2,3-diphenylquinoline-4-carboxylic acid | 99686-98-3

• 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: 2,3-diphenylquinoline-4-carboxylic acid
• 英文别名: 2,3-diphenyl-quinoline-4-carboxylic acid；2,3-Diphenyl-chinolin-4-carbonsaeure；3-Phenylcinchophen
• CAS: 99686-98-3
• 化学式: C₂₂H₁₅NO₂
• 分子量: 325.367
• InChiKey: ZBKJWKHDYQZPFG-UHFFFAOYSA-N

物化性质

• 沸点：
  459.5±33.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• 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：

  2,3-diphenylquinoline-4-carboxylic acid 在 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 2,3-diphenyl-quinoline-4-carbonyl chloride
  参考文献：
  名称：

  一些 2-Aryl- 和 2,3-Diaryl-quinolin-4- 羧酸衍生物的合成

  摘要：

  摘要 合成了十八种2-芳基-和2,3-二芳基-喹啉-4-羧酸衍生物。基本上，这些化合物的合成设计源于目标化合物的适当断开，这表明丙酮酸、芳香胺和苯甲醛或苯基丙酮酸、芳香胺和苯甲醛是 2-芳基-和 2 的可能逻辑前体，分别为 3-芳基-喹啉-4-羧酸。通过色谱和光谱技术（紫外、红外、质谱、1H NMR 和 13C NMR）阐明合成化合物的纯度和特性。筛选制备的衍生物对标准细菌生物体枯草芽孢杆菌、金黄色葡萄球菌、大肠杆菌和普通假单胞菌的抗菌活性。2、

  DOI：

  10.1080/00397911.2010.486508
• 作为产物：
  描述：

  2-碘乙酰苯胺 在 氢氧化钾 、 PdCl2(PMePh2)2 作用下， 40.0 ℃ 、5.27 MPa 条件下， 反应 66.0h， 生成 2,3-diphenylquinoline-4-carboxylic acid
  参考文献：
  名称：

  Palladium-catalyzed double carbonylation of aryl halides affording .alpha.-keto amides. Applications to synthesis of isatin and quinoline derivatives

  摘要：

  DOI：

  10.1021/jo00353a033

文献信息

• Discovery of a Novel Class of Selective Non-Peptide Antagonists for the Human Neurokinin-3 Receptor. 2. Identification of (<i>S</i>)-<i>N</i>-(1-Phenylpropyl)-3-hydroxy-2- phenylquinoline-4-carboxamide (SB 223412)
  作者：Giuseppe A. M. Giardina、Luca F. Raveglia、Mario Grugni、Henry M. Sarau、Carlo Farina、Andrew D. Medhurst、Davide Graziani、Dulcie B. Schmidt、Roberto Rigolio、Mark Luttmann、Stefano Cavagnera、James J. Foley、Vittorio Vecchietti、Douglas W. P. Hay

  DOI：10.1021/jm980633c

  日期：1999.3.1

  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.
• α-(2-Piperidyl)-2-aryl-4-quinolinemethanols¹
  作者：Ronald F. Brown、Thomas L. Jacobs、S. Winstein、Milton C. Kloetzel、Earl C. Spaeth、Warner H. Florsheim、John H. Robson、Edward F. Levy、George M. Bryan、Alan B. Magnusson、Stanley J. Miller、Melvin L. Ott、Joseph A. Terek

  DOI：10.1021/ja01216a087

  日期：1946.12
• Borsche; Vorbach, Justus Liebigs Annalen der Chemie, 1939, vol. 537, p. 22,36
  作者：Borsche、Vorbach

  DOI：——

  日期：——
• Unilaterally acylated diamines and process of making same
  申请人：SOC OF CHEMICAL IND

  公开号：US01886481A1

  公开（公告）日：1932-11-08
• DE540697
  申请人：——

  公开号：——

  公开（公告）日：——