3,3,5-trimethyl-1-(5-methyl-4H-1,2,4-triazol-3-yl)cyclohexanol | 1373018-72-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3,5-trimethyl-1-(5-methyl-4H-1,2,4-triazol-3-yl)cyclohexanol
• 英文别名: 3,3,5-trimethyl-1-(5-methyl-1H-1,2,4-triazol-3-yl)cyclohexan-1-ol
• CAS: 1373018-72-4
• 化学式: C₁₂H₂₁N₃O
• 分子量: 223.318
• InChiKey: BDWMGBLEVUMDJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,3,5-三甲基环己酮 在 potassium carbonate 、 sodium hydrogensulfite 作用下， 以 水 、 正丁醇 为溶剂， 反应 1.75h， 生成 3,3,5-trimethyl-1-(5-methyl-4H-1,2,4-triazol-3-yl)cyclohexanol
  参考文献：
  名称：

  Novel 4H-1,2,4-triazol-3-yl cycloalkanols as potent antitubercular agents

  摘要：

  Enzymes of shikimate pathway, dehydroquinase and shikimate kinase represent comparatively newer targets for antitubercular research. Molecular hybridization approach was implemented by integrating the essential features of inhibitors acting on these enzymes of shikimate pathway. Considering the flexibility of alicyclic ring of reported dehydroquinase (DHQ) inhibitors and triazole ring, key feature of the virtual hits of Mtb shikimate kinase, a series of structurally novel, substituted 4H-1,2,4-triazol-3-yl cycloalkanols were designed as antimycobacterial agents. Docking studies of the molecules was carried out on the enzyme DHQ. All the synthesized compounds exhibited promising activity (MIC 0.59-15.5 mu g/ml) against H(37)Rv strains of Mycobacterium tuberculosis using resazurin microtiter assay. Five of the evaluated compounds exhibit MIC < 1 mu g/ml. CC50 values indicate compounds are non-toxic, with selectivity indices >28. These compounds could serve as leads for further optimization to obtain novel antimycobacterial agents.

  DOI：

  10.1007/s00044-012-0043-9

文献信息

• Novel 4H-1,2,4-triazol-3-yl cycloalkanols as potent antitubercular agents
  作者：Nutan H. Palsule Desai、Ranjeet Bairwa、Manoj Kakwani、Nilesh Tawari、M. K. Ray、M. G. Rajan、Mariam Degani

  DOI：10.1007/s00044-012-0043-9

  日期：2013.1

  Enzymes of shikimate pathway, dehydroquinase and shikimate kinase represent comparatively newer targets for antitubercular research. Molecular hybridization approach was implemented by integrating the essential features of inhibitors acting on these enzymes of shikimate pathway. Considering the flexibility of alicyclic ring of reported dehydroquinase (DHQ) inhibitors and triazole ring, key feature of the virtual hits of Mtb shikimate kinase, a series of structurally novel, substituted 4H-1,2,4-triazol-3-yl cycloalkanols were designed as antimycobacterial agents. Docking studies of the molecules was carried out on the enzyme DHQ. All the synthesized compounds exhibited promising activity (MIC 0.59-15.5 mu g/ml) against H(37)Rv strains of Mycobacterium tuberculosis using resazurin microtiter assay. Five of the evaluated compounds exhibit MIC < 1 mu g/ml. CC50 values indicate compounds are non-toxic, with selectivity indices >28. These compounds could serve as leads for further optimization to obtain novel antimycobacterial agents.