1-(4-(3-(4-tolyloxy)propoxy)phenyl)-1H-pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(4-(3-(4-tolyloxy)propoxy)phenyl)-1H-pyrrole
• 英文别名: 1-[4-[3-(4-Methylphenoxy)propoxy]phenyl]pyrrole；1-[4-[3-(4-methylphenoxy)propoxy]phenyl]pyrrole
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: ADYISSYOBCZDLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(1-吡咯)苯酚 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 96.0h， 生成 1-(4-(3-(4-tolyloxy)propoxy)phenyl)-1H-pyrrole
  参考文献：
  名称：

  Discovery of target based novel pyrrolyl phenoxy derivatives as antimycobacterial agents: An in silico approach

  摘要：

  A new series of pyrrolyl phenoxy derivatives bearing alkoxy linker were synthesized and evaluated for anti-tubercular activity (anti-TB) against Mycobacterium tuberculosis. Molecular modeling, pharmacophore constructed using GALAHAD to produce an effective alignment of data set and evaluated by Pareto ranking. The pharmacophore features were filtered by Surflex-dock study using enoyl ACP reductase from M. tuberculosis, which is one of the key enzymes involved in type II fatty acid biosynthesis pathway of M. tuberculosis. Compound 6a27 showed the H-bond with NAD(+), whereas compound 6a26 showed H-bonds with Tyr158, Thr196, Met199 and NAD(+) that fitted well into the binding pocket of target InhA. The alkoxy linker bridge and acceptor groups with benzene ring were advantageous for anti-TB activity, which merit further investigation. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.013

文献信息

• Discovery of target based novel pyrrolyl phenoxy derivatives as antimycobacterial agents: An in silico approach
  作者：Uttam A. More、Shrinivas D. Joshi、Tejraj M. Aminabhavi、Venkatrao H. Kulkarni、Aravind M. Badiger、Christian Lherbet

  DOI：10.1016/j.ejmech.2015.03.013

  日期：2015.4

  A new series of pyrrolyl phenoxy derivatives bearing alkoxy linker were synthesized and evaluated for anti-tubercular activity (anti-TB) against Mycobacterium tuberculosis. Molecular modeling, pharmacophore constructed using GALAHAD to produce an effective alignment of data set and evaluated by Pareto ranking. The pharmacophore features were filtered by Surflex-dock study using enoyl ACP reductase from M. tuberculosis, which is one of the key enzymes involved in type II fatty acid biosynthesis pathway of M. tuberculosis. Compound 6a27 showed the H-bond with NAD(+), whereas compound 6a26 showed H-bonds with Tyr158, Thr196, Met199 and NAD(+) that fitted well into the binding pocket of target InhA. The alkoxy linker bridge and acceptor groups with benzene ring were advantageous for anti-TB activity, which merit further investigation. (C) 2015 Elsevier Masson SAS. All rights reserved.