N-(2,4-dimethyl-phenyl)-2-(1H-indol-3-ylazo)benzamide | 1401521-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2,4-dimethyl-phenyl)-2-(1H-indol-3-ylazo)benzamide
• 英文别名: N-(2,4-dimethylphenyl)-2-(1H-indol-3-yldiazenyl)benzamide
• CAS: 1401521-35-4
• 化学式: C₂₃H₂₀N₄O
• 分子量: 368.438
• InChiKey: DPBVTWXYBSZZFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 在 盐酸 、 氯化亚砜 、 sodium nitrite 作用下， 以 乙醚 、 水 为溶剂， 反应 3.75h， 生成 N-(2,4-dimethyl-phenyl)-2-(1H-indol-3-ylazo)benzamide
  参考文献：
  名称：

  Synthesis, in vitro antimicrobial, antiproliferative, and QSAR studies of N-(substituted phenyl)-2/4-(1H-indol-3-ylazo)-benzamides

  摘要：

  In this study, N-(substituted phenyl)-2/4-(1H-indol-3-ylazo)-benzamides (1-26) were synthesized and screened for their in vitro antibacterial (Gram positive; S. aureus, B. subtilis and Gram negative; E. coli) and antifungal (C. albicans and A. niger) activities. The antimicrobial activity results indicated that compound, 4-(1H-indol-3-ylazo)-N-(4-nitro-phenyl)-benzamide (12, pMIC(am) = 1.61) was the most potent. In general, it was found that the synthesized compounds were bacteriostatic/fungistatic in action except fungicidal for A. niger. The synthesized compounds were also evaluated for their antiproliferative activity against human colon cancer (HCT116), murine leukemia (P388), and breast cancer (MCF7) cell lines. The antiproliferative study results demonstrated 4-(1H-indol-3-ylazo)-N-p-tolyl-benzamide (2, IC50 = 0.0003 mu M/mL) and 4-(1H-indol-3-ylazo)-N-p-tolyl-benzamide (21, 0.0003 mu M/mL) as lead compounds for the development of novel antiproliferative agents. The QSAR studies indicated the importance of topological parameters, Kier's alpha second-order shape indice (kappa I +/-(2)) and Wiener index (W) in describing the antimicrobial activity of the synthesized compounds.

  DOI：

  10.1007/s00044-012-0181-0

文献信息

• Synthesis, in vitro antimicrobial, antiproliferative, and QSAR studies of N-(substituted phenyl)-2/4-(1H-indol-3-ylazo)-benzamides
  作者：Harsh Kumar、Pradeep Kumar、Balasubramanian Narasimhan、Kalavathy Ramasamy、Vasudevan Mani、Rakesh Kumar Mishra、Abu Bakar Abdul Majeed

  DOI：10.1007/s00044-012-0181-0

  日期：2013.4

  In this study, N-(substituted phenyl)-2/4-(1H-indol-3-ylazo)-benzamides (1-26) were synthesized and screened for their in vitro antibacterial (Gram positive; S. aureus, B. subtilis and Gram negative; E. coli) and antifungal (C. albicans and A. niger) activities. The antimicrobial activity results indicated that compound, 4-(1H-indol-3-ylazo)-N-(4-nitro-phenyl)-benzamide (12, pMIC(am) = 1.61) was the most potent. In general, it was found that the synthesized compounds were bacteriostatic/fungistatic in action except fungicidal for A. niger. The synthesized compounds were also evaluated for their antiproliferative activity against human colon cancer (HCT116), murine leukemia (P388), and breast cancer (MCF7) cell lines. The antiproliferative study results demonstrated 4-(1H-indol-3-ylazo)-N-p-tolyl-benzamide (2, IC50 = 0.0003 mu M/mL) and 4-(1H-indol-3-ylazo)-N-p-tolyl-benzamide (21, 0.0003 mu M/mL) as lead compounds for the development of novel antiproliferative agents. The QSAR studies indicated the importance of topological parameters, Kier's alpha second-order shape indice (kappa I +/-(2)) and Wiener index (W) in describing the antimicrobial activity of the synthesized compounds.