2-methyl-4-phenyl-3-quinolinecarboxylic acid | 10265-84-6

• 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-methyl-4-phenyl-3-quinolinecarboxylic acid
• 英文别名: 2-methyl-4-phenylquinoline-3-carboxylic acid
• CAS: 10265-84-6
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: XGOVHQRZEWXRBV-UHFFFAOYSA-N

物化性质

• 熔点：
  265-267 °C(Solv: acetic acid (64-19-7))
• 沸点：
  393.6±30.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-methyl-4-phenyl-3-quinolinecarboxylic acid 在 氯化亚砜 、 sodium hydride 、 三乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 N-[3,5-Bis(trifluoromethyl)benzyl]-N,2-dimethyl-4-phenyl-3-quinolinecarboxamide
  参考文献：
  名称：

  A Non-Peptide NK₁ Receptor Agonist Showing Subpicomolar Affinity

  摘要：

  3-Quinolinecarboxamides have been synthesized and evaluated for their binding to the human NK1 receptor. Several secondary amide derivatives show NK1 receptor affinity in the picomolar range. The most active compound, hydroxymethylcarboxamide 3h showing an IC50 value in the subpicomolar range, behaved as an agonist of NK1 receptor in endothelial cell proliferation, inositol phosphate turnover, and NO-mediated cyclic GMP accumulation, thus proving it to be the first non-peptide NK, receptor agonist showing very high potency.

  DOI：

  10.1021/jm034219a
• 作为产物：
  描述：

  N-{2-[bromo(phenyl)methyl]phenyl}benzenesulfonamide 在 sodium hydroxide 、 sodium hydride 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.0h， 生成 2-methyl-4-phenyl-3-quinolinecarboxylic acid
  参考文献：
  名称：

  Cremonesi, Giuseppe; Croce, Piero Dalla; Fontana, Francesco, Heterocycles, 2006, vol. 69, # 1, p. 475 - 480

  摘要：

  DOI：

文献信息

• Friedländer annulation: scope and limitations of metal salt Lewis acid catalysts in selectivity control for the synthesis of functionalised quinolines
  作者：Babita Tanwar、Dinesh Kumar、Asim Kumar、Md. Imam Ansari、Mohammad Mohsin Qadri、Maulikkumar D. Vaja、Madhulika Singh、Asit K. Chakraborti

  DOI：10.1039/c5nj02010g

  日期：——

  products during the reaction involving 2-aminobenzophenone and ethyl acetoacetate. Among a pool of metal halides, tetrafluoroborates, perchlorates, and triflates used as catalysts, In(OTf)3 emerged as the most effective catalyst for the selective/exclusive formation of the Friedländer product. The generality of the In(OTf)3-catalysed Friedländer reaction was demonstrated by the reaction of differently substituted

  检查了金属盐路易斯酸催化剂的范围和局限性，以控制在涉及2-氨基二苯甲酮和乙酰乙酸乙酯的反应过程中弗里德兰德和非​​弗里德兰德产品形成的选择性。在用作催化剂的一系列金属卤化物，四氟硼酸盐，高氯酸盐和三氟甲磺酸盐中，In（OTf）3成为选择性/排他地形成弗里德兰德产品的最有效催化剂。In（OTf）3催化的Friedländer反应的普遍性通过不同取代的2-氨基芳基酮与各种含有活性亚甲基的羰基化合物（例如，，无溶剂条件下的β-酮酸酯，环状/无环β-二酮，环状/酰基酮和芳基/杂芳基甲基酮），以75-92％的收率提供所需的喹啉。
• Poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) and N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide as efficient reagents for synthesis of quinolines
  作者：Ramin Ghorbani-Vaghei、Somayeh Akbari-Dadamahaleh

  DOI：10.1016/j.tetlet.2008.12.076

  日期：2009.3

  Poly(N-bromo-N-ethylbenzene-1,3-disulfonamide) [PBBS] and N,N,N′,N′-tetrabromobenzene-1,3-disulfonamide [TBBDA] were used as efficient reagents for the synthesis of quinolines in excellent yields from 2-aminoaryl ketones and carbonyl compounds under aqueous and solvent-free conditions.

