2-(1-Adamantyl)-4-hydrazidoquinoline | 119778-67-5

• 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: 2-(1-Adamantyl)-4-hydrazidoquinoline
• 英文别名: 2-(1-Adamantyl)-4-quinolinecarbohydrazide；2-(1-adamantyl)quinoline-4-carbohydrazide
• CAS: 119778-67-5
• 化学式: C₂₀H₂₃N₃O
• 分子量: 321.422
• InChiKey: SHBVMORRRJEXOD-UHFFFAOYSA-N

物化性质

• 熔点：
  108 °C
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：

  2-(1-Adamantyl)-4-hydrazidoquinoline 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 5.0h， 生成 2-(1-Adamantyl)-4-ethoxycarbonylaminoquinoline
  参考文献：
  名称：

  Synthesis and antimicrobial activity of 4-substituted 2-cycloalkylquinolines

  摘要：

  DOI：

  10.1007/bf00771640
• 作为产物：
  描述：

  1-金刚烷甲酮 在 ammonium hydroxide 、 硫酸 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 23.0h， 生成 2-(1-Adamantyl)-4-hydrazidoquinoline
  参考文献：
  名称：

  Synthesis and antimicrobial activity of 4-substituted 2-cycloalkylquinolines

  摘要：

  DOI：

  10.1007/bf00771640

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 antimicrobial activity of 4-substituted 2-cycloalkylquinolines
  作者：I. K. Moiseev、M. N. Zemtsova、P. L. Trakhtenberg、D. A. Kulikova、I. P. Skobkina、G. N. Neshchadim、N. V. Ostapchuk

  DOI：10.1007/bf00771640

  日期：1988.12