(7-(benzyloxy)chroman-3-yl)(5-(pyridin-2-yl)oxazol-2-yl)methanone | 1607825-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (7-(benzyloxy)chroman-3-yl)(5-(pyridin-2-yl)oxazol-2-yl)methanone
• 英文别名: [(3R)-7-phenylmethoxy-3,4-dihydro-2H-chromen-3-yl]-(5-pyridin-2-yl-1,3-oxazol-2-yl)methanone
• CAS: 1607825-99-9
• 化学式: C₂₅H₂₀N₂O₄
• 分子量: 412.445
• InChiKey: LKKWQRMAYIEENV-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7-(benzyloxy)chroman-3-carboxaldehyde 在 咪唑 、 四(三苯基膦)钯 、 正丁基锂 、 硼烷四氢呋喃络合物 、 四丁基氟化铵 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 (7-(benzyloxy)chroman-3-yl)(5-(pyridin-2-yl)oxazol-2-yl)methanone 、 (7-(benzyloxy)chroman-3-yl)(5-(pyridin-2-yl)oxazol-2-yl)methanone
  参考文献：
  名称：

  α-Ketoheterocycle inhibitors of fatty acid amide hydrolase: Exploration of conformational constraints in the acyl side chain

  摘要：

  A series of alpha-ketooxazoles containing heteroatoms embedded within conformational constraints in the C2 acyl side chain of 2 (OL-135) were synthesized and evaluated as inhibitors of fatty acid amide hydrolase (FAAH). The studies reveal that the installation of a heteroatom (O) in the conformational constraint is achievable, although the potency of these novel derivatives is reduced slightly relative to 2 and the analogous 1,2,3,4-tetrahydronaphthalene series. Interestingly, both enantiomers (R and S) of the candidate inhibitors bearing a chiral center adjacent to the electrophilic carbonyl were found to effectively inhibit FAAH. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.013

文献信息

• α-Ketoheterocycle inhibitors of fatty acid amide hydrolase: Exploration of conformational constraints in the acyl side chain
  作者：Katharine K. Duncan、Katerina Otrubova、Dale L. Boger

  DOI：10.1016/j.bmc.2014.03.013

  日期：2014.5

  A series of alpha-ketooxazoles containing heteroatoms embedded within conformational constraints in the C2 acyl side chain of 2 (OL-135) were synthesized and evaluated as inhibitors of fatty acid amide hydrolase (FAAH). The studies reveal that the installation of a heteroatom (O) in the conformational constraint is achievable, although the potency of these novel derivatives is reduced slightly relative to 2 and the analogous 1,2,3,4-tetrahydronaphthalene series. Interestingly, both enantiomers (R and S) of the candidate inhibitors bearing a chiral center adjacent to the electrophilic carbonyl were found to effectively inhibit FAAH. (C) 2014 Elsevier Ltd. All rights reserved.