2-[1-[4-[[4-(dimethylamino)benzoyl]amino]benzoyl]isoquinolin-4-yl]acetic acid | 1233246-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2-[1-[4-[[4-(dimethylamino)benzoyl]amino]benzoyl]isoquinolin-4-yl]acetic acid
• 英文别名: 2-[1-[4-[[4-(Dimethylamino)benzoyl]amino]benzoyl]isoquinolin-4-yl]acetic acid
• CAS: 1233246-80-4
• 化学式: C₂₇H₂₃N₃O₄
• 分子量: 453.497
• InChiKey: KOUCLTRRCYOAMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  99.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对氨基苯乙腈 在 吡啶 、 草酰氯 、 水 、 silver(I) acetate 、 sodium hexamethyldisilazane 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 62.0h， 生成 2-[1-[4-[[4-(dimethylamino)benzoyl]amino]benzoyl]isoquinolin-4-yl]acetic acid
  参考文献：
  名称：

  Isoquinoline derivatives as potent CRTH2 antagonists: Design, synthesis and SAR

  摘要：

  In this study, we describe the synthesis and structure-activity relationship (SAR) of a series of isoquinoline chemoattractant receptor-homologous molecule expressed on Th2 cells (CRTH2) antagonists. TASP0376377 (15-20), one of the most potent compounds, showed a potent binding affinity (IC50 = 19 nM) in addition to the excellent functional antagonist activity (IC50 = 13 nM). Moreover, the efficacy of this compound in a chemotaxis assay (IC50 = 23 nM) was in good agreement with its potency as a CRTH2 antagonist. In addition, 15-20 exhibited greater selectivity in binding to CRTH2 than to the DP1 prostanoid receptor (IC50 > 1 mu M) or the enzymes COX-1 and COX-2 (IC50 > 10 mu M). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.025

文献信息

• Isoquinoline derivatives as potent CRTH2 antagonists: Design, synthesis and SAR
  作者：Rie Nishikawa-Shimono、Yoshinori Sekiguchi、Takeshi Koami、Madoka Kawamura、Daisuke Wakasugi、Kazuhito Watanabe、Shunichi Wakahara、Kayo Kimura、Susumu Yamanobe、Tetsuo Takayama

  DOI：10.1016/j.bmc.2013.10.025

  日期：2013.12

  In this study, we describe the synthesis and structure-activity relationship (SAR) of a series of isoquinoline chemoattractant receptor-homologous molecule expressed on Th2 cells (CRTH2) antagonists. TASP0376377 (15-20), one of the most potent compounds, showed a potent binding affinity (IC50 = 19 nM) in addition to the excellent functional antagonist activity (IC50 = 13 nM). Moreover, the efficacy of this compound in a chemotaxis assay (IC50 = 23 nM) was in good agreement with its potency as a CRTH2 antagonist. In addition, 15-20 exhibited greater selectivity in binding to CRTH2 than to the DP1 prostanoid receptor (IC50 > 1 mu M) or the enzymes COX-1 and COX-2 (IC50 > 10 mu M). (C) 2013 Elsevier Ltd. All rights reserved.