4-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydrocyclopenta[b]indole | 1388758-36-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydrocyclopenta[b]indole
• CAS: 1388758-36-8
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: VLUHZYSHKWAPKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  17.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydrocyclopenta[b]indole 、 2-巯基甲苯 在 水 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 1-(2,3-dihydrocyclopenta[b]indol-4(1H)-yl)-3-(o-tolylthio)propan-2-ol
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies of 1,3-disubstituted 2-propanols as BACE-1 inhibitors

  摘要：

  A library of 1,3-disubstituted 2-propanols was synthesized and evaluated as low molecular weight probes for beta-secretase inhibition. By screening a library of 121 1,3-disubstituted 2-propanol derivatives, we identified few compounds inhibiting the enzyme at low micromolar concentrations. The initial hits were optimized to yield a potent BACE-1 inhibitor exhibiting an IC50 constant in the nanomolar range. Exploration of the pharmacological properties revealed that these small molecular inhibitors possessed a high selectivity over cathepsin D and desirable physicochemical properties beneficial to cross the blood-brain barrier. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.072
• 作为产物：
  描述：

  1,2,3,4-四氢环戊[b]吲哚 、 环氧氯丙烷 在 tetrapropylammonium iodide 、 potassium hydroxide 作用下， 以92.2%的产率得到4-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydrocyclopenta[b]indole
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies of 1,3-disubstituted 2-propanols as BACE-1 inhibitors

  摘要：

  A library of 1,3-disubstituted 2-propanols was synthesized and evaluated as low molecular weight probes for beta-secretase inhibition. By screening a library of 121 1,3-disubstituted 2-propanol derivatives, we identified few compounds inhibiting the enzyme at low micromolar concentrations. The initial hits were optimized to yield a potent BACE-1 inhibitor exhibiting an IC50 constant in the nanomolar range. Exploration of the pharmacological properties revealed that these small molecular inhibitors possessed a high selectivity over cathepsin D and desirable physicochemical properties beneficial to cross the blood-brain barrier. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.072