2-phenyl-3-bromoquinoline-4-carboxylic acid | 57464-25-2

• 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
• 英文名称: 2-phenyl-3-bromoquinoline-4-carboxylic acid
• 英文别名: 3-bromo-2-phenylquinoline-4-carboxylic acid；3-Brom-2-phenyl-chinolin-4-carbonsaeure；3-Bromocinchophene
• CAS: 57464-25-2
• 化学式: C₁₆H₁₀BrNO₂
• 分子量: 328.165
• InChiKey: RZRNLGPOSHTIJK-UHFFFAOYSA-N

物化性质

• 熔点：
  231 °C
• 沸点：
  456.7±45.0 °C(Predicted)
• 密度：
  1.556±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 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

反应信息

• 作为反应物：
  描述：

  2-phenyl-3-bromoquinoline-4-carboxylic acid 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 生成 3-Brom-cinchophenchlorid
  参考文献：
  名称：

  Discovery of a Novel Class of Selective Non-Peptide Antagonists for the Human Neurokinin-3 Receptor. 2. Identification of (S)-N-(1-Phenylpropyl)-3-hydroxy-2- phenylquinoline-4-carboxamide (SB 223412)

  摘要：

  Optimization of the previously reported 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonist 14, with regard to potential metabolic instability of the ester moiety and affinity and selectivity for the human neurokinin-3 (hNK-3) receptor, is described. The ester functionality could be successfully replaced by the ketone (31) or by lower alkyl groups (Et, 21, or n-Pr, 24). Investigation of the substitution pattern of the quinoline ring resulted in the identification of position 3 as a key position to enhance hNK-3 binding affinity and selectivity for the hNK-3 versus the hNK-2 receptor. All of the chemical groups introduced at this position, with the exception of halogens, increased the hNK-3 binding affinity, and compounds 53 (3-OH, SE 223412, hNK-3-CHO binding K-i = 1.4 nM) and 55 (3-NHz, hNK-3-CHO binding K-i = 1.2 nM) were the most potent compounds of this series. Selectivity studies versus the other neurokinin receptors (hNK-8-CHO and hNK-1-CHO) revealed that 53 is about 100-fold selective for the hNK-3 versus hNK-2 receptor, with no affinity for the hNK-1 at concentrations up to 100 mu M. In vitro studies demonstrated that 53 is a potent functional antagonist of the hNK-3 receptor (reversal of senktide-induced contractions in rabbit isolated iris sphincter muscles and reversal of NKB-induced Ca2+ mobilization in CHO cells stably expressing the hNK-3 receptor), while in vivo this compound showed oral and intravenous activity in NK-3 receptor-driven models (senktide-induced behavioral responses in mice and senktide-induced miosis in rabbits). Overall, the biological data indicate that (S)-N-(1-phenylpropyl)-3-hydroxy-2-phenylquinoline-4-carboxamide (53, SE 223412) may serve as a pharmacological tool in animal models of disease to assess the functional and pathophysiological role of the NK-3 receptor and to establish therapeutic indications for non-peptide NK-3 receptor antagonists.

  DOI：

  10.1021/jm980633c
• 作为产物：
  描述：

  2-苯基-4-喹啉羧酸 在 mercury(II) diacetate 、 溶剂黄146 作用下， 生成 2-phenyl-3-bromoquinoline-4-carboxylic acid
  参考文献：
  名称：

  Dominikiewicz, Roczniki Chemii, 1931, vol. 11, p. 664,667

  摘要：

  DOI：

文献信息

• A novel synthesis of 3-halo-2-phenylquinoline-4-carboxylic acids
  作者：Luca F. Raveglia、Giuseppe A. M. Giardina、Mario Grugni、Roberto Rigolio、Carlo Farina

  DOI：10.1002/jhet.5570340235

  日期：1997.3

  3-bromo-2-phenylquinoline-4-carboxylic acids were obtained in good yields through a novel procedure, entailing the synthesis of the 3-amino intermediate and the subsequent replacement of the amino group with chlorine or bromine, according to the Sandmeyer reaction.

  通过一种新颖的方法，以高收率获得了3-氯和3-溴-2-苯基喹啉-4-羧酸，需要合成3-氨基中间体，然后用氯或溴取代氨基。桑德迈尔反应。
• Reaction of isatin with bromo ketones under interphase-catalysis conditions
  作者：M. A. Yurovskaya、V. V. Druzhinina、Yu. G. Bundel'

  DOI：10.1007/bf00506603

  日期：1982.8
• Synthetische Versuche in der 2-Phenyl-chinolin-Reihe I. (Synthese einiger brom-substituierter 2-Phenyl-chinolin-4-karbonsäuren, Untersuchungen über die Reaktionsfähigkeit des Bromatoms in ihnen sowie Abbau von 6- und 4′- Bromatophan nach Curtius
  作者：K. Feist、M. Kuklinski

  DOI：10.1002/ardp.19362740405

  日期：——
• YUROVSKAYA, M. A.;DRUZHININA, V. V.;BUNDEL, YU. G., XIMIYA GETEROTSIKL. SOEDIN., 1982, N 8, 1130
  作者：YUROVSKAYA, M. A.、DRUZHININA, V. V.、BUNDEL, YU. G.

  DOI：——

  日期：——
• US7482458B2
  申请人：——

  公开号：US7482458B2

  公开（公告）日：2009-01-27