6-(4-甲基哌嗪-1-基)菲啶 | 23441-13-6

• 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
• 中文名称: 6-(4-甲基哌嗪-1-基)菲啶
• 英文名称: 6-[4-methylpiperazin-1-yl]phenanthridine
• 英文别名: 6-(4-methyl-piperazyl)-phenanthridine；6-(4-methyl-piperazin-1-yl)-phenanthridine；6-(4-Methylpiperazin-1-yl)phenanthridine
• CAS: 23441-13-6
• 化学式: C₁₈H₁₉N₃
• 分子量: 277.369
• InChiKey: ZVJIBTNUNUXAIO-UHFFFAOYSA-N

物化性质

• 沸点：
  205-210 °C(Press: 0.5 Torr)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  19.4
• 氢给体数：
  0
• 氢受体数：
  3

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 6-(4-甲基哌嗪-1-基)菲啶
  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

• Novel Potent and Selective Central 5-HT₃ Receptor Ligands Provided with Different Intrinsic Efficacy. 1. Mapping the Central 5-HT₃ Receptor Binding Site by Arylpiperazine Derivatives
  作者：Andrea Cappelli、Maurizio Anzini、Salvatore Vomero、Laura Mennuni、Francesco Makovec、Edith Doucet、Michel Hamon、Giancarlo Bruni、Maria R. Romeo、M. Cristina Menziani、Pier G. De Benedetti、Thierry Langer

  DOI：10.1021/jm970645i

  日期：1998.2.1

  Synthesis and pharmacological evaluation of a series of condensed quinoline and pyridine derivatives bearing a N-methylpiperazine moiety attached to the 2-position of the quinoline or pyridine nucleus are described. 5-HT receptor binding studies revealed subnanomolar affinity for the 5-HT3 receptor subtype in some of the compounds under study. The most active compound (5b) displayed a Ki value about

  描述了一系列稠合的喹啉和吡啶衍生物的合成和药理学评价，所述稠合的喹啉和吡啶衍生物带有与喹啉或吡啶核的2-位相连的N-甲基哌嗪部分。5-HT受体结合研究表明，某些化合物对5-HT3受体亚型具有亚纳摩尔亲和力。活性最高的化合物（5b）的Ki值比喹嗪高约1个数量级，而且选择性更高。体外评估了在NG 108-15细胞中依赖5-HT3受体的[14C]胍鎓吸收情况，对四种选定化合物的潜在5-HT3激动剂/拮抗剂活性进行了评估。在此分析中，化合物5j用作5-HT3激动剂，其EC50值接近于喹嗪所报道的值，而5b是部分激动剂，其EC50值约为0.25 nM，化合物5c具有拮抗剂特性，其IC 50值（约8nM）与先前表征的5-HT 3受体拮抗剂的IC 50值在相同范围内。通过使用理论分子描述符进行的定性和定量结构亲和关系研究，可以阐明主要药效学组分的作用，并开发出一种与Quipazine相关的5-HT3配体与其受体相互作用的模型。
• Convergent Synthesis of 6-Substituted Phenanthridines via Anionic Ring Closure
  作者：Morten Lysén、Jesper L. Kristensen、Per Vedsø、Mikael Begtrup

  DOI：10.1021/ol0170051

  日期：2002.1.1

  [reaction: see text] The addition of organometallic derivatives to the cyano group of 2-(2-fluorophenyl)benzonitrile followed by intramolecular nucleophilic substitution produces 6-substituted phenanthridines. Alkyllithiums, aryllithiums, and sterically nondemanding lithium amides reacted at -78 degrees C to produce the 6-substituted phenanthridines in 82-98% yield upon warming to room temperature

  [反应：见正文]将有机金属衍生物加到2-（2-氟苯基）苄腈的氰基上，然后进行分子内亲核取代，生成6-取代的菲啶。烷基锂，芳基锂和空间上不需要的锂酰胺在-78℃下反应，在升温至室温时以82-98％的产率产生6-取代的菲啶。相应的格氏试剂的添加需要过量的有机金属试剂并在高温下延长反应时间。
• 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.