喹啉-4-羧酸,2-(4-溴苯基)-6-氯- | 342017-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 喹啉-4-羧酸,2-(4-溴苯基)-6-氯-
• 英文名称: 2-(4-bromophenyl)-6-chloroquinoline-4-carboxylic acid
• CAS: 342017-94-1
• 化学式: C₁₆H₉BrClNO₂
• mdl: MFCD02319315
• 分子量: 362.61
• InChiKey: LCUJVPKQAPUUAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  喹啉-4-羧酸,2-(4-溴苯基)-6-氯- 在 氯化亚砜 、 一水合肼 作用下， 以 乙醇 、 苯 为溶剂， 反应 8.0h， 生成 2-(4-溴苯基)-6-氯喹啉-4-碳酰肼
  参考文献：
  名称：

  Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides: Synthesis and preliminary evaluation as antimicrobial agents

  摘要：

  A new series of 2-arylquinoline-4-carboxylic acid hydrazide-hydrazones was synthesized using an appropriate synthetic route. All the target compounds were evaluated for their in vitro antimicrobial activity against Staphylococcus aureus as an example for Gram-positive bacteria, Escherichia coli as an example for Gram-negative bacteria, and Candida albicans as a representative of fungi. The minimum inhibitory concentration (MIC) was determined for test compounds as well as for reference standards. Among the compounds tested, compounds having nitro substituents at the arylidene moiety showed the most potent antifungal as well as antibacterial activities against E coli. Compound 23 displayed an antifungal activity comparable to that of nystatin. However, none of the compounds demonstrated any antibacterial activity against S. aureus. Hydrophobicity of the target compounds correlated weakly with their antibacterial and antifungal activities. The most potent compounds namely, 7, 18, 19, 22, and 23 were assessed for hemolytic toxicity and found to be non-hemolytic up to a concentration of 100 mu g/mL. In addition, the most potent compound (23) was evaluated for in vitro cytotoxic activity against various cancer cell lines. This compound was found to display no cytotoxic activity but rather it induces the proliferation rate of Hep-G2 cells. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.08.022
• 作为产物：
  描述：

  N-(4-氯苯基)-2-(羟基亚胺)乙酰胺 在 硫酸 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 72.5h， 生成 喹啉-4-羧酸,2-(4-溴苯基)-6-氯-
  参考文献：
  名称：

  喹啉基STAT3小分子抑制剂的设计，合成与评价

  摘要：

  由于STAT3已被确认为抗癌靶标，因此已证明其抑制剂具有治疗人类癌症的治疗前景。为了鉴定新型和选择性的STAT3抑制剂，进行了基于STAT3 SH2结构域的虚拟筛选，以及一个小分子2-苯基喹啉-4-羧酸（5a），其抑制常数K i发现STAT3的值17.53μM。在此基础上，合成了5a的衍生物，包括酯，酰胺和二聚体。使用人乳腺癌细胞系MDA-MB-468和MCF-7测定了衍生物的生物活性和抑制选择性。在这些衍生物中，5c和9b表现出最强的抑制活性和良好的选择性，并且还抑制了MDA-MB-468细胞的STAT3蛋白水平。结果证明了虚拟筛选技术在铅发现中的成功应用。化合物9b可能是抗肿瘤药进一步开发的有效STAT3抑制剂。

  DOI：

  10.2174/1570180811310050009

文献信息

• Design, Synthesis and Molecular Docking Studies of 2-Aryl/Heteroaryl-Ethyl 6-Chloroquinoline-4-Carboxylates as Potential Antimalarial Agents
  作者：Thamatakallu O. S. Kumar、Kittappa M. Mahadevan、Pasura S. Sujanganapathy、Manikyanahally N. Kumara

