1-[(2R)-oxiran-2-ylmethyl]-3a,7a-dihydro-1H-indole-3-carboxaldehyde

• 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: 1-[(2R)-oxiran-2-ylmethyl]-3a,7a-dihydro-1H-indole-3-carboxaldehyde
• 英文别名: 1-[[(2R)-oxiran-2-yl]methyl]indole-3-carbaldehyde
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: CWPXSZCBFXTZHJ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(2R)-oxiran-2-ylmethyl]-3a,7a-dihydro-1H-indole-3-carboxaldehyde 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-{1-[(2R)-2-hydroxy-3-(5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yloxy)propyl]-1H-indol-3-ylmethylene}pyrimidine-2,4,6-trione
  参考文献：
  名称：

  Triblock Conjugates: Identification of a Highly Potent Antiinflammatory Agent

  摘要：

  Rationally designed conjugates of chrysin, indole, and barbituric acid were synthesized and screened for their antiinflammatory activities through in vitro and in vivo experiments. Improved over the previously reported chrysin indole pyrazole conjugates and also in comparison to the chrysin, indole, and barbituric acid based COX-2 inhibitors, the new compounds have displayed significantly better IC50 for COX-2 and some of them also exhibited inhibition of 5-LOX enzyme. For one of the test compounds, IC50 for COX-2 and 5-LOX was 1 and 1.5 nM, respectively. Investigations of Swiss Albino mice through capsaicin induced paw lickings and dextran induced inflammation showed that these compounds possess appreciable analgesic and antiinflammatory activities. K-i, K-a, and Delta G for the enzyme compound interaction were calculated and found to be in agreement with The experimental results were supported by the molecular docking studies of the compounds in the active site of COX-2 and 5-LOX. Overall, a highly promising antiinflammatory agent was identified. the biological data.

  DOI：

  10.1021/acs.jmedchem.5b00952
• 作为产物：
  描述：

  3-吲哚甲醛 、 左旋环氧氯丙烷 在 sodium hydride 作用下， 以 乙腈 为溶剂， 生成 1-[(2R)-oxiran-2-ylmethyl]-3a,7a-dihydro-1H-indole-3-carboxaldehyde
  参考文献：
  名称：

  Triblock Conjugates: Identification of a Highly Potent Antiinflammatory Agent

  摘要：

  Rationally designed conjugates of chrysin, indole, and barbituric acid were synthesized and screened for their antiinflammatory activities through in vitro and in vivo experiments. Improved over the previously reported chrysin indole pyrazole conjugates and also in comparison to the chrysin, indole, and barbituric acid based COX-2 inhibitors, the new compounds have displayed significantly better IC50 for COX-2 and some of them also exhibited inhibition of 5-LOX enzyme. For one of the test compounds, IC50 for COX-2 and 5-LOX was 1 and 1.5 nM, respectively. Investigations of Swiss Albino mice through capsaicin induced paw lickings and dextran induced inflammation showed that these compounds possess appreciable analgesic and antiinflammatory activities. K-i, K-a, and Delta G for the enzyme compound interaction were calculated and found to be in agreement with The experimental results were supported by the molecular docking studies of the compounds in the active site of COX-2 and 5-LOX. Overall, a highly promising antiinflammatory agent was identified. the biological data.

  DOI：

  10.1021/acs.jmedchem.5b00952

文献信息

• Triblock Conjugates: Identification of a Highly Potent Antiinflammatory Agent
  作者：Palwinder Singh、Jagroop Kaur、Gurjit Singh、Rajbir Bhatti

  DOI：10.1021/acs.jmedchem.5b00952

  日期：2015.8.13

  Rationally designed conjugates of chrysin, indole, and barbituric acid were synthesized and screened for their antiinflammatory activities through in vitro and in vivo experiments. Improved over the previously reported chrysin indole pyrazole conjugates and also in comparison to the chrysin, indole, and barbituric acid based COX-2 inhibitors, the new compounds have displayed significantly better IC50 for COX-2 and some of them also exhibited inhibition of 5-LOX enzyme. For one of the test compounds, IC50 for COX-2 and 5-LOX was 1 and 1.5 nM, respectively. Investigations of Swiss Albino mice through capsaicin induced paw lickings and dextran induced inflammation showed that these compounds possess appreciable analgesic and antiinflammatory activities. K-i, K-a, and Delta G for the enzyme compound interaction were calculated and found to be in agreement with The experimental results were supported by the molecular docking studies of the compounds in the active site of COX-2 and 5-LOX. Overall, a highly promising antiinflammatory agent was identified. the biological data.