1-(3-Methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)-3-(4-nitrophenyl)prop-2-en-1-one | 174136-43-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(3-Methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)-3-(4-nitrophenyl)prop-2-en-1-one
• CAS: 174136-43-7
• 化学式: C₁₈H₁₃N₃O₅
• 分子量: 351.318
• InChiKey: VICWOEASAXXUSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 乙酰甲喹 生成 1-(3-Methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)-3-(4-nitrophenyl)prop-2-en-1-one
  参考文献：
  名称：

  E-2-[3-(3,4-Dichlorophenyl)-1-oxo-2-propenyl]-3-methylquinoxaline-1,4-dioxide: A lead antitubercular agent which alters mitochondrial respiration in rat liver

  摘要：

  A series of 2-(3-aryl-1-oxo-2-propenyl)-3-methylquinoxaline-1,4-dioxides 1a-1 and 2-acetyl-3-methyl-quinoxaline-1,4-dioxide 2 were evaluated against Mycobacterium tuberculosis H(37)Rv. With the exception of the 4-nitro analog 1k, significant antitubercular potencies were observed in series 1 and 2 which have IC(50) values in the range of 1-23 mu M Negative correlations were noted between the IC(50) values of 1a-j, 1 towards M tuberculosis and both the sigma and pi constants of the substituents in the benzylidene aryl ring. In particular, 1h emerged as a lead compound having IC(50) and IC(90) figures of 1.03 mu M and 1 53 mu M, respectively. This molecule affected respiration in rat liver mitochondria which is likely one way that 1h and the bioactive analogs exert their antitubercular properties. The quinoxaline 2, which lacks an alpha,beta-unsaturated group, has no effect on mitochondrial respiration using concentrations which inhibit the growth of M. tuberculosis. (C) 2010 Elsevier Masson SAS All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.030

文献信息

• E-2-[3-(3,4-Dichlorophenyl)-1-oxo-2-propenyl]-3-methylquinoxaline-1,4-dioxide: A lead antitubercular agent which alters mitochondrial respiration in rat liver
  作者：Umashankar Das、Swagatika Das、Brian Bandy、Dennis K.J. Gorecki、Jonathan R. Dimmock

  DOI：10.1016/j.ejmech.2010.07.030

  日期：2010.10

  A series of 2-(3-aryl-1-oxo-2-propenyl)-3-methylquinoxaline-1,4-dioxides 1a-1 and 2-acetyl-3-methyl-quinoxaline-1,4-dioxide 2 were evaluated against Mycobacterium tuberculosis H(37)Rv. With the exception of the 4-nitro analog 1k, significant antitubercular potencies were observed in series 1 and 2 which have IC(50) values in the range of 1-23 mu M Negative correlations were noted between the IC(50) values of 1a-j, 1 towards M tuberculosis and both the sigma and pi constants of the substituents in the benzylidene aryl ring. In particular, 1h emerged as a lead compound having IC(50) and IC(90) figures of 1.03 mu M and 1 53 mu M, respectively. This molecule affected respiration in rat liver mitochondria which is likely one way that 1h and the bioactive analogs exert their antitubercular properties. The quinoxaline 2, which lacks an alpha,beta-unsaturated group, has no effect on mitochondrial respiration using concentrations which inhibit the growth of M. tuberculosis. (C) 2010 Elsevier Masson SAS All rights reserved.