rac-4-(5-cyano-7-isopropylbenzo[d]oxazol-2-yl)-N-((3-(5-(5-methylthiophen-2-yl)pyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)benzamide | 1093752-45-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: rac-4-(5-cyano-7-isopropylbenzo[d]oxazol-2-yl)-N-((3-(5-(5-methylthiophen-2-yl)pyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)benzamide
• 英文别名: 4-(5-cyano-7-propan-2-yl-1,3-benzoxazol-2-yl)-N-[[3-[5-(5-methylthiophen-2-yl)pyridin-2-yl]-2-oxo-1,3-oxazolidin-5-yl]methyl]benzamide
• CAS: 1093752-45-4
• 化学式: C₃₂H₂₇N₅O₄S
• 分子量: 577.663
• InChiKey: IZBGYRCJSTWJCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 rac-4-(5-cyano-7-isopropylbenzo[d]oxazol-2-yl)-N-((3-(5-(5-methylthiophen-2-yl)pyridin-2-yl)-2-oxooxazolidin-5-yl)methyl)benzamide
  参考文献：
  名称：

  2-(4-Carbonylphenyl)benzoxazole inhibitors of CETP: Attenuation of hERG binding and improved HDLc-raising efficacy

  摘要：

  The development of 2-phenylbenzoxazoles as inhibitors of cholesteryl ester transfer protein (CETP) is described. Efforts focused on finding suitable replacements for the central piperidine with the aim of reducing hERG binding: a main liability of our benchmark benzoxazole (1a). Replacement of the piperidine with a cyclohexyl group successfully attenuated hERG binding, but was accompanied by reduced in vivo efficacy. The approach of substituting a piperidine moiety with an oxazolidinone also attenuated hERG binding. Further refinement of this latter scaffold via SAR at the pyridine terminus and methyl branching on the oxazolidinone led to compounds 7e and 7f, which raised HDLc by 33 and 27 mg/dl, respectively, in our transgenic mouse PD model and without the hERG liability of previous series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.049