16-phenyl-6,7,8,9,10,11,12,13,14,15-decahydro-5-azacyclododeca[b]naphthalene | 1160271-67-9

• 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: 16-phenyl-6,7,8,9,10,11,12,13,14,15-decahydro-5-azacyclododeca[b]naphthalene
• 英文别名: 2-chloro-11-phenyl-6H-indeno[2,1-b]quinoline
• CAS: 1160271-67-9
• 化学式: C₂₂H₁₄ClN
• 分子量: 327.813
• InChiKey: DBYUGKLYZNVOAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氨基-5-氯二苯甲酮 、 2-茚酮 在 三氟乙酸 作用下， 以 neat (no solvent) 为溶剂， 反应 0.1h， 以81%的产率得到16-phenyl-6,7,8,9,10,11,12,13,14,15-decahydro-5-azacyclododeca[b]naphthalene
  参考文献：
  名称：

  Design, synthesis and evaluation of acridine and fused-quinoline derivatives as potential anti-tuberculosis agents

  摘要：

  The synthesis of twelve acridine and polycyclic acridine derivatives prepared via the Friedlander reaction is described. The one-pot reactions of 2-amino-5-chloro or 5-nitro-benzophenones and a variety of cydanones and indanones were carried out in a MW oven under TFA catalysis in good yields. The products were designed according natural antituberculosis products and were evaluated for growth inhibitory activity towards Mycobacterium tuberculosis H(37)Rv (Mtb) through the National Institute of Allergy and Infectious Diseases (NIAID, USA). Three of them underwent additional testings. The cyclopenta[b]quinoline derivative 9 and the acridine derivative 13 showed remarkable MIC values against the rifampin resistant strain. The former exhibited bactericidal activity at 50 mu g/mL, its intracellular activity is similar to rifampin and it was not cytotoxic at low concentrations so it can be considered a new lead compound. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.013

文献信息

• (Bromodimethyl)sulfonium Bromide Catalyzed Solvent-Free Friedlander Synthesis of Substituted Quinolines
  作者：R. Venkatesham、A. Manjula、B. Vittal Rao

  DOI：10.1002/jhet.873

  日期：2012.7

  A simple and efficient (bromodimethyl)sulfonium bromide catalyzed synthesis of quinolines, by condensation of α‐amino carbonyl, that is, 2‐aminobenzophenone and 2‐aminoacetophenone with α‐methylene containing carbonyl like 1,3‐dicarbonyls has been developed. The reaction is versatile, solvent‐free protocol for generation of structurally diverse quinolines.

  通过α-氨基羰基（即2-氨基二苯甲酮和2-氨基苯乙酮）与含α-亚甲基的羰基（如1,3-二羰基）的缩合反应，开发了一种简单有效的溴化（溴二甲基）ulf喹啉催化合成方法。该反应是通用的，无溶剂的方案，可生成结构多样的喹啉。
• Design, synthesis and evaluation of acridine and fused-quinoline derivatives as potential anti-tuberculosis agents
  作者：Gisela C. Muscia、Graciela Y. Buldain、Silvia E. Asís

  DOI：10.1016/j.ejmech.2013.12.013

  日期：2014.2

  The synthesis of twelve acridine and polycyclic acridine derivatives prepared via the Friedlander reaction is described. The one-pot reactions of 2-amino-5-chloro or 5-nitro-benzophenones and a variety of cydanones and indanones were carried out in a MW oven under TFA catalysis in good yields. The products were designed according natural antituberculosis products and were evaluated for growth inhibitory activity towards Mycobacterium tuberculosis H(37)Rv (Mtb) through the National Institute of Allergy and Infectious Diseases (NIAID, USA). Three of them underwent additional testings. The cyclopenta[b]quinoline derivative 9 and the acridine derivative 13 showed remarkable MIC values against the rifampin resistant strain. The former exhibited bactericidal activity at 50 mu g/mL, its intracellular activity is similar to rifampin and it was not cytotoxic at low concentrations so it can be considered a new lead compound. (C) 2013 Elsevier Masson SAS. All rights reserved.