1-(5-(5-(chloromethyl)pyridin-2-yl))-7-phenylheptan-1-one | 1542234-92-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-(5-(chloromethyl)pyridin-2-yl))-7-phenylheptan-1-one
• 英文别名: 1-[5-[5-(Chloromethyl)pyridin-2-yl]-1,3-oxazol-2-yl]-7-phenylheptan-1-one；1-[5-[5-(chloromethyl)pyridin-2-yl]-1,3-oxazol-2-yl]-7-phenylheptan-1-one
• CAS: 1542234-92-3
• 化学式: C₂₂H₂₃ClN₂O₂
• 分子量: 382.89
• InChiKey: ATPMWXKNVYBCEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  56
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5-(5-(chloromethyl)pyridin-2-yl))-7-phenylheptan-1-one 、 sodium thiomethoxide 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以42%的产率得到1-(5-(5-((methylthio)methyl)pyridin-2-yl))-7-phenylheptan-1-one
  参考文献：
  名称：

  Design, Synthesis, and Characterization of α-Ketoheterocycles That Additionally Target the Cytosolic Port Cys269 of Fatty Acid Amide Hydrolase

  摘要：

  A series of alpha-ketooxazoles incorporating electrophiles at the C5 position of the pyridyl ring of 2 (OL-135) and related compounds were prepared and examined as inhibitors of fatty acid amide hydrolase (FAAH) that additionally target the cytosolic port Cys269. From this series, a subset of the candidate inhibitors exhibited time-dependent FAAH inhibition and noncompetitive irreversible inactivation of the enzyme, consistent with the targeted Cys269 covalent alkylation or addition, and maintained or enhanced the intrinsic selectivity for FAAH versus other serine hydrolases. A preliminary in vivo assessment demonstrates that these inhibitors raise endogenous brain levels of anandamide and other FAAH substrates upon intraperitoneal (i.p.) administration to mice, with peak levels achieved within 1.5-3 h, and that the elevations of the signaling lipids were maintained >6 h, indicating that the inhibitors effectively reach and remain active in the brain, inhibiting FAAH for a sustained period.

  DOI：

  10.1021/jm401820q
• 作为产物：
  描述：

  6-氯烟酸甲酯 在 盐酸 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 氯化亚砜 、 四丁基氟化铵 、 戴斯-马丁氧化剂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 1-(5-(5-(chloromethyl)pyridin-2-yl))-7-phenylheptan-1-one
  参考文献：
  名称：

  Design, Synthesis, and Characterization of α-Ketoheterocycles That Additionally Target the Cytosolic Port Cys269 of Fatty Acid Amide Hydrolase

  摘要：

  A series of alpha-ketooxazoles incorporating electrophiles at the C5 position of the pyridyl ring of 2 (OL-135) and related compounds were prepared and examined as inhibitors of fatty acid amide hydrolase (FAAH) that additionally target the cytosolic port Cys269. From this series, a subset of the candidate inhibitors exhibited time-dependent FAAH inhibition and noncompetitive irreversible inactivation of the enzyme, consistent with the targeted Cys269 covalent alkylation or addition, and maintained or enhanced the intrinsic selectivity for FAAH versus other serine hydrolases. A preliminary in vivo assessment demonstrates that these inhibitors raise endogenous brain levels of anandamide and other FAAH substrates upon intraperitoneal (i.p.) administration to mice, with peak levels achieved within 1.5-3 h, and that the elevations of the signaling lipids were maintained >6 h, indicating that the inhibitors effectively reach and remain active in the brain, inhibiting FAAH for a sustained period.

  DOI：

  10.1021/jm401820q