1-ethyl-3-((1S,2R,3S,4R)-3-hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)urea

• 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: 1-ethyl-3-((1S,2R,3S,4R)-3-hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)urea
• 英文别名: 1-ethyl-3-[(1S,2R,3S,4R)-3-hydroxy-4,7,7-trimethyl-norbornan-2-yl]urea；1-ethyl-3-[(1S,2R,3S,4R)-3-hydroxy-4,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl]urea
• 化学式: C₁₃H₂₄N₂O₂
• 分子量: 240.346
• InChiKey: VZHWVPKANHHFMN-PRFIWBCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-氨基-1,7,7-三甲基-双环[2,2,1]庚-2-醇 、 异氰酸乙酯 以 二氯甲烷 为溶剂， 反应 2.5h， 以76%的产率得到1-ethyl-3-((1S,2R,3S,4R)-3-hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-yl)urea
  参考文献：
  名称：

  Novel camphane-based anti-tuberculosis agents with nanomolar activity

  摘要：

  A series of new amidoalcohols and amidodiols were designed on the base of the camphor scaffold and evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv and MDR strain 43. Some of the new compounds show 25 times higher activity than the classical anti-TB drug ethambutol. Small structural changes in the side chain shift the activity from micromolar to nanomolar inhibitory concentrations. Quantitative structure activity relationship (QSAR) model is derived to guide the further lead optimization. Two hydrogen bond donors and up to three rings in the molecules are optimal for nanomolar activity. The camphane-based amides present novel promising scaffolds for antimycobacterial agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.015

文献信息

• Novel camphane-based anti-tuberculosis agents with nanomolar activity
  作者：Georgi Stavrakov、Violeta Valcheva、Irena Philipova、Irini Doytchinova

  DOI：10.1016/j.ejmech.2013.10.015

  日期：2013.12

  A series of new amidoalcohols and amidodiols were designed on the base of the camphor scaffold and evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv and MDR strain 43. Some of the new compounds show 25 times higher activity than the classical anti-TB drug ethambutol. Small structural changes in the side chain shift the activity from micromolar to nanomolar inhibitory concentrations. Quantitative structure activity relationship (QSAR) model is derived to guide the further lead optimization. Two hydrogen bond donors and up to three rings in the molecules are optimal for nanomolar activity. The camphane-based amides present novel promising scaffolds for antimycobacterial agents. (C) 2013 Elsevier Masson SAS. All rights reserved.