6-(4-(pyrimidin-2-yl)piperazin-1-yl)phenanthridine | 1577289-34-9

• 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: 6-(4-(pyrimidin-2-yl)piperazin-1-yl)phenanthridine
• 英文别名: 6-(4-Pyrimidin-2-ylpiperazin-1-yl)phenanthridine；6-(4-pyrimidin-2-ylpiperazin-1-yl)phenanthridine
• CAS: 1577289-34-9
• 化学式: C₂₁H₁₉N₅
• 分子量: 341.415
• InChiKey: YFWMJZPRKNMTER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  45.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  6(5H)-菲啶酮 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-(4-(pyrimidin-2-yl)piperazin-1-yl)phenanthridine
  参考文献：
  名称：

  使用 DMF 作为 C1 源的 2-芳基苯胺的环境温度脱氢 C(Ar)–H 羰基内酰胺化

  摘要：

  报道了由可见光和钾碱促进的 2-芳基苯胺的直接脱氢 C-H 裂解羰基内酰胺化。在没有氧化剂的情况下，溶剂 DMF 充当唯一的羰基来源。氢气的不可逆释放将此反应拖向稳定的菲啶酮产物。这项工作提供了将广泛的 2-芳基苯胺直接转化为各种菲啶酮的方法。该方法可应用于生物活性分子和有机光电材料的合成。

  DOI：

  10.1021/acs.orglett.3c00585

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.
• Ambient Temperature Dehydrogenative C(Ar)–H Carbonylative Lactamization of 2-Arylanilines Using DMF as C1-Source
  作者：Yong-Ze Chen、Ting-Hui Ding、Qiang-Qiang Li、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.orglett.3c00585

  日期：2023.4.21

  dehydrogenative C–H cleaving carbonylative lactamization of 2-arylanilines promoted by visible light and potassium bases is reported. Solvent DMF acts as the sole carbonyl source in the absence of an oxidant. The irreversible release of hydrogen gas drags this reaction to the stable phenanthridinone products. This work provides a direct conversion of a broad range of 2-arylanilines to various phenanthridinones.

  报道了由可见光和钾碱促进的 2-芳基苯胺的直接脱氢 C-H 裂解羰基内酰胺化。在没有氧化剂的情况下，溶剂 DMF 充当唯一的羰基来源。氢气的不可逆释放将此反应拖向稳定的菲啶酮产物。这项工作提供了将广泛的 2-芳基苯胺直接转化为各种菲啶酮的方法。该方法可应用于生物活性分子和有机光电材料的合成。