1-(5-methoxy-2-pyridinyl)cyclohexanecarbonitrile | 204067-35-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-methoxy-2-pyridinyl)cyclohexanecarbonitrile
• 英文别名: 1-(5-methoxypyridin-2-yl)cyclohexane-1-carbonitrile
• CAS: 204067-35-6
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: UUIUFBITJNNTSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  45.91
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(5-methoxy-2-pyridinyl)cyclohexanecarbonitrile 在 氨 、 氢气 、 N,N'-羰基二咪唑 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 21.0h， 生成 (R)-[1-(1H-indol-3-ylmethyl)-2-[[[1-(5-methoxy-2-pyridinyl)cyclohexyl]methyl]amino]-2-oxoethyl]carbamic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  Novel 3-(1H-indol-3-yl)-2-[3-(4-methoxyphenyl)ureido]propanamides as selective agonists of human formyl-peptide receptor 2

  摘要：

  N-Formyl peptide receptors (FPRs) are G protein-coupled receptors (GPCRs) that play critical roles in inflammatory reactions, and FPR-specific interactions can possibly be used to facilitate the resolution of pathological inflammatory reactions. We here report the synthesis and biological evaluation of six pairs of chiral ureidopropanamido derivatives as potent and selective formyl peptide receptor-2 (FPR2) agonists that were designed starting from our lead agonist (S)-3-(1H-indol-3-yl)-2-[3-(4-methoxyphenyl)ureido]-N-[[1-(5-methoxy-2-pyridinyl)cyclohexyl]methyl]propanamide ((S)-9a). The new compounds were obtained in overall yields considerably higher than (S)-9a. Several of the new compounds showed agonist properties comparable to that of (S)-9a along with higher selectivity over FPR1. Molecular modeling was used to define chiral recognition by FPR2. In vitro metabolic stability of selected compounds was also assessed to obtain preliminary insight on drug-like properties of this class of compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.007
• 作为产物：
  描述：

  2-甲基-5-甲氧基吡啶氮氧化物 在 氯化亚砜 、 水 、 sodium hydride 、 potassium hydroxide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 29.17h， 生成 1-(5-methoxy-2-pyridinyl)cyclohexanecarbonitrile
  参考文献：
  名称：

  Novel 3-(1H-indol-3-yl)-2-[3-(4-methoxyphenyl)ureido]propanamides as selective agonists of human formyl-peptide receptor 2

  摘要：

  N-Formyl peptide receptors (FPRs) are G protein-coupled receptors (GPCRs) that play critical roles in inflammatory reactions, and FPR-specific interactions can possibly be used to facilitate the resolution of pathological inflammatory reactions. We here report the synthesis and biological evaluation of six pairs of chiral ureidopropanamido derivatives as potent and selective formyl peptide receptor-2 (FPR2) agonists that were designed starting from our lead agonist (S)-3-(1H-indol-3-yl)-2-[3-(4-methoxyphenyl)ureido]-N-[[1-(5-methoxy-2-pyridinyl)cyclohexyl]methyl]propanamide ((S)-9a). The new compounds were obtained in overall yields considerably higher than (S)-9a. Several of the new compounds showed agonist properties comparable to that of (S)-9a along with higher selectivity over FPR1. Molecular modeling was used to define chiral recognition by FPR2. In vitro metabolic stability of selected compounds was also assessed to obtain preliminary insight on drug-like properties of this class of compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.007