(S)-2-(1-(3-(1H-indol-3-yl)propanamido)-2-(4-(benzyloxy)phenyl)ethyl)-5-phenylthiazole-4-carboxylic acid | 1489279-29-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-2-(1-(3-(1H-indol-3-yl)propanamido)-2-(4-(benzyloxy)phenyl)ethyl)-5-phenylthiazole-4-carboxylic acid
• CAS: 1489279-29-9
• 化学式: C₃₆H₃₁N₃O₄S
• 分子量: 601.726
• InChiKey: PCTWGCMEJLEMER-HKBQPEDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  104.31
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(1-(3-(1H-indol-3-yl)propanamido)-2-(4-(benzyloxy)phenyl)ethyl)-5-phenylthiazole-4-carboxylic acid 在 N-甲基吗啉 、 lithium hydroxide monohydrate 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 (S)-2-(2-(1-(3-(1H-indol-3-yl)propanamido)-2-(4-(benzyloxy)phenyl)ethyl)-5-phenylthiazole-4-carboxamido)benzoic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 2-ethyl-5-phenylthiazole-4-carboxamide derivatives as protein tyrosine phosphatase 1B inhibitors with improved cellular efficacy

  摘要：

  Protein tyrosine phosphatase 1B (PTP1B) is implicated as a key negative regulator of the insulin and leptin signal-transduction pathways. PTP1B inhibitors have emerged as attractive and potent pharmaceutical agents for the treatment of type 2 diabetes and obesity. We identified a series of 2-ethy1-5-phenylthiazole-4-carboxamide (PTA) derivatives, inspired from the ACT scaffold of Scleritodermin A, as a novel class of PTP1B inhibitors. Structure-activity relationship (SAR) analysis and docking studies revealed the molecular basis of PTP1B inhibition by these compounds. PTA derivative 18g was capable of inhibiting intracellular PTP1B and subsequently activating the insulin signaling pathway. Treatment of cells with 18g markedly increased the phosphorylation levels of IRP and Akt as well as the rate of glucose uptake. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.017
• 作为产物：
  描述：

  benzoylaminoacetic acid ethyl ester 在 劳森试剂 、 甲醇 、 4-二甲氨基吡啶 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 (S)-2-(1-(3-(1H-indol-3-yl)propanamido)-2-(4-(benzyloxy)phenyl)ethyl)-5-phenylthiazole-4-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 2-ethyl-5-phenylthiazole-4-carboxamide derivatives as protein tyrosine phosphatase 1B inhibitors with improved cellular efficacy

  摘要：

  Protein tyrosine phosphatase 1B (PTP1B) is implicated as a key negative regulator of the insulin and leptin signal-transduction pathways. PTP1B inhibitors have emerged as attractive and potent pharmaceutical agents for the treatment of type 2 diabetes and obesity. We identified a series of 2-ethy1-5-phenylthiazole-4-carboxamide (PTA) derivatives, inspired from the ACT scaffold of Scleritodermin A, as a novel class of PTP1B inhibitors. Structure-activity relationship (SAR) analysis and docking studies revealed the molecular basis of PTP1B inhibition by these compounds. PTA derivative 18g was capable of inhibiting intracellular PTP1B and subsequently activating the insulin signaling pathway. Treatment of cells with 18g markedly increased the phosphorylation levels of IRP and Akt as well as the rate of glucose uptake. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.017