2-(3,4-二氯苯基)-喹啉-4-羧酸 | 148887-61-0

• 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: 2-(3,4-二氯苯基)-喹啉-4-羧酸
• 中文别名: 喹啉-4-羧酸,2-(3,4-二氯苯基)-
• 英文名称: 2-(3,4-dichlorophenyl)quinoline-4-carboxylic acid
• 英文别名: 2-(3,4-dichloro-phenyl)-quinoline-4-carboxylic acid；2-(3,4-Dichlor-phenyl)-chinolin-4-carbonsaeure；2-(3,4-dichlorophenyl)-quinoline-4-carboxylic acid
• CAS: 148887-61-0
• 化学式: C₁₆H₉Cl₂NO₂
• mdl: MFCD01414694
• 分子量: 318.159
• InChiKey: METUEFNOMUIMQR-UHFFFAOYSA-N

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：

  2-(3,4-二氯苯基)-喹啉-4-羧酸 在 劳森试剂 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 7.0h， 生成 {[2-(3,4-Dichloro-phenyl)-quinoline-4-carbothioyl]-methyl-amino}-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis and aldose reductase inhibitory activity of N-(quinolinyl thiocarbonyl) glycine derivatives

  摘要：

  The onset of diabetic complications may be prevented by the inhibition of aldose reductase. Derivatives of N-(quinolinyl thiocarbonyl) glycine were prepared and their in vitro and ex vivo aldose reductase inhibitory activities were tested on rat lens. The cincophen derivatives were the most potent in vitro with an enzyme inhibition value of 29% at 10(-8) M and 91% at 10(-7) M for the N-[(2-phenylquinolin-4-yl)thiocarbonyl]-N-methylglycine compound 10a This activity was shown to be dependent on the nature of the substituents and seems to be optimal for the acids; esters were found to be inactive. No compound have shown ex vivo inhibitory activity. It is concluded that the lack of ex vivo activity is likely due to a poor bioavailability or a bad penetration of the compounds in target tissue (lens).

  DOI：

  10.1016/0223-5234(92)90032-v
• 作为产物：
  描述：

  2-羟基亚氨基-n-苯乙酰胺 在 硫酸 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 2-(3,4-二氯苯基)-喹啉-4-羧酸
  参考文献：
  名称：

  Design, synthesis and antitumour activity of bisquinoline derivatives connected by 4-oxy-3-fluoroaniline moiety

  摘要：

  A series of novel bisquinoline derivatives connected by a 4-oxy-3-fluoroaniline moiety were synthesized and evaluated for their in vitro antitumour activities against a panel of five cancer cell lines (H460, HT-29, MKN-45, U87MG, and SMMC-7721). Most of compounds tested showed a potent activity and high selectivity towards the H460 and MKN-45 cell lines. Among the compounds tested, six (15d, 15e, 15m, 15n, 16a, and 16i) were further examined for their c-Met kinase activity; the compounds showed high efficacy with IC50 values in the single-digit nM range. An analysis of structure activity relationships indicated that an unsubstituted or a halogen-substituted phenyl ring on the 2-arylquinoline-4-carboxamide moiety was favourable for antitumour activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.001

文献信息

• Application of a Parallel Synthetic Strategy in the Discovery of Biaryl Acyl Sulfonamides as Efficient and Selective Na_V1.7 Inhibitors
  作者：Erin F. DiMauro、Stephen Altmann、Loren M. Berry、Howard Bregman、Nagasree Chakka、Margaret Chu-Moyer、Elma Feric Bojic、Robert S. Foti、Robert Fremeau、Hua Gao、Hakan Gunaydin、Angel Guzman-Perez、Brian E. Hall、Hongbing Huang、Michael Jarosh、Thomas Kornecook、Josie Lee、Joseph Ligutti、Dong Liu、Bryan D. Moyer、Daniel Ortuno、Paul E. Rose、Laurie B. Schenkel、Kristin Taborn、Jean Wang、Yan Wang、Violeta Yu、Matthew M. Weiss

  DOI：10.1021/acs.jmedchem.6b00425

  日期：2016.9.8

  a parallel synthetic approach was applied to rapidly generate the derived acyl sulfonamides. A biaryl acyl sulfonamide hit from this library was elaborated, optimizing for potency and selectivity with attention to physicochemical properties. The resulting novel leads are potent, ligand and lipophilic efficient, and selective over hNaV1.5. Representative lead 36 demonstrates selectivity over other human

