• Oxindole hydrazide modulators of protein tyrosine phosphatases (ptps)
  申请人：Bombrun Agnes

  公开号：US20050043388A1

  公开（公告）日：2005-02-24

  The present invention is related to the use of oxindole hydrazide derivatives of formula (I) for the treatment and/or prevention of metabolic disorders mediated by insulin resistance or hyperglycemia, comprising diabetes type I and/or II, inadequate glucose tolerance, insulin resistance, hyperlipidemia, hypertriglyceridemia, hypercholesterolemia, obesity, polycystic ovary syndrome (PCOS). In particular, the present invention is related to the use of oxindole hydrazide derivatives of formula (I) to modulate, notably to inhibit the activity of PTPs, in particular of PTP1B, TC-PTP, SHP and GLEPP-1. The present invention is furthermore related to novel oxindole hydrazide derivatives and method of preparation thereof.(I).

  本发明涉及使用式(I)的氧化吲哚肼衍生物治疗和/或预防由胰岛素抵抗或高血糖介导的代谢紊乱，包括1型和/或2型糖尿病、不适当的葡萄糖耐受性、胰岛素抵抗、高脂血症、高三酰甘油血症、高胆固醇血症、肥胖症、多囊卵巢综合症（PCOS）。特别地，本发明涉及使用式(I)的氧化吲哚肼衍生物来调节，特别是抑制PTPs的活性，特别是PTP1B、TC-PTP、SHP和GLEPP-1。本发明还涉及新的氧化吲哚肼衍生物及其制备方法。
• OXINDOLE HYDRAZIDE MODULATORS OF PROTEIN TYROSINE PHOSPHATASES (PTPS)
  申请人：BOMBRUN Agnes

  公开号：US20100168101A1

  公开（公告）日：2010-07-01

  The present invention is related to the use of oxindole hydrazide derivatives of formula (I) for the treatment and/or prevention of metabolic disorders mediated by insulin resistance or hyperglycemia, comprising diabetes type I and/or II, inadequate glucose tolerance, insulin resistance, hyperlipidemia, hypertriglyceridemia, hypercholesterolemia, obesity, polycystic ovary syndrome (PCOS). In particular, the present invention is related to the use of oxindole hydrazide derivatives of formula (I) to modulate, notably to inhibit the activity of PTPs, in particular of PTP1B, TC-PTP, SHP and GLEPP-1. The present invention is furthermore related to novel oxindole hydrazide derivatives and method of preparation thereof.

  本发明涉及使用式(I)的氧化吲哚肼衍生物治疗和/或预防由胰岛素抵抗或高血糖介导的代谢障碍，包括1型和/或2型糖尿病、不足的葡萄糖耐受性、胰岛素抵抗、高脂血症、高三酰甘油血症、高胆固醇血症、肥胖和多囊卵巢综合症（PCOS）。特别地，本发明涉及使用式(I)的氧化吲哚肼衍生物调节，特别是抑制PTP的活性，尤其是PTP1B、TC-PTP、SHP和GLEPP-1的活性。本发明还涉及新的氧化吲哚肼衍生物及其制备方法。
• Oxindole hydrazide modulators of protein tyrosine phosphatases (PTPs)
  申请人：Laboratoires Serono SA

  公开号：US07696231B2

  公开（公告）日：2010-04-13

  The present invention is related to the use of oxindole hydrazide derivatives of formula (I) for the treatment and/or prevention of metabolic disorders mediated by insulin resistance or hyperglycemia, comprising diabetes type I and/or II, inadequate glucose tolerance, insulin resistance, hyperlipidemia, hypertriglyceridemia, hypercholesterolemia, obesity, polycystic ovary syndrome (PCOS). In particular, the present invention is related to the use of oxindole hydrazide derivatives of formula (I) to modulate, notably to inhibit the activity of PTPs, in particular of PTP1B, TC-PTP, SHP and GLEPP-1. The present invention is furthermore related to novel oxindole hydrazide derivatives and method of preparation thereof.(I).

  本发明涉及使用式(I)的氧化吲哚肼衍生物治疗和/或预防由胰岛素抵抗或高血糖介导的代谢紊乱，包括1型和/或2型糖尿病、不足的葡萄糖耐受性、胰岛素抵抗、高脂血症、高甘油三酯血症、高胆固醇血症、肥胖症、多囊卵巢综合症（PCOS）。具体而言，本发明涉及使用式(I)的氧化吲哚肼衍生物来调节，特别是抑制PTPs的活性，特别是PTP1B、TC-PTP、SHP和GLEPP-1。本发明还涉及新的氧化吲哚肼衍生物及其制备方法。(I)。
• US6479548B2
  申请人：——

  公开号：US6479548B2

  公开（公告）日：2002-11-12