3-[4-(phenanthridin-6-yl)piperazin-1-yl]phenol | 1577289-36-1

• 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: 3-[4-(phenanthridin-6-yl)piperazin-1-yl]phenol
• 英文别名: 3-(4-Phenanthridin-6-ylpiperazin-1-yl)phenol；3-(4-phenanthridin-6-ylpiperazin-1-yl)phenol
• CAS: 1577289-36-1
• 化学式: C₂₃H₂₁N₃O
• 分子量: 355.439
• InChiKey: UCXQUJXMAIQIMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6(5H)-菲啶酮 在 N,N-二甲基苯胺 、 三乙胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 3-[4-(phenanthridin-6-yl)piperazin-1-yl]phenol
  参考文献：
  名称：

  Synthesis and evaluation of anti-tubercular activity of 6-(4-substitutedpiperazin-1-yl) phenanthridine analogues

  摘要：

  A series of seventeen new 6-(4-substitutedpiperazin-1-yl)phenanthridine derivatives were designed, synthesized, and evaluated for their anti-tubercular activity against Mycobacterium tuberculosis H(37)Rv by Microplate Alamar Blue Assay and most active compounds were tested for cytotoxicity studies against mouse macrophage cell lines (RAW264.7). Among the tested compounds, ten compounds exhibited significant activity against the growth of M. tuberculosis (MIC ranging from 1.56 to 6.25 mu g/mL). In particular, compounds 5e, 5j and 5k displayed excellent activity against the growth of M. tuberculosis (MIC 1.56 mu g/mL). The selectivity index values were found to be > 25, indicating compounds likeliness in drug development for tuberculosis. The structure of 5k is substantiated by X-ray crystallographic study. Structure activity correlation indicates the importance of substituent at 4th position of piperazinyl phenanthridine ring. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.005

文献信息

• Synthesis and evaluation of anti-tubercular activity of 6-(4-substitutedpiperazin-1-yl) phenanthridine analogues
  作者：Hunsur Nagendra Nagesh、Narva Suresh、Kalaga Mahalakshmi Naidu、Boyineni Arun、Jonnalagadda Padma Sridevi、Dharmarajan Sriram、Perumal Yogeeswari、Kondapalli Venkata Gowri Chandra Sekhar

  DOI：10.1016/j.ejmech.2014.01.005

  日期：2014.3

  A series of seventeen new 6-(4-substitutedpiperazin-1-yl)phenanthridine derivatives were designed, synthesized, and evaluated for their anti-tubercular activity against Mycobacterium tuberculosis H(37)Rv by Microplate Alamar Blue Assay and most active compounds were tested for cytotoxicity studies against mouse macrophage cell lines (RAW264.7). Among the tested compounds, ten compounds exhibited significant activity against the growth of M. tuberculosis (MIC ranging from 1.56 to 6.25 mu g/mL). In particular, compounds 5e, 5j and 5k displayed excellent activity against the growth of M. tuberculosis (MIC 1.56 mu g/mL). The selectivity index values were found to be > 25, indicating compounds likeliness in drug development for tuberculosis. The structure of 5k is substantiated by X-ray crystallographic study. Structure activity correlation indicates the importance of substituent at 4th position of piperazinyl phenanthridine ring. (C) 2014 Elsevier Masson SAS. All rights reserved.