1-(4-(2-bromoethoxy)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-(2-bromoethoxy)phenyl)-1H-pyrrole
• 英文别名: 1-[4-(2-Bromoethoxy)phenyl]pyrrole；1-[4-(2-bromoethoxy)phenyl]pyrrole
• 化学式: C₁₂H₁₂BrNO
• 分子量: 266.137
• InChiKey: DUKJTVMSAOSSOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,4-二硝基酚 、 1-(4-(2-bromoethoxy)phenyl)-1H-pyrrole 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以65%的产率得到1-(4-(2-(2,4-dinitrophenoxy)ethoxy)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
• 作为产物：
  描述：

  对氨基苯酚 在 potassium carbonate 、 potassium iodide 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 反应 56.0h， 生成 1-(4-(2-bromoethoxy)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

• [EN] 2-THIO-IMIDAZOLE DERIVATIVES AS TGR5 MODULATORS<br/>[FR] DÉRIVÉS DE 2-THIOL-IMIDAZOLE UTILES COMME MODULATEURS DE TGR5
  申请人：CADILA HEALTHCARE LTD

  公开号：WO2013054338A1

  公开（公告）日：2013-04-18

  The present invention relates to compounds of the general Formula I their pharmaceutically acceptable salts, pharmaceutically acceptable solvates, enantiomers, diastereomers, prodrugs, their N-oxide, metabolites, polymorphs, use of these compounds in medicine for treating diabetes (TGR5 modulators) and the intermediates involved in their preparation.

  本发明涉及一般式I的化合物及其药学上可接受的盐、药学上可接受的溶剂化合物、对映体、非对映体、前药、它们的N-氧化物、代谢物、多型体，在医学上用于治疗糖尿病（TGR5调节剂）以及其制备中涉及的中间体。
• 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.