(3E)-N2-(2-((4-chlorobenzylidene)amino)phenyl)-N3-phenyl-1,4-dihydroquinoxaline-2,3-diimine | 1352920-40-1

• 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: (3E)-N2-(2-((4-chlorobenzylidene)amino)phenyl)-N3-phenyl-1,4-dihydroquinoxaline-2,3-diimine
• CAS: 1352920-40-1
• 化学式: C₂₇H₂₀ClN₅
• 分子量: 449.942
• InChiKey: GNGUEJGKHVKGDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.66
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3E)-N2-(2-((4-chlorobenzylidene)amino)phenyl)-N3-phenyl-1,4-dihydroquinoxaline-2,3-diimine 、 氯乙酰氯 在 三乙胺 作用下， 以 二恶烷 为溶剂， 以70.2%的产率得到3-choro-4-(4-chorophenyl)-1-(2-((E)-((E)-3-(phenylimino)-3,4-dihydroquinoxalin-2-(1H)-ylidene)amino)phenyl)azetidin-2-one
  参考文献：
  名称：

  Synthesis, In Vitro Antitubercular Activity and 3D-QSAR of Novel Quinoxaline Derivatives

  摘要：

  Twenty new quinoxalines bearing azetidinone and thiazolidinone groups were synthesized by cyclocondensation of Schiff bases of quinoxaline‐2, 3‐dione and were characterized with several analytical tools. They were tested against Mycobacterium tuberculosis H37Rv at a concentration of 10 μg/mL by Microplate Alamar Blue Assay method. Quinoxaline derivatives with 2‐chloro, dimethylamino and nitro substitutions exhibited in vitro activity, comparable to that of the drug, isoniazid. Three‐dimensional quantitative structure–activity relationship studies indicated that electrostatic and steric field descriptors could explain the observed activity. The developed model fits the data well and has good predictive capability (r2 = 0.81, q2 = 0.71, F = 27.06, r2_pred = 0.84, r2 m = 0.84, r2 BS = 0.80). Electronegative groups play an important role in the antitubercular activity.

  DOI：

  10.1111/j.1747-0285.2011.01246.x
• 作为产物：
  描述：

  3-(phenylamino)quinoxalin-2(1H)-one 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.03h， 生成 (3E)-N2-(2-((4-chlorobenzylidene)amino)phenyl)-N3-phenyl-1,4-dihydroquinoxaline-2,3-diimine
  参考文献：
  名称：

  Synthesis, In Vitro Antitubercular Activity and 3D-QSAR of Novel Quinoxaline Derivatives

  摘要：

  Twenty new quinoxalines bearing azetidinone and thiazolidinone groups were synthesized by cyclocondensation of Schiff bases of quinoxaline‐2, 3‐dione and were characterized with several analytical tools. They were tested against Mycobacterium tuberculosis H37Rv at a concentration of 10 μg/mL by Microplate Alamar Blue Assay method. Quinoxaline derivatives with 2‐chloro, dimethylamino and nitro substitutions exhibited in vitro activity, comparable to that of the drug, isoniazid. Three‐dimensional quantitative structure–activity relationship studies indicated that electrostatic and steric field descriptors could explain the observed activity. The developed model fits the data well and has good predictive capability (r2 = 0.81, q2 = 0.71, F = 27.06, r2_pred = 0.84, r2 m = 0.84, r2 BS = 0.80). Electronegative groups play an important role in the antitubercular activity.

  DOI：

  10.1111/j.1747-0285.2011.01246.x