Ethyl 10-hydroxy-2,3-diphenyl-pyrido[3,2-f]quinoxaline-9-carboxylate | 174623-03-1

• 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: Ethyl 10-hydroxy-2,3-diphenyl-pyrido[3,2-f]quinoxaline-9-carboxylate
• 英文别名: ethyl 10-oxo-2,3-diphenyl-7H-pyrido[3,2-f]quinoxaline-9-carboxylate
• CAS: 174623-03-1
• 化学式: C₂₆H₁₉N₃O₃
• 分子量: 421.455
• InChiKey: BEOXUFMCXRJKOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 10-hydroxy-2,3-diphenyl-pyrido[3,2-f]quinoxaline-9-carboxylate 在 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 7-(4-(trifluoromethyl)benzyl)-10-oxo-2,3-diphenyl-7,10-dihydropyrido[3,2-f]quinoxaline-9-carboxylic acid
  参考文献：
  名称：

  Emergence of pyrido quinoxalines as new family of antimalarial agents

  摘要：

  A series of novel N-alkyl dihydro pyrido quinoxaline derivatives were synthesized using Gould-Jacobs reaction and evaluated their antimalarial activity in vitro against chloroquine sensitive (3D7) and drug resistant (Dd2) strains of Plasmodium falciparum. Among the compounds tested, 10 compounds were more potent than their structural standard analog ciprofloxacin, including 2 derivatives 5e and 5h, which showed 3.3-7.4 times more potency than ciprofloxacin against both the parasite strains. The results are encouraging and a lead molecule may emerge which is useful alone or in combination therapy. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.010
• 作为产物：
  描述：

  6-nitro-2,3-diphenylquinoxaline 在 palladium 10% on activated carbon 、 一水合肼 作用下， 以 二苯醚 、 乙醇 为溶剂， 反应 6.0h， 生成 Ethyl 10-hydroxy-2,3-diphenyl-pyrido[3,2-f]quinoxaline-9-carboxylate
  参考文献：
  名称：

  Emergence of pyrido quinoxalines as new family of antimalarial agents

  摘要：

  A series of novel N-alkyl dihydro pyrido quinoxaline derivatives were synthesized using Gould-Jacobs reaction and evaluated their antimalarial activity in vitro against chloroquine sensitive (3D7) and drug resistant (Dd2) strains of Plasmodium falciparum. Among the compounds tested, 10 compounds were more potent than their structural standard analog ciprofloxacin, including 2 derivatives 5e and 5h, which showed 3.3-7.4 times more potency than ciprofloxacin against both the parasite strains. The results are encouraging and a lead molecule may emerge which is useful alone or in combination therapy. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.010

文献信息

• Venugopalan, B.; Souza, E. Pinto de; Sathe, K. M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 9, p. 778 - 790
  作者：Venugopalan, B.、Souza, E. Pinto de、Sathe, K. M.、Chatterjee, D. K.、Iyer, N.

  DOI：——

  日期：——
• Gould-Jacobs reaction of 6-amino-2,3-diphenylquinoxaline
  作者：V. Milata、D. Ilavsky、M. Chudík、Ľ. Zalibera、J. Leško、M. Seman、A. Belicova

  DOI：10.1007/bf00807064

  日期：1995.12

  Catalytic hydrogenation of 2,3-diphenyl-6-nitroquinoxaline led to the corresponding amine 1 which in turn afforded products 3a-i on reaction with alkoxymethylene derivatives 2a-i. Thermal cyclization of 3b and 3f yielded substituted pyrazinoquinolones 5b and 5f, respectively. Optimal conditions for the successful hydrolysis of ester 5b were found. The structures of all products were deduced from their IR, UV, H-1, and C-13 NMR spectroscopic data.