(1R,4R)-1-((S)-1-hydroxy-2-(4-methylpiperazin-1-yl)ethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one | 1615687-93-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,4R)-1-((S)-1-hydroxy-2-(4-methylpiperazin-1-yl)ethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one
• 英文别名: (1R,4R)-1-[(1S)-1-hydroxy-2-(4-methylpiperazin-1-yl)ethyl]-7,7-dimethyl-norbornan-2-one；(1R,4R)-1-[(1S)-1-hydroxy-2-(4-methylpiperazin-1-yl)ethyl]-7,7-dimethylbicyclo[2.2.1]heptan-2-one
• CAS: 1615687-93-8
• 化学式: C₁₆H₂₈N₂O₂
• 分子量: 280.411
• InChiKey: BVYYCUVTCYUKMS-XPKDYRNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (+)-7,7-dimethyl-1-vinyl-2-norbornanone 在 lithium perchlorate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (1R,4R)-1-((S)-1-hydroxy-2-(4-methylpiperazin-1-yl)ethyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  Antimycobacterial activity of chiral aminoalcohols with camphane scaffold

  摘要：

  A series of aminoalcohols were synthesized by reaction of aminolysis of camphor derived oxiranes with chosen amines. The compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv. Ten of the new structures show much higher activity than the classical anti-TB drug ethambutol. Some of the most active compounds were tested against MDR strain 43, and four of them demonstrated excellent activities with MICs 0.27-0.72 mu M. The cytotoxicity of representative exerting antimycobacterial activity compounds was assessed. Quantitative structure activity relationship (QSAR) model is derived to estimate the contribution of each structural fragment to the activity. The camphane-based aminoalcohols are promising lead compounds for further development of novel antimycobacterial agents. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.007

文献信息

• Antimycobacterial activity of chiral aminoalcohols with camphane scaffold
  作者：Zhanina Petkova、Violeta Valcheva、Georgi Momekov、Petar Petrov、Vladimir Dimitrov、Irini Doytchinova、Georgi Stavrakov、Malinka Stoyanova

  DOI：10.1016/j.ejmech.2014.05.007

  日期：2014.6

  A series of aminoalcohols were synthesized by reaction of aminolysis of camphor derived oxiranes with chosen amines. The compounds were evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv. Ten of the new structures show much higher activity than the classical anti-TB drug ethambutol. Some of the most active compounds were tested against MDR strain 43, and four of them demonstrated excellent activities with MICs 0.27-0.72 mu M. The cytotoxicity of representative exerting antimycobacterial activity compounds was assessed. Quantitative structure activity relationship (QSAR) model is derived to estimate the contribution of each structural fragment to the activity. The camphane-based aminoalcohols are promising lead compounds for further development of novel antimycobacterial agents. (C) 2014 Elsevier Masson SAS. All rights reserved.