  大多数有效的和选择性的hNa V 1.7抑制剂具有常见的药理学特征，包括杂芳基磺酰胺头基和亲脂性芳族尾基。最近，已经出现了类似的芳香族尾基与酰基磺酰胺头基结合的报道，酰基磺酰胺赋予了相对于hNa V的选择性水平1.5与杂芳基磺酰胺相当。从满足亲脂性尾部中选定药理学要求的市售羧酸开始，采用平行合成方法快速生成衍生的酰基磺酰胺。精心制作了该文库中的联芳基酰基磺酰胺，优化了效价和选择性，并关注了理化性质。所得的新的铅是有效的，配体和亲脂性的，并且在hNa V 1.5上具有选择性。代表性的铅36证明了在鼠类中对其他人类Na V同工型的选择性和良好的药代动力学。与已知的杂芳基磺酰胺抑制剂相比，本文报道的联芳基酰基磺酰胺还可以提供ADME优势。
• NOVEL PHENYL-QUINOLINE-CARBOXYLIC ACID PYRIDINE DERIVATIVES USEFUL AS MODULATORS OF NICOTINIC ACETYLCHOLINE RECEPTORS
  申请人：Nardi Antonio

  公开号：US20110207773A1

  公开（公告）日：2011-08-25

  This invention relates to novel phenyl-quinoline-carboxylic acid pyridine derivatives, which are found to be modulators of the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.

  这项发明涉及新型苯基-喹啉-羧酸吡啶衍生物，发现它们是尼古丁型乙酰胆碱受体的调节剂。由于它们的药理特性，本发明的化合物可能对治疗与中枢神经系统（CNS）的胆碱系统、外周神经系统（PNS）、平滑肌收缩、内分泌疾病或紊乱、神经退行性疾病、炎症、疼痛以及化学物质滥用终止引起的戒断症状等多种疾病或紊乱具有用处。
• [EN] NOVEL PHENYL-QUINOLINE-CARBOXYLIC ACID PYRIDINE DERIVATIVES USEFUL AS MODULATORS OF NICOTINIC ACETYLCHOLINE RECEPTORS<br/>[FR] NOUVEAUX DÉRIVÉS DE PHÉNYLQUINOLÉINE-ACIDE CARBOXYLIQUE-PYRIDINE UTILES COMME MODULATEURS DES RÉCEPTEURS NICOTINIQUES À L'ACÉTYLCHOLINE
  申请人：NEUROSEARCH AS

  公开号：WO2010020672A1

  公开（公告）日：2010-02-25

  This invention relates to novel phenyl-quinoline-carboxylic acid pyridine derivatives, which are found to be modulators of the nicotinic acetylcholine receptors. Due to their pharmacological profile the compounds of the invention may be useful for the treatment of diseases or disorders as diverse as those related to the cholinergic system of the central nervous system (CNS), the peripheral nervous system (PNS), diseases or disorders related to smooth muscle contraction, endocrine diseases or disorders, diseases or disorders related to neuro-degeneration, diseases or disorders related to inflammation, pain, and withdrawal symptoms caused by the termination of abuse of chemical substances.

  本发明涉及新型苯基-喹啉-羧酸吡啶衍生物，发现它们是乙酰胆碱受体的调节剂。由于它们的药理特性，本发明的化合物可能对治疗与中枢神经系统（CNS）和外周神经系统（PNS）的胆碱能系统有关的疾病或障碍，平滑肌收缩有关的疾病或障碍，内分泌疾病或障碍，神经退行性疾病或障碍，炎症、疼痛以及由于化学物质滥用终止引起的戒断症状可能有用。
• The Pfitzinger Reaction in the Synthesis of Quinoline Derivatives
  作者：Ng. Ph. Buu-Hoi、R. Royer、Ng. D. Xuong、P. Jacquignon

  DOI：10.1021/jo50015a019

  日期：1953.9
• Antimalarials. 7-Chloro-4-hydroxy- and 4,7-Dichloro-1-methylcarbostyrils¹
  作者：Robert E. Lutz、John F. Codington、Russell J. Rowlett、Adolf J. Deinet、Philip S. Bailey

  DOI：10.1021/ja01213a041

  日期：1946.9