N-phenylquinoxaline-2-carboxamide | 37648-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-phenylquinoxaline-2-carboxamide
• 英文别名: quinoxaline-2-carboxylic acid anilide；Chinoxalin-2-carbonsaeure-anilid；Chinoxalin-carbonsaeure-(2)-anilid；2-Chinoxalincarboxanilid；N-phenyl-2-quinoxalinecarboxamide
• CAS: 37648-63-8
• 化学式: C₁₅H₁₁N₃O
• 分子量: 249.272
• InChiKey: FJPRNHHLSWRUQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 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：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenylquinoxaline-2-carboxamide 在 钯 、 溶剂黄146 作用下， 生成 1,2,3,4-tetrahydro-quinoxaline-2-carboxylic acid anilide
  参考文献：
  名称：

  Maurer; Boettger, Chemische Berichte, 1938, vol. 71, p. 1383,1390

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,2S,3R)-(2-喹喔啉基)-1,2,3,4-丁烷四醇 在 sodium hydroxide 、 氯化亚砜 、 双氧水 作用下， 生成 N-phenylquinoxaline-2-carboxamide
  参考文献：
  名称：

  Maurer; Boettger, Chemische Berichte, 1938, vol. 71, p. 1383,1390

  摘要：

  DOI：

文献信息

• Azole-<i>N</i>-Acetonitriles as Carbonyl Synthons: A One-Pot Preparation of ­Heteroaryl Amides from Halides
  作者：Tao Wang、Zhongxing Zhang、Zhiwei Yin、John F. Kadow、Nicholas A. Meanwell

  DOI：10.1055/s-2004-832849

  日期：——

  Azole-N-acetonitrile derivatives were utilized as synthons for an ambident carbonyl moiety via a strategy relying upon sequential base-mediated S N Ar substitution of a 2-halo heterocycle, in situ oxidation, and amine displacement. This strategy allows prompt and efficient synthesis of N-containing heteroaryl amides directly from the corresponding halides via a one-pot process.

  通过依赖于连续碱基介导的 SN Ar 取代 2-卤杂环、原位氧化和胺置换的策略，唑-N-乙腈衍生物被用作双基羰基部分的合成子。该策略允许通过一锅法直接从相应的卤化物快速有效地合成含 N 杂芳基酰胺。
• Synthese von chinoxalin- und indol-2,3-dicarbonsäureimiden
  作者：M. Augustin、M. Köhler、J. Faust、M.M. Al-Holly

  DOI：10.1016/0040-4020(80)80077-9

  日期：1980.1

  Quinoxaline- and indole-2,3-dicarboxyclic imides 7, 8 are prepared by reaction of halogenactive maleimides 1, 2 with sodium azide. Further derivatives of these heterocyclic series are available by secondary reactions of the imides.

  喹喔啉和吲哚-2，3-二羧酸酰亚胺7、8是通过使卤化马来酰亚胺1、2与叠氮化钠反应而制备的。这些杂环系列的其他衍生物可通过酰亚胺的二次反应获得。
• Design, synthesis and structure–activity relationship of novel quinoxalin-2-carboxamides as 5-HT3 receptor antagonists for the management of depression
  作者：Radhakrishnan Mahesh、Thangaraj Devadoss、Dilip Kumar Pandey、Shvetank Bhatt、Shushil Kumar Yadav

  DOI：10.1016/j.bmcl.2010.08.128

  日期：2010.11

  A novel series of quinoxalin-2-carboxamides were designed based on the ligand-based approach, employing a three-point pharmacophore model; it consists of an aromatic residue and a linking carbonyl group and a basic nitrogen. The target new chemical entities were synthesized from the key intermediate, quinoxalin-2-carboxylic acid, by coupling it with various amines in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC center dot HCl) and 1-hydroxybenzotriazole (HOBt). The obtained compounds' structures were confirmed by spectral data. The target new chemical entities were evaluated for their 5-HT3 receptor antagonisms in longitudinal muscle myenteric plexus preparation from guinea pig ileum against 5-HT3 agonist, 2-methyl-5-HT, which was expressed in the form of pA(2) value. All the synthesized compounds showed antagonism towards 5-HT3 receptor; based on this result, a structure-activity relationship was derived, which reveals that the aromatic residue in 5-HT3 receptor antagonists may have hydrophobic interaction with 5-HT3 receptor. Regardless of their antagonistic potentials, all the synthesized molecules were screened for their anti-depressant potentials by using forced swim test in mice model; interestingly none of the tested compounds affect the locomotion of mice in the tested dose levels. Compounds with significant pA(2) values exhibited good anti-depressant-like activity as compared to the vehicle-treated group. (C) 2010 Elsevier Ltd. All rights reserved.
• AUGUSTIN M.; KOEHLER M.; FAUST J.; AL-HOLLY M. M., TETRAHEDRON, 1980, 36, NO 12, 1801-1805
  作者：AUGUSTIN M.、 KOEHLER M.、 FAUST J.、 AL-HOLLY M. M.

  DOI：——

  日期：——
• ERHARDT H.; HUENIG S.; PUETTER H., CHEM. BER. <CHBE-AM>, 1977, 110, NO 7, 2506-2523
  作者：ERHARDT H.、 HUENIG S.、 PUETTER H.

  DOI：——

  日期：——