  聚（N-溴-N-乙基苯-1,3-二磺酰胺）[PBBS]和N，N，N ' ，N'-四溴苯-1,3-二磺酰胺[TBBDA]被用作合成喹啉的有效试剂在无水和无溶剂条件下，从2-氨基芳基酮和羰基化合物可得到优异的收率。
• Mapping and Fitting the Peripheral Benzodiazepine Receptor Binding Site by Carboxamide Derivatives. Comparison of Different Approaches to Quantitative Ligand−Receptor Interaction Modeling
  作者：Maurizio Anzini、Andrea Cappelli、Salvatore Vomero、Michele Seeber、Maria Cristina Menziani、Thierry Langer、Bertram Hagen、Cristina Manzoni、Jean-Jacques Bourguignon

  DOI：10.1021/jm0009742

  日期：2001.4.1

  electrostatic contribution to the interaction (CoMFA, CoMSIA, and surface approaches) perform well, but they do not improve the quantitative models. Moreover, useful hints for the identification of the antagonist binding site in the three-dimensional modeling of the receptor (direct approach) were provided by the receptor hypothesis derived by the pharmacophoric approach. The ligand-receptor complexes

  研究与1-（2-氯苯基）-N-甲基-N-（1-甲基丙基）-3-异喹啉羧酰胺相关的外围苯并二氮杂receptor受体（PBR）配体结合位点的合成计算方法（PK11195，1）它们的受体中的内切酶（Cappelli等人，J.Med.Chem.1997，40，2910-2921）已被扩展。设计了一系列具有不同取代的平面芳族或杂芳族体系的羧酰胺衍生物，其目的是获得有关羰基和芳族部分与PBR结合位点相互作用的拓扑学要求的进一步信息。这些化合物中的大多数的合成涉及适当内酯的Weinreb酰胺化作为关键步骤。在新合成的化合物中，最有效的化合物是 图1显示了与1所示相似的纳摩尔PBR亲和力，并且在喹啉核的3位上存在碱性N-乙基-N-苄基氨基甲基。因此，可以认为它是一类新的1类水溶性衍生物的第一个例子。几种计算方法被用来提供分离的配体的描述子（间接方法），这些配体能够合理化扩大序列的结合亲和力的变化。化合物
• Synthesis and evaluation of novel triazolyl quinoline derivatives as potential antileishmanial agents
  作者：Akanksha Upadhyay、Pragati Kushwaha、Sampa Gupta、Ranga Prasad Dodda、Karthik Ramalingam、Ruchir Kant、Neena Goyal、Koneni V. Sashidhara

  DOI：10.1016/j.ejmech.2018.05.014

  日期：2018.6

  The high potential of quinoline containing natural products and their derivatives in medicinal chemistry led us to discover novel series of 25 compounds for the development of new antileishmanial agents. A series of triazolyl 2-methyl-4-phenylquinoline-3-carboxylate derivatives has been synthesized via click chemistry inspired molecular hybridization approach and evaluated against Leishmania donovani

  含喹啉的天然产物及其衍生物在药物化学中的巨大潜力使我们发现了一系列25种化合物，用于开发新的抗疟药。通过点击化学启发的分子杂交方法合成了一系列三唑基2-甲基-4-苯基喹啉-3-羧酸酯衍生物，并针对利什曼原虫进行了评估。大部分的筛选衍生物表现出显著体外抗利什曼病活性对前鞭毛体（IC 50范围从2.43到45.75μM）和胞内无鞭毛体（IC 50范围从7.06至34.9μM）比对照，米替福新（IC 50 = 8.4μM），与标准药物相比，细胞毒性较小。总体结果表明，原型标志着抗衰老化学疗法的新结构领先。
• A Non-Peptide NK₁ Receptor Agonist Showing Subpicomolar Affinity
  作者：Andrea Cappelli、Germano Giuliani、Gal.la Pericot Mohr、Andrea Gallelli、Maurizio Anzini、Salvatore Vomero、Aroldo Cupello、Simona Scarrone、Mario Matarrese、Rosa Maria Moresco、Ferruccio Fazio、Federica Finetti、Lucia Morbidelli、Marina Ziche

  DOI：10.1021/jm034219a

  日期：2004.3.1

  3-Quinolinecarboxamides have been synthesized and evaluated for their binding to the human NK1 receptor. Several secondary amide derivatives show NK1 receptor affinity in the picomolar range. The most active compound, hydroxymethylcarboxamide 3h showing an IC50 value in the subpicomolar range, behaved as an agonist of NK1 receptor in endothelial cell proliferation, inositol phosphate turnover, and NO-mediated cyclic GMP accumulation, thus proving it to be the first non-peptide NK, receptor agonist showing very high potency.