  DOI：10.2174/1570180813666160722112725

  日期：2016.10.3

  In an effort to develop a lead antimalarial compounds, a series of novel 2-aryl/heteroarylethyl-6-chloroquinoline-4-carboxylate derivatives (2a-j) were obtained by using quinoline-4-carboxylic acid derivatives which were produced by a simple one-pot synthesis of Pfitzinger reaction of isatin with Arylketones as intermediates which were finally esterified with ethanol in the presence of concentrated

  为了开发抗疟疾的先导化合物，使用喹啉-4-羧酸衍生物通过简单的方法制得了一系列新的2-芳基/杂芳基乙基-6-氯喹啉-4-羧酸衍生物（2a-j）。一锅合成的伊斯廷格与芳基酮作为中间体的普菲策格反应的一锅合成法，最后在浓硫酸存在下用乙醇将其酯化，得到预期的6-氯-2-氯-2-（呋喃-2-基）喹啉-4-羧酸乙酯（2a-j）具有良好到极好的产量。通过使用硅胶（60-120目，石油醚：乙酸乙酯，9：1 v / v）的柱色谱法纯化所有粗产物，以提供分析纯的2-芳基/杂芳基-乙基-6-氯喹啉-4-羧酸盐（2a-j）。此外，产品的结构通过光谱分析（例如1H NMR， 分子对接结果表明，合成化合物中最有效的配体是2j和2h。配体乙基-2-（蒽-9-基）-6-氯喹啉-4-羧酸酯（2j）衍生物与FTase受体在活性位点氨基酸（如ARG291，LYS294）内的结合位点相互作用，结合能为-10.11 kcal /
• SAR-Based Optimization of a 4-Quinoline Carboxylic Acid Analogue with Potent Antiviral Activity
  作者：Priyabrata Das、Xiaoyi Deng、Liang Zhang、Michael G. Roth、Beatriz M. A. Fontoura、Margaret A. Phillips、Jef K. De Brabander

  DOI：10.1021/ml300464h

  日期：2013.6.13

  It is established that drugs targeting viral proteins are at risk of generating resistant strains. However, drugs targeting host factors can potentially avoid this problem. Herein, we report structure-ctivity relationship studies leading to the discovery of a very potent lead compound 6-fluoro-2-(5-isopropyl-2-methyl-4-phenoxyphenyl) quinoline -4-carboxylic acid (C44) that inhibits human dihydroorotate dehydrogenase (DHODH) with an IC50 of 1 nM and viral replication of VSV and WSN-Influenza with an EC50 of 2 nM and 41 nM. We also solved the X-ray structure of human DHODH bound to C44, providing structural insight into the potent inhibition of biaryl ether analogues of brequinar.
• A series of quinoline analogues as potent inhibitors of C. albicans prolyl tRNA synthetase
  作者：Xiang Y. Yu、Jason M. Hill、Guixue Yu、Yifeng Yang、Arthur F. Kluge、Dennis Keith、John Finn、Paul Gallant、Jared Silverman、Audrey Lim

  DOI：10.1016/s0960-894x(00)00697-1

  日期：2001.2

  A series of quinoline inhibitors of C. albicans prolyl tRNA synthetase was identified. The most potent analogue, 2-(4-bromo-phenyl)-6-chloro-8-methyl-4-quinolinecarboxylic acid, showed IC50 = 5 nM (Ca. ProRS) with high selectivity over the human enzyme. (C) 2001 Elsevier Science Ltd. All rights reserved.
• INHIBITION OF TRNA SYNTHETASES AND THERAPEUTIC APPLICATIONS THEREOF
  申请人：Whitman Malcolm

  公开号：US20120058133A1

  公开（公告）日：2012-03-08

  The present invention provides novel methods for modulating Th 17-mediated immune responses using aminoacyl tRNA synthetase inhibitors. Inhibition of aminoacyl tRNA synthetase inhibitors activates an amino acid starvation response (AAR) and can produce beneficial therapeutic effects. In some embodiments, aminoacyl tRNA synthetase inhibitors are used to treat disorders such as autoimmune diseases, graft rejection, infections, fibrosis, and inflammatory diseases.