4-{[4-(2-methoxy-2-oxoethyl)isoquinolin-l-yl]carbonyl}benzoic acid | 1233249-60-9

• 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: 4-{[4-(2-methoxy-2-oxoethyl)isoquinolin-l-yl]carbonyl}benzoic acid
• 英文别名: 4-[4-(2-Methoxy-2-oxoethyl)isoquinoline-1-carbonyl]benzoic acid
• CAS: 1233249-60-9
• 化学式: C₂₀H₁₅NO₅
• 分子量: 349.343
• InChiKey: NVNXYLQQXPBNLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  93.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-{[4-(2-methoxy-2-oxoethyl)isoquinolin-l-yl]carbonyl}benzoic acid 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 为溶剂， 反应 15.0h， 生成 methyl 2-(1-(4-((3,4-dichlorophenyl)carbamoyl)benzoyl)isoquinolin-4-yl)acetate
  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
• 作为产物：
  描述：

  tert-butyl 4-{[4-(2-methoxy-2-oxoethyl)isoquinolin-1-yl]carbonyl}benzoate 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 4-{[4-(2-methoxy-2-oxoethyl)isoquinolin-l-yl]carbonyl}benzoic acid
  参考文献：
  名称：

  EP2377851

  摘要：

  公开号：

文献信息

• ISOQUINOLINE DERIVATIVE
  申请人：Takayama Tetsuo

  公开号：US20110288293A1

  公开（公告）日：2011-11-24

  A compound represented by formula (I) or a pharmaceutically acceptable salt thereof has an effect of inhibiting CRTH2 and, therefore, is useful as a preventive or a remedy for allergic diseases such as asthma, atopic dermatitis and allergic rhinitis.

  化合物(I)的分子式或其药学上可接受的盐具有抑制CRTH2的效果，因此可用作预防或治疗哮喘、特应性皮炎和过敏性鼻炎等过敏性疾病的药物。
• Isoquinoline derivatives as potent CRTH2 receptor antagonists: Synthesis and SAR
  作者：Rie Nishikawa-Shimono、Yoshinori Sekiguchi、Takeshi Koami、Madoka Kawamura、Daisuke Wakasugi、Kazuhito Watanabe、Shunichi Wakahara、Kayo Matsumoto、Tetsuo Takayama

  DOI：10.1016/j.bmcl.2012.03.009

  日期：2012.5

  Synthesis and structure-activity relationship of a novel series of isoquinoline CRTH2 receptor antagonists are described. One of the most potent compounds, TASP0376377 (6m), showed not only potent binding affinity (IC50 = 19 nM) but also excellent functional antagonist activity (IC50 = 13 nM). TASP0376377 was tested for its ability of a chemotaxis assay to show the effectiveness (IC50 = 23 nM), which was in good agreement with the CRTH2 antagonist potency. Furthermore, TASP0376377 showed sufficient selectivity for binding to CRTH2 over the DP1 prostanoid receptor (IC50 > 1 mu M) and COX-1 and COX-2 enzymes (IC50 > 10 mu M). (C) 2012 Elsevier Ltd. All rights reserved.
• US8461329B2
  申请人：——

  公开号：US8461329B2

  公开（公告）日：2013-06-11