methyl 3-(4-(2-chlorophenyl)phenyl)propanoate

• 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: methyl 3-(4-(2-chlorophenyl)phenyl)propanoate
• 英文别名: Methyl 3-[4-(2-chlorophenyl)phenyl]propanoate
• 化学式: C₁₆H₁₅ClO₂
• 分子量: 274.747
• InChiKey: SXJNRLHVDGERPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-(2-chlorophenyl)phenyl)propanoate 在 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以100%的产率得到3-(2'-chloro-[1,1'-biphenyl]-4-yl)propanoic acid
  参考文献：
  名称：

  Affinity and kinetics study of anthranilic acids as HCA2 receptor agonists

  摘要：

  Structure-affinity relationship (SAR) and structure-kinetics relationship (SKR) studies were combined to investigate a series of biphenyl anthranilic acid agonists for the HCA(2) receptor. In total, 27 compounds were synthesized and twelve of them showed higher affinity than nicotinic acid. Two compounds, 6g (IC50 = 75 nM) and 6z (IC50 = 108 nM) showed a longer residence time profile compared to nicotinic acid, exemplified by their kinetic rate index (KRI) values of 1.31 and 1.23, respectively. The SAR study resulted in the novel 2-F, 4-OH derivative (6x) with an IC50 value of 23 nM as the highest affinity HCA(2) agonist of the biphenyl series, although it showed a similar residence time as nicotinic acid. The SAR and SKR data suggest that an early compound selection based on binding kinetics is a promising addition to the lead optimization process. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.02.018
• 作为产物：
  描述：

  2-氯苯基硼酸 、 3-(4-溴苯基)丙酸甲酯 在 四(三苯基膦)钯 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 3.0h， 以93%的产率得到methyl 3-(4-(2-chlorophenyl)phenyl)propanoate
  参考文献：
  名称：

  Affinity and kinetics study of anthranilic acids as HCA2 receptor agonists

  摘要：

  Structure-affinity relationship (SAR) and structure-kinetics relationship (SKR) studies were combined to investigate a series of biphenyl anthranilic acid agonists for the HCA(2) receptor. In total, 27 compounds were synthesized and twelve of them showed higher affinity than nicotinic acid. Two compounds, 6g (IC50 = 75 nM) and 6z (IC50 = 108 nM) showed a longer residence time profile compared to nicotinic acid, exemplified by their kinetic rate index (KRI) values of 1.31 and 1.23, respectively. The SAR study resulted in the novel 2-F, 4-OH derivative (6x) with an IC50 value of 23 nM as the highest affinity HCA(2) agonist of the biphenyl series, although it showed a similar residence time as nicotinic acid. The SAR and SKR data suggest that an early compound selection based on binding kinetics is a promising addition to the lead optimization process. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.02.018

文献信息

• COMPOUNDS FOR THE TREATMENT OF METABOLIC DISEASES
  申请人：Ulven Trond

  公开号：US20110152315A1

  公开（公告）日：2011-06-23

  There is provided novel compounds capable of modulating the G-protein-coupled receptor GPR40, compositions comprising the compounds, and methods for their use for controlling insulin levels in vivo and for the treatment of conditions such as type I1 diabetes, hypertension, ketoacidosis, obesity, glucose intolerance, and hypercholesterolemia and related disorders associated with abnormally high or low plasma lipoprotein, triglyceride or glucose levels.

  提供了一种新的化合物，能够调节G蛋白偶联受体GPR40，包括该化合物的组合物以及使用它们的方法，用于控制体内胰岛素水平和治疗诸如2型糖尿病、高血压、酮症酸中毒、肥胖症、葡萄糖耐受性不良以及与异常高或低血浆脂蛋白、甘油三酯或葡萄糖水平有关的相关疾病。
• Affinity and kinetics study of anthranilic acids as HCA2 receptor agonists
  作者：Jacobus P.D. van Veldhoven、Rongfang Liu、Stephanie A. Thee、Yessica Wouters、Sanne J.M. Verhoork、Christiaan Mooiman、Julien Louvel、Adriaan P. IJzerman

  DOI：10.1016/j.bmc.2015.02.018

  日期：2015.7

  Structure-affinity relationship (SAR) and structure-kinetics relationship (SKR) studies were combined to investigate a series of biphenyl anthranilic acid agonists for the HCA(2) receptor. In total, 27 compounds were synthesized and twelve of them showed higher affinity than nicotinic acid. Two compounds, 6g (IC50 = 75 nM) and 6z (IC50 = 108 nM) showed a longer residence time profile compared to nicotinic acid, exemplified by their kinetic rate index (KRI) values of 1.31 and 1.23, respectively. The SAR study resulted in the novel 2-F, 4-OH derivative (6x) with an IC50 value of 23 nM as the highest affinity HCA(2) agonist of the biphenyl series, although it showed a similar residence time as nicotinic acid. The SAR and SKR data suggest that an early compound selection based on binding kinetics is a promising addition to the lead optimization process. (C) 2015 Elsevier Ltd. All rights reserved.