4-环戊基喹啉-2-羧酸甲酯 | 753487-54-6

• 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: 4-环戊基喹啉-2-羧酸甲酯
• 英文名称: methyl 4-cyclopentyl-2-quinolinecarboxylate
• 英文别名: Methyl 4-cyclopentylquinoline-2-carboxylate
• CAS: 753487-54-6
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: CEWONNKTYJXHMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-环戊基喹啉-2-羧酸甲酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以98%的产率得到4-Cyclopentyl-quinoline-2-carboxylic acid hydrazide
  参考文献：
  名称：

  Ring-substituted quinolines. Part 2: Synthesis and antimycobacterial activities of ring-substituted quinolinecarbohydrazide and ring-substituted quinolinecarboxamide analogues

  摘要：

  Additional structural modifications of the new chemical entity, 2,8-dicyclopentyl-4-methylquinoline (DCMQ; MIC = 6.25mug/mL, M. tuberculosis H37Rv) resulted in the synthesis of four new series of the ring-substituted quinolinecarbohydrazides (series 1-4) constituting 22 analogues. All new derivatives were evaluated for in vitro antimycobacterial activities against drug-sensitive M. tuberculosis H37Rv strain. Certain ring-substituted-2-quinolinecarbohydrazide analogues described herein showed good inhibitory activity. In particular, analogues 4-(1-adamantyl)-2-quinolinecarbohydrazide (2d), 4,5-dicyclopentyl-2-quinolinecarbohydrazide (2e), 4,8-dicyclopentyl-2-quinolinecarbohydrazide (2f), and 4,5-dicyclohexyl-2-quinolinecarbohydrazide (2g) have exhibited the MIC value of 6.25ltg/mL. Further investigation of the most suitable lead prototype, 4-(1-adamantyl)-2-quinolinecarbohydrazide (2d, series 1) led to the synthesis of N2-alkyl/N2,N2-dialkyl/N2-aryl-4-(1-adamantyl)-2-quinolinecarboxamides (series 5) consisting of 13 analogues. Some of the synthesized carboxamides 7a, 7h, and 7m reported herein have exhibited excellent antimycobacterial activities in the range of 6.25-3.1251mug/mL against drug-sensitive and drug-resistant M. tuberculosis H37 Rv strains.

  DOI：

  10.1016/j.bmc.2004.09.017
• 作为产物：
  描述：

  喹哪啶酸 在 盐酸 、 ammonium persulfate 、 硫酸 、 silver nitrate 作用下， 以 水 为溶剂， 反应 0.5h， 生成 4-环戊基喹啉-2-羧酸甲酯
  参考文献：
  名称：

  环取代的喹啉羧酸/酯类似物的合成和抗分枝杆菌活性。第1部分。

  摘要：

  最近发现的新化学实体2,8-二环戊基-4-甲基喹啉（DCMQ; MIC = 6.25 microg / mL，结核分枝杆菌H37Rv）的结构优化导致合成了四个新系列的环取代喹啉羧酸/酯45个类似物。评估了所有新的衍生物对结核分枝杆菌H37Rv的体外抗分枝杆菌活性。本文所述的某些环取代的2-喹啉羧酸酯和环取代的-2-喹啉乙酸酯类似物显示出中等至良好的抑制活性。特别是三种类似物4,5,5-二环戊基-2-喹啉羧酸甲酯（3b），4,8-二环戊基-2-喹啉羧酸甲酯（3c）和2-（2,8-二环戊基-4-喹啉基）乙酸乙酯（14g ）分别具有1.00、2.00和4.00microg / mL的极佳MIC值。

  DOI：

  10.1016/j.bmc.2004.05.018

文献信息

• Ring-substituted quinolines. Part 2: Synthesis and antimycobacterial activities of ring-substituted quinolinecarbohydrazide and ring-substituted quinolinecarboxamide analogues
  作者：Vikramdeep Monga、Amit Nayyar、Balasubramanian Vaitilingam、Prakash B. Palde、Sarbjit Singh Jhamb、Sukhraj Kaur、Prati Pal Singh、Rahul Jain

  DOI：10.1016/j.bmc.2004.09.017

  日期：2004.12

  Additional structural modifications of the new chemical entity, 2,8-dicyclopentyl-4-methylquinoline (DCMQ; MIC = 6.25mug/mL, M. tuberculosis H37Rv) resulted in the synthesis of four new series of the ring-substituted quinolinecarbohydrazides (series 1-4) constituting 22 analogues. All new derivatives were evaluated for in vitro antimycobacterial activities against drug-sensitive M. tuberculosis H37Rv strain. Certain ring-substituted-2-quinolinecarbohydrazide analogues described herein showed good inhibitory activity. In particular, analogues 4-(1-adamantyl)-2-quinolinecarbohydrazide (2d), 4,5-dicyclopentyl-2-quinolinecarbohydrazide (2e), 4,8-dicyclopentyl-2-quinolinecarbohydrazide (2f), and 4,5-dicyclohexyl-2-quinolinecarbohydrazide (2g) have exhibited the MIC value of 6.25ltg/mL. Further investigation of the most suitable lead prototype, 4-(1-adamantyl)-2-quinolinecarbohydrazide (2d, series 1) led to the synthesis of N2-alkyl/N2,N2-dialkyl/N2-aryl-4-(1-adamantyl)-2-quinolinecarboxamides (series 5) consisting of 13 analogues. Some of the synthesized carboxamides 7a, 7h, and 7m reported herein have exhibited excellent antimycobacterial activities in the range of 6.25-3.1251mug/mL against drug-sensitive and drug-resistant M. tuberculosis H37 Rv strains.
• Synthesis and antimycobacterial activities of ring-substituted quinolinecarboxylic acid/ester analogues. Part 1
  作者：Balasubramanian Vaitilingam、Amit Nayyar、Prakash B Palde、Vikramdeep Monga、Rahul Jain、Sukhraj Kaur、Prati Pal Singh

  DOI：10.1016/j.bmc.2004.05.018

  日期：2004.8.1

  discovered new chemical entity, 2,8-dicyclopentyl-4-methylquinoline (DCMQ; MIC= 6.25 microg/mL, M. tuberculosis H37Rv) resulted in the synthesis of four new series of ring-substituted quinolinecarboxylic acids/esters constituting 45 analogues. All new derivatives were evaluated for in vitro antimycobacterial activities against M. tuberculosis H37Rv. Certain ring-substituted-2-quinolinecarboxylic acid ester

  最近发现的新化学实体2,8-二环戊基-4-甲基喹啉（DCMQ; MIC = 6.25 microg / mL，结核分枝杆菌H37Rv）的结构优化导致合成了四个新系列的环取代喹啉羧酸/酯45个类似物。评估了所有新的衍生物对结核分枝杆菌H37Rv的体外抗分枝杆菌活性。本文所述的某些环取代的2-喹啉羧酸酯和环取代的-2-喹啉乙酸酯类似物显示出中等至良好的抑制活性。特别是三种类似物4,5,5-二环戊基-2-喹啉羧酸甲酯（3b），4,8-二环戊基-2-喹啉羧酸甲酯（3c）和2-（2,8-二环戊基-4-喹啉基）乙酸乙酯（14g ）分别具有1.00、2.00和4.00microg / mL的极佳MIC值。