6-氯-2-(4-氯苯基)-4-喹啉羧酸 | 126088-20-8

• 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: 6-氯-2-(4-氯苯基)-4-喹啉羧酸
• 中文别名: 6-氯-2-(4-氯苯基)-喹啉-4-羧酸；4',6-二氯2-苯基-4-喹啉羧酸
• 英文名称: 6-chloro-2-(4-chlorophenyl)quinoline-4-carboxylic acid
• 英文别名: 6-Chlor-2-(4-chlor-phenyl)-chinolin-4-carbonsaeure
• CAS: 126088-20-8
• 化学式: C₁₆H₉Cl₂NO₂
• mdl: MFCD00034813
• 分子量: 318.159
• InChiKey: ICGJQZNTTPOWLN-UHFFFAOYSA-N

物化性质

• 熔点：
  288
• 沸点：
  506.9±50.0 °C(Predicted)
• 密度：
  1.456±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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
• 危险品标志：
  Xi
• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  6-氯-2-(4-氯苯基)-4-喹啉羧酸 在 氯化亚砜 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 苯 为溶剂， 反应 8.0h， 生成 6-chloro-2-(4-chlorophenyl)quinoline-4-carboxylic acid (4-methoxybenzylidene)-hydrazide
  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：

  5-氯靛红 、 对氯苯乙酮 在 水 、 potassium hydroxide 作用下， 反应 24.0h， 生成 6-氯-2-(4-氯苯基)-4-喹啉羧酸
  参考文献：
  名称：

  Discovery of novel tubulin inhibitors targeting the colchicine binding site via virtual screening, structural optimization and antitumor evaluation

  摘要：

  The colchicine binding site of tubulin is a promising target for discovering novel antitumor agents which exert the antiangiogenic effect and are not susceptible to multidrug resistance. For identifying novel tubulin inhibitors, structure-based virtual screening was applied to identify hit 9 which displayed moderate tubulin polymerization inhibition and broad-spectrum in vitro antitumor activity. Structural optimization was performed, and biological assay revealed analog E27 displayed the best antitumor activity with IC50 values ranging from 7.81 μM to 10.36 μM, and improved tubulin polymerization inhibitory activity (IC50 = 16.1 μM). It significantly inhibited cancer cell migration and invasion, induced cell apoptosis and arrested the cell cycle at G2/M phase. Moreover, the apoptotic effect of E27 is related to the increased ROS level, the decrease of MMP, and the abnormal expression of apoptosis-related proteins. Taken together, these results suggested E27 was a promising lead compound for discovering novel tubulin-targeted antitumor agents.

  DOI：

  10.1016/j.bioorg.2021.105486

文献信息

• Acetyl-CoA carboxylase inhibitors
  申请人：Pfizer Inc.

  公开号：US20030187254A1

  公开（公告）日：2003-10-02

  Acetyl Coenzyme A Carboxylase inhibitors, pharmaceutical compositions containing such compounds and the use of such compounds to treat for example, Metabolic Syndrome including atherosclerosis, diabetes and obesity.

  乙酰辅酶A羧化酶抑制剂，含有此类化合物的药物组合物，以及使用此类化合物治疗代谢综合征，包括动脉粥样硬化、糖尿病和肥胖等疾病。
• A green synthesis of quinoline‐4‐carboxylic derivatives using <i>p</i> ‐toluenesulfonic acid as an efficient organocatalyst under microwave irradiation and their docking, molecular dynamics, ADME‐Tox and biological evaluation
  作者：Dhaval B. Patel、Dhanji P. Rajani、Smita D. Rajani、Hitesh D. Patel

  DOI：10.1002/jhet.3848

  日期：2020.4

  used for the preparation of quinoline‐4‐carboxylic acid derivatives via a one‐pot three‐component reaction of aromatic benzaldehyde, substituted aniline, and pyruvic acid under microwave irradiation. After completion of the reaction, the pure products were isolated by column chromatography. Here, to achieve the desired synthesis, various catalytic and solvent conditions were applied to perform a comparison

  P‐甲苯磺酸是一种高效，无害且可快速获得的有机催化剂，用于在微波辐射下通过芳族苯甲醛，取代的苯胺和丙酮酸的一锅三组分反应制备喹啉-4-羧酸衍生物。 。反应完成后，通过柱色谱法分离纯产物。在这里，为了实现所需的合成，应用了各种催化和溶剂条件进行比较研究。我们正在使用更高的收率，简单的后处理工艺，避免使用有害的有机溶剂，缩短反应时间以及在研究中使用本协议的更高优势。测试了合成化合物针对各种抗菌，抗真菌，抗疟和抗结核菌株的生物活性。化合物发现4a和4c（MIC 50μg/ mL）和化合物4d和4n（MIC 62.5μg/ mL）对大肠杆菌菌株具有活性，化合物4c和4p（MIC 25μg/ mL）对金黄色葡萄球菌菌株具有活性，发现化合物4c和4d对恶性疟原虫菌株具有活性。分子对接表明配体和蛋白质恰好适合结合口袋，并与生物活性显着相关。我们还测试了合成化合物的分子动力学和ADME-Tox参数。
• [EN] ACC INHIBITORS<br/>[FR] INHIBITEURS DE L'ACETYL-COA-CARBOXYLASE
  申请人：PFIZER PROD INC

  公开号：WO2003072197A1

  公开（公告）日：2003-09-04

  Acetyl Coenzyme A Carboxylase inhibitors of formula (1), pharmaceutical compositions containing such compounds and the use of such compounds to treat for example, Metabolic Syndrome including atherosclerosis, diabetes and obesity.

  Acetyl辅酶A羧化酶抑制剂的化学式（1），含有这些化合物的药物组合物以及使用这些化合物治疗代谢综合症，包括动脉粥样硬化，糖尿病和肥胖症的用途。
• Compositions and methods for modulating gated ion channels
  申请人：Babinski Kazimierz

  公开号：US20070197509A1

  公开（公告）日：2007-08-23

  The present invention relates to compositions and methods to modulate the activity of gated ion channels.

  本发明涉及用于调节门控离子通道活性的组合物和方法。
• WO2007/71055
  申请人：——

  公开号：——

  公开（公告）日：——