methyl 5-acetyl-2-chlorobenzoate | 792911-92-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-acetyl-2-chlorobenzoate
• 英文别名: 5-acetyl-2-chloro-benzoic acid methyl ester
• CAS: 792911-92-3
• 化学式: C₁₀H₉ClO₃
• 分子量: 212.633
• InChiKey: YMIRUDJJFHTLRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-acetyl-2-chlorobenzoate 在 溴 、 三氟乙酸 作用下， 反应 2.0h， 生成 5-(2-bromo-acetyl)-2-chloro-benzoic acid methyl ester
  参考文献：
  名称：

  [EN] BENZAMIDE INHIBITORS OF THE P2X7 RECEPTOR
  [FR] INHIBITEURS BENZAMIDIQUES DU RECEPTEUR P2X7

  摘要：

  本发明提供了P2X7受体的苯甲酰胺抑制剂，其化学式为(I)，其中R1-R3如本文所定义。本发明的化合物在治疗IL-1介导的疾病方面具有用途，包括但不限于炎症性疾病，如骨关节炎和类风湿关节炎；过敏，哮喘，慢性阻塞性肺病，癌症，再灌注或缺血性中风或心脏病发作，自身免疫疾病和其他疾病。

  公开号：

  WO2004099146A1
• 作为产物：
  描述：

  2-氯-5-溴苯甲酸甲酯 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 三乙胺 、 三苯基膦 作用下， 生成 methyl 5-acetyl-2-chlorobenzoate
  参考文献：
  名称：

  Discovery, synthesis and SAR of azinyl- and azolylbenzamides antagonists of the P2X7 receptor

  摘要：

  The discovery, of a series of 2-Cl-5-heteroaryl-benzamide antagonists of the P2X(7) receptor via parallel medicinal chemistry is described. Initial analogs suffered from poor metabolic stability and low Vd(ss). Multi parametric optimization led to identification of pyrazole 39 as a viable lead with excellent potency and oral bioavailability. Further attempts to improve the low Vd(ss) of 39 via introduction of amines led to analogs 40 and 41 which maintained the favorable pharmacology profile of 39 and improved Vd(ss) after iv dosing. But these analogs suffered from poor oral absorption, probably driven by poor permeability. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.117

文献信息

• [EN] PHTALAZINONE DERIVATIVES AS MPEGS -1 INHIBITORS<br/>[FR] DÉRIVÉS DE PHTALAZINONE EN TANT QU'INHIBITEURS DE MPGES-1
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2013072825A1

  公开（公告）日：2013-05-23

  The present patent application is directed to bicyclic compounds of formula (I) or pharmaceutically acceptable salt thereof as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (m PGES-1) enzyme and are therefore useful in the treatment of pain and/or inflammation from a variety of diseases or conditions, such as asthma, osteoarthritis, rheumatoid arthritis, acute or chronic pain and neurodegenerative diseases.

  本专利申请涉及公式(I)的双环化合物或其药用盐，作为mPGES-1抑制剂。这些化合物是微粒体前列腺素E合成酶-1（mPGES-1）酶的抑制剂，因此在治疗多种疾病或情况引起的疼痛和/或炎症方面非常有用，如哮喘、骨关节炎、类风湿性关节炎、急性或慢性疼痛和神经退行性疾病。
• Identification of Eukaryotic Translation Elongation Factor 1-α 1 Gamendazole-Binding Site for Binding of 3-Hydroxy-4(1<i>H</i>)-quinolinones as Novel Ligands with Anticancer Activity
  作者：Kristyna Burglová、Gabriela Rylová、Athanasios Markos、Hana Prichystalova、Miroslav Soural、Marek Petracek、Martina Medvedikova、Gracian Tejral、Bruno Sopko、Pavel Hradil、Petr Dzubak、Marian Hajduch、Jan Hlavac

  DOI：10.1021/acs.jmedchem.8b00078

  日期：2018.4.12

  modeling. The drug was previously described as a ligand for eukaryotic translation elongation factor 1-α 1 (eEF1A1) and found to be a potential target site for derivatives of 2-phenyl-3-hydroxy-4(1H)-quinolinones (3-HQs), which exhibit anticancer activity. The interaction of this class of derivatives of 3-HQs with eEF1A1 inside cancer cells was confirmed via pull-down assay. We designed and synthesized

  在这里，我们使用计算模型确定了避孕药Gamendazole的相互作用部位。该药物先前被描述为真核翻译延伸因子1-α1（eEF1A1）的配体，被发现是2-苯基-3-羟基-4（1 H）-喹啉酮（3-HQs）衍生物的潜在靶位），具有抗癌活性。通过下拉测定法证实了这类3-HQs衍生物与癌细胞内eEF1A1的相互作用。我们设计并合成了一个新的3-HQ家族，随后应用了等温滴定量热法，表明这些化合物与eEF1A1牢固结合。此外，我们发现这些衍生物中的一些具有显着的体外抗癌活性。
• Benzamide inhibitors of the P2X7 receptor
  申请人：Dombroski A. Mark

  公开号：US20050009900A1

  公开（公告）日：2005-01-13

  The present invention provides benzamide inhibitors of the P2X 7 receptor of the formula: wherein R 1 -R 3 are as defined herein. The compounds of the invention are useful in the treatment of IL-1 mediated disorders, including, without limitation, inflammatory diseases such as osteoarthritis and rheumatoid arthritis; allergies, asthma, COPD, cancer, reperfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.

  本发明提供了公式如下的P2X7受体的苯甲酰胺抑制剂：其中R1-R3如本文所定义。本发明的化合物在治疗IL-1介导的疾病方面具有用处，包括但不限于炎症性疾病，如骨关节炎和类风湿性关节炎；过敏、哮喘、慢性阻塞性肺疾病、癌症、中风或心脏病发作中的再灌注或缺血、自身免疫性疾病和其他疾病。
• Benzamide Inhibitors of the P2X7 Receptor
  申请人：Dombroski A. Mark

  公开号：US20070142329A1

  公开（公告）日：2007-06-21

  The present invention provides benzamide inhibitors of the P2X 7 receptor of the formula: wherein R 1 -R 3 are as defined herein. The compounds of the invention are useful in the treatment of IL-1 mediated disorders, including, without limitation, inflammatory diseases such as osteoarthritis and rheumatoid arthritis; allergies, asthma, COPD, cancer, reperfusion or ischemia in stroke or heart attack, autoimmune diseases and other disorders.

  本发明提供了P2X7受体的苯甲酰胺抑制剂，其化学式如下：其中R1-R3的定义如本文所述。本发明中的化合物可用于治疗IL-1介导的疾病，包括但不限于炎症性疾病，如骨关节炎和类风湿性关节炎；过敏、哮喘、COPD、癌症、脑卒中或心脏病发作中的再灌注或缺血、自身免疫疾病和其他疾病。
• BENZAMIDE INHIBITORS OF THE P2X7 RECEPTOR
  申请人：Pfizer Products Inc.

  公开号：EP1626962A1

  公开（公告）日：2006-02-22