{ethanesulfonyl-[4-({[4-(4-ethoxybenzenesulfonylamino)phenyl]phenylmethanesulfonylamino}methyl)phenyl]amino}acetic acid methyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {ethanesulfonyl-[4-({[4-(4-ethoxybenzenesulfonylamino)phenyl]phenylmethanesulfonylamino}methyl)phenyl]amino}acetic acid methyl ester
• 英文别名: methyl 2-[4-[[N-benzylsulfonyl-4-[(4-ethoxyphenyl)sulfonylamino]anilino]methyl]-N-ethylsulfonylanilino]acetate
• 化学式: C₃₃H₃₇N₃O₉S₃
• 分子量: 715.869
• InChiKey: UZZUVIVTTDXMEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  182
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  苯乙醚 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 {ethanesulfonyl-[4-({[4-(4-ethoxybenzenesulfonylamino)phenyl]phenylmethanesulfonylamino}methyl)phenyl]amino}acetic acid methyl ester
  参考文献：
  名称：

  Novel, potent, selective and cellular active ABC type PTP1B inhibitors containing (methanesulfonyl-phenyl-amino)-acetic acid methyl ester phosphotyrosine mimetic

  摘要：

  Protein tyrosine phosphatase 1B (PTP1B) which plays an important role in the negative regulation of insulin and leptin pathway has emerged as a novel promising therapeutic target for the treatment of type 2 diabetes mellitus and obesity. Upon careful study, a series of novel scaffold and simple synthesis method inhibitors were discovered based on the analysis of X-ray crystal structures of PTP1B/inhibitor complexes and docking simulations. Among them, compound P7 exhibited high inhibitory activity (IC50 = 222 nM) with moderate selectivity (8-fold) over T-cell PTPase (TCPTP) through interacting with the A, B and C binding sites of PTP1B enzyme. Further studies on cellular activities revealed that compound P7 could enhance insulin-mediated in phosphorylation and insulin-stimulated glucose uptake. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.09.024

文献信息

• Novel, potent, selective and cellular active ABC type PTP1B inhibitors containing (methanesulfonyl-phenyl-amino)-acetic acid methyl ester phosphotyrosine mimetic
  作者：Peihong Liu、Yongli Du、Lianhua Song、Jingkang Shen、Qunyi Li

  DOI：10.1016/j.bmc.2015.09.024

  日期：2015.11

  Protein tyrosine phosphatase 1B (PTP1B) which plays an important role in the negative regulation of insulin and leptin pathway has emerged as a novel promising therapeutic target for the treatment of type 2 diabetes mellitus and obesity. Upon careful study, a series of novel scaffold and simple synthesis method inhibitors were discovered based on the analysis of X-ray crystal structures of PTP1B/inhibitor complexes and docking simulations. Among them, compound P7 exhibited high inhibitory activity (IC50 = 222 nM) with moderate selectivity (8-fold) over T-cell PTPase (TCPTP) through interacting with the A, B and C binding sites of PTP1B enzyme. Further studies on cellular activities revealed that compound P7 could enhance insulin-mediated in phosphorylation and insulin-stimulated glucose uptake. (C) 2015 Elsevier Ltd. All rights reserved.