7-Methyl-2-(4-(3-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)propanoyl)phenyl)benzo[d]oxazole-5-carbonitrile | 1292821-24-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-Methyl-2-(4-(3-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)propanoyl)phenyl)benzo[d]oxazole-5-carbonitrile
• 英文别名: 7-methyl-2-[4-[3-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]propanoyl]phenyl]-1,3-benzoxazole-5-carbonitrile
• CAS: 1292821-24-9
• 化学式: C₂₉H₂₅F₃N₄O₂
• 分子量: 518.538
• InChiKey: PNKGLAMXBOQUHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  7-Methyl-2-(4-(3-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)propanoyl)phenyl)benzo[d]oxazole-5-carbonitrile 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以45%的产率得到2-(4-(1-Hydroxy-3-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)propyl)phenyl)-7-methylbenzo[d]oxazole-5-carbonitrile
  参考文献：
  名称：

  2-(4-Carbonylphenyl)benzoxazole inhibitors of CETP: Scaffold design and advancement in HDLc-raising efficacy

  摘要：

  The development of 2-phenylbenzoxazoles as inhibitors of cholesteryl ester transfer protein (CETP) is described. Initial efforts aimed at engineering replacements for the aniline substructures in the benchmark molecule. Reversing the connectivity of the central aniline lead to a new class of 2-(4-carbonylphenyl)benzoxazoles. Structure-activity studies at the C-7 and terminal pyridine ring allowed for the optimization of potency and HDLc-raising efficacy in this new class of inhibitors. These efforts lead to the discovery of benzoxazole 11v, which raised HDLc by 24 mg/dl in our transgenic mouse PD model. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.090
• 作为产物：
  描述：

  2-(4-aminophenyl)-7-methyl-1,3-benzoxazole-5-carbonitrile 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 甲酸 、 亚硝酸正戊酯 、 碘 、 mercury(II) sulfate 、 三乙胺 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 生成 7-Methyl-2-(4-(3-(4-(4-(trifluoromethyl)phenyl)piperazin-1-yl)propanoyl)phenyl)benzo[d]oxazole-5-carbonitrile
  参考文献：
  名称：

  2-(4-Carbonylphenyl)benzoxazole inhibitors of CETP: Scaffold design and advancement in HDLc-raising efficacy

  摘要：

  The development of 2-phenylbenzoxazoles as inhibitors of cholesteryl ester transfer protein (CETP) is described. Initial efforts aimed at engineering replacements for the aniline substructures in the benchmark molecule. Reversing the connectivity of the central aniline lead to a new class of 2-(4-carbonylphenyl)benzoxazoles. Structure-activity studies at the C-7 and terminal pyridine ring allowed for the optimization of potency and HDLc-raising efficacy in this new class of inhibitors. These efforts lead to the discovery of benzoxazole 11v, which raised HDLc by 24 mg/dl in our transgenic mouse PD model. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.090

文献信息

• 2-(4-Carbonylphenyl)benzoxazole inhibitors of CETP: Scaffold design and advancement in HDLc-raising efficacy
  作者：Ramzi F. Sweis、Julianne A. Hunt、Florida Kallashi、Milton L. Hammond、Ying Chen、Suzanne S. Eveland、Qiu Guo、Sheryl A. Hyland、Denise P. Milot、Anne-Marie Cumiskey、Melanie Latham、Raymond Rosa、Larry Peterson、Carl P. Sparrow、Samuel D. Wright、Matt S. Anderson、Peter J. Sinclair

  DOI：10.1016/j.bmcl.2010.11.090

  日期：2011.3

  The development of 2-phenylbenzoxazoles as inhibitors of cholesteryl ester transfer protein (CETP) is described. Initial efforts aimed at engineering replacements for the aniline substructures in the benchmark molecule. Reversing the connectivity of the central aniline lead to a new class of 2-(4-carbonylphenyl)benzoxazoles. Structure-activity studies at the C-7 and terminal pyridine ring allowed for the optimization of potency and HDLc-raising efficacy in this new class of inhibitors. These efforts lead to the discovery of benzoxazole 11v, which raised HDLc by 24 mg/dl in our transgenic mouse PD model. (C) 2010 Elsevier Ltd. All rights reserved.