4-(adamantan-1-yl)-2-quinolinecarbohydrazide | 824935-09-3

• 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: 4-(adamantan-1-yl)-2-quinolinecarbohydrazide
• 英文别名: 4-(1-Adamantyl)quinoline-2-carbohydrazide
• CAS: 824935-09-3
• 化学式: C₂₀H₂₃N₃O
• 分子量: 321.422
• InChiKey: XDAFQKXHTVYZQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(adamantan-1-yl)-2-quinolinecarbohydrazide 、 Boc-O-苄基-L-酪氨酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以68%的产率得到(S)-[2-[N'-(4-adamantan-1-yl-quinoline-2-carbonyl)hydrazino]-1-(4-benzyloxy-benzyl)-2-oxoethyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  含喹啉的4-（金刚烷-1-基）基氨基酸共轭物的合成，抗结核活性和3D-QSAR研究

  摘要：

  描述了两个系列的4-（金刚烷-1-基）基团与氨基酸缀合的喹啉的合成，抗分枝杆菌活性和3D-QSAR研究。最有效的类似物在1.00和3.125μg/ mL之间显示出体外抗分枝杆菌活性。为了了解结构和活性之间的关系，已通过比较分子场分析（CoMFA）进行了3D-QSAR分析。通过场对准生成的CoMFA模型很好地预测了测试集中分子的活性。使用原子拟合比对可获得最佳模型。基于分子领域，结构和活性之间的关系很容易理顺。

  DOI：

  10.1016/j.ejmech.2008.10.004
• 作为产物：
  描述：

  喹哪啶酸 在 盐酸 、 ammonium peroxydisulfate 、 ammonium hydroxide 、 硫酸 、 一水合肼 、 silver nitrate 作用下， 以 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 反应 10.5h， 生成 4-(adamantan-1-yl)-2-quinolinecarbohydrazide
  参考文献：
  名称：

  2,4-二取代喹啉类抗结核药的合成，生物学评价和3D QSAR研究

  摘要：

  报道了三个系列的2，4-二取代喹啉的合成和抗结核活性。评估合成的化合物对结核分枝杆菌H37Rv株的活性。该系列中最有前途的化合物的MIC 99值在3.125至6.25μg/ mL之间。在最高200μg/ mL的最高测试浓度下，没有一种化合物显示出细胞毒性。为了了解结构和活性之间的关系，已通过比较分子场分析（CoMFA）进行了3D-QSAR分析。原子拟合比对提供了最佳模型，并允许预测测试集中分子的活性，从而使结构与活性之间的关系合理化。

  DOI：

  10.1016/j.ejmech.2015.02.034

文献信息

• Synthesis, anti-tuberculosis activity, and 3D-QSAR study of 4-(adamantan-1-yl)-2-substituted quinolines
  作者：Amit Nayyar、Vikramdeep Monga、Alpeshkumar Malde、Evans Coutinho、Rahul Jain

  DOI：10.1016/j.bmc.2006.10.064

  日期：2007.1

  Structural optimization of the previously identified 4-(adamantan-1-yl)-2-quinolinecarbohydrazide (AQCH, MIC=6.25 microg/mL, 99% inhibition, Mycobacterium tuberculosis H37Rv) has led to two series of 4-(adamantan-1-yl)-2-substituted quinolines (Series 1-2). All new derivatives were evaluated in vitro for antimycobacterial activities against drug-sensitive M. tuberculosis H37Rv strain. Several 4-ad

  先前确定的4-（金刚烷-1-基）-2-喹啉碳酰肼（AQCH，MIC = 6.25 microg / mL，99％抑制，结核分枝杆菌H37Rv）的结构优化已导致两个系列的4-（金刚烷-1-烷基）-2-取代的喹啉（1-2系列）。在体外评估了所有新衍生物对药物敏感性结核分枝杆菌H37Rv菌株的抗分枝杆菌活性。本文所述的几种4-金刚烷-1-基-喹啉-2-羧酸N'-烷基酰肼（系列1）显示出有希望的抑制活性。特别是，类似物7、9、20和21的MIC为3.125微克/毫升。通过与各种脂族，芳族和杂芳族醛的反应对AQCH进行进一步研究，导致合成了4-金刚烷-1-基-喹啉-2-羧酸亚烷基酰肼（系列2）。类似物42-44和48在3.125 microg / mL处产生了对药物敏感的结核分枝杆菌H37Rv菌株的有希望的抗分枝杆菌活性（99％抑制）。该系列中最有效的类似物35对1.00克/毫升的药物敏感性菌株产生
• 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, biological evaluation and 3D-QSAR study of hydrazide, semicarbazide and thiosemicarbazide derivatives of 4-(adamantan-1-yl)quinoline as anti-tuberculosis agents
  作者：Sanjay R. Patel、Rahul Gangwal、Abhay T. Sangamwar、Rahul Jain

