N-benzylquinoxaline-2-carboxamide | 7066-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-benzylquinoxaline-2-carboxamide
• 英文别名: quinoxaline-2-carboxylic acid benzylamide；Chinoxalin-2-carboxybenzylamid
• CAS: 7066-32-2
• 化学式: C₁₆H₁₃N₃O
• mdl: MFCD07675333
• 分子量: 263.299
• InChiKey: KKYVULXSLKOYID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 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：

  二碳酸二叔丁酯 、 N-benzylquinoxaline-2-carboxamide 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 生成 Benzyl-(quinoxaline-2-carbonyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  N-取代的芳香酰胺作为叔丁基酰基氨基甲酸酯的还原裂解

  摘要：

  报道了与一组杂芳族N-苄基羧酰胺，尤其是相应的叔丁基酰基氨基甲酸酯有关的合成和光谱学细节。这些化合物是研究各种杂环的假定作用所必需的（吡啶 和 吡嗪带有和不带有稠合苯环）对酰基-N键的裂解减少。所有化合物的最初特征是循环伏安法 （简历）表示各种程度的促进还原，反映了杂环成分的直接影响。研究了选择的酰基氨基甲酸酯在轻度条件下对酰基-N键的裂解作用还原剂，并通过活性铝和 硼氢化钠。转化为酰基氨基甲酸酯，然后减少 因此可能是一个温和，有效的两步程序，可实现卵裂 酰胺类，允许隔离氨基甲酸酯和 硼氢化钠 也是对应的 酒类。

  DOI：

  10.1039/b107330n
• 作为产物：
  描述：

  2-喹喔啉甲酰氯 、 苄胺 在 三乙胺 作用下， 以 苯 为溶剂， 反应 3.0h， 以70%的产率得到N-benzylquinoxaline-2-carboxamide
  参考文献：
  名称：

  Sabri, Salim S.; El-Abadelah, Mustafa M.; Al-Bitar, Bassam A., Heterocycles, 1987, vol. 26, # 3, p. 699 - 711

  摘要：

  DOI：

文献信息

• 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.
• SABRI, SALIM S.;EL-ABADELAH, MUSTAFA M.;AL-BITAR, BASSAM A., HETEROCYCLES, 26,(1987) N 3, 699-711
  作者：SABRI, SALIM S.、EL-ABADELAH, MUSTAFA M.、AL-BITAR, BASSAM A.

  DOI：——

  日期：——