11-methyl-diindeno[1,2-b;2',1'-e]pyridine-10,12-dione | 98655-78-8

• 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: 11-methyl-diindeno[1,2-b;2',1'-e]pyridine-10,12-dione
• 英文别名: 11-Methyl-diindeno[1,2-b;2',1'-e]pyridin-10,12-dion
• CAS: 98655-78-8
• 化学式: C₂₀H₁₁NO₂
• 分子量: 297.313
• InChiKey: XBAHZPYVIQBVNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  47.03
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  11-methyl-diindeno[1,2-b;2',1'-e]pyridine-10,12-dione 在 磷化氢 、 氢碘酸 作用下， 生成 11-methyl-10,12-dihydrodiindeno<1,2-b:2,1-e>pyridine
  参考文献：
  名称：

  Chatterjea; Prasad, Journal Of Scientific and Industrial Research, 1955, vol. 14 B, p. 383,388

  摘要：

  DOI：
• 作为产物：
  描述：

  4-methyl-2,6-diphenyl-pyridine-3,5-dicarboxylic acid diethyl ester 在 氢氧化钾 、 三氯化铝 、 氯化亚砜 、 硝基苯 作用下， 生成 11-methyl-diindeno[1,2-b;2',1'-e]pyridine-10,12-dione
  参考文献：
  名称：

  Chatterjea; Prasad, Journal Of Scientific and Industrial Research, 1955, vol. 14 B, p. 383,388

  摘要：

  DOI：

文献信息

• Synthesis, cytotoxicity, QSAR, and intercalation study of new diindenopyridine derivatives
  作者：Ramin Miri、Katayoun Javidnia、Bahram Hemmateenejad、Ali Azarpira、Zahra Amirghofran

  DOI：10.1016/j.bmc.2004.03.032

  日期：2004.5

  Seven new derivatives of diindenopyridine were synthesized by Hantsch pyridine synthesis. Their biological activity to inhibit cell proliferation was assessed by MTT assay on seven cell lines. 11-(4-Fluoro-phenyl)-diindeno[1,2-b;2',1'-e]pyridine-10,12-dione and 11-(2-nitro-phenyl)-diindeno[1,2-b;,2',1'-e]pyridine-10,12-dione were active on K-562 cell line with IC50 values of 79.66 and 78.2 muM, respectively. Effect of structural parameters on the cytotoxicity was evaluated by quantitative structure activity relationship (QSAR) analysis and a linear relationship was found between the -log IC15 of these compounds and their Surface area and molar refractivity. To model the DNA-intercalator complex, force field molecular mechanic calculation was employed and the binding energy of the reaction between the intercalating agent and each reasonable double base pairs of DNA was calculated. It was found that these molecules could intercalate into the DNA. Also, it was observed that 11-(2-nitro-phenyl)-diindeno[1,2-b;2',1'-e]pyridine-10,12-dione. which showed the highest activity in K-562 cell line, produced the most negative binding energy with a moderate selectivity toward A-G/T-C double base pairs. (C) 2004 Elsevier Ltd. All rights reserved.