  DOI：10.1016/j.ejmech.2014.07.100

  日期：2014.10

  We report synthesis, anti-tuberculosis activity and 3D-QSAR study of forty nine hydrazide, semicarbazide and thiosemicarbazide derivatives of 4-(adamantan-1-yl)quinoline. The most potent compounds upon evaluation for anti-tuberculosis activity exhibited MIC99 of 3.125 mu g/mL against Mycobacterium tuberculosis H37Rv strain. We applied the in silica technique of 3D-QSAR to study structure activity relationship of the synthesized compounds. The developed CoMFA model exhibited excellent r(ncv)(2) of 0.971, and r(cv)(2) of 0.543. The predicted r(pred)(2) of 0.883 showed that the predicted values were in good agreement with the experimental values. Further, the contour map analysis, suggested that the sterically bulky and electronegative substitutions at the para position of the phenyl ring are favorable for anti-tuberculosis activity. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis, anti-tuberculosis activity and 3D-QSAR study of amino acid conjugates of 4-(adamantan-1-yl) group containing quinolines
  作者：Amit Nayyar、Sanjay R. Patel、Mushtaque Shaikh、Evans Coutinho、Rahul Jain

  DOI：10.1016/j.ejmech.2008.10.004

  日期：2009.5

  The synthesis, antimycobacterial activity and 3D-QSAR study of two series of 4-(adamantan-1-yl) group containing quinolines conjugated to amino acids are described. The most potent analogs displayed in vitro antimycobacterial activity ranging between 1.00 and 3.125 μg/mL. To understand the relationship between structure and activity, a 3D-QSAR analysis has been carried out by Comparative Molecular

  描述了两个系列的4-（金刚烷-1-基）基团与氨基酸缀合的喹啉的合成，抗分枝杆菌活性和3D-QSAR研究。最有效的类似物在1.00和3.125μg/ mL之间显示出体外抗分枝杆菌活性。为了了解结构和活性之间的关系，已通过比较分子场分析（CoMFA）进行了3D-QSAR分析。通过场对准生成的CoMFA模型很好地预测了测试集中分子的活性。使用原子拟合比对可获得最佳模型。基于分子领域，结构和活性之间的关系很容易理顺。
• Synthesis, biological evaluation and 3D QSAR study of 2,4-disubstituted quinolines as anti-tuberculosis agents
  作者：Sanjay R. Patel、Rahul Gangwal、Abhay T. Sangamwar、Rahul Jain

  DOI：10.1016/j.ejmech.2015.02.034

  日期：2015.3

  The synthesis and anti-tuberculosis activity for three series of 2,4-disubstituted quinolines is reported. The synthesized compounds were evaluated for activity against M. tuberculosis H37Rv strain; most promising compounds from the series exhibited MIC99 values ranged between 3.125 and 6.25 μg/mL. None of the compounds exhibited cytotoxicity up to the highest test concentration of 200 μg/mL. To understand

  报道了三个系列的2，4-二取代喹啉的合成和抗结核活性。评估合成的化合物对结核分枝杆菌H37Rv株的活性。该系列中最有前途的化合物的MIC 99值在3.125至6.25μg/ mL之间。在最高200μg/ mL的最高测试浓度下，没有一种化合物显示出细胞毒性。为了了解结构和活性之间的关系，已通过比较分子场分析（CoMFA）进行了3D-QSAR分析。原子拟合比对提供了最佳模型，并允许预测测试集中分子的活性，从而使结构与活性之间的关系合理化。