5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-1,3-oxazolidin-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-1,3-oxazolidin-2-one
• 英文别名: (5S)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[[2-(2-methoxy-5-propan-2-ylphenyl)-5-(trifluoromethyl)phenyl]methyl]-1,3-oxazolidin-2-one
• 化学式: C₂₉H₂₄F₉NO₃
• 分子量: 605.5
• InChiKey: BZUZYNFRONCFPJ-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  4-氨基-3-碘三氟甲苯 在 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 亚硝酸特丁酯 、 二碘甲烷 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 2-甲基-1,2-丙二醇 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 23.59h， 生成 5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-1,3-oxazolidin-2-one 、 5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Discovery of Substituted Biphenyl Oxazolidinone Inhibitors of Cholesteryl Ester Transfer Protein

  摘要：

  Recently, there has been a strong interest in the ability to increase levels of high density lipoprotein-cholesterol (HDL-C). This interest stems from the hypothesis that such an elevation in HDL-C will decrease the likelihood of cardiovascular disease. Inhibition of cholesteryl ester transfer protein (CETP) has been shown to elevate HDL-C levels in human subjects. This letter describes the discovery of a novel and potent (<100 nM IC(50) for the inhibition of CE transfer) CETP inhibitor scaffold containing an oxazolidinone core.

  DOI：

  10.1021/ml100309n

文献信息

• [EN] CETP INHIBITORS<br/>[FR] INHIBITEURS DE LA CETP
  申请人：MERCK & CO INC

  公开号：WO2006014357A1

  公开（公告）日：2006-02-09

  Compounds having the structures of Formula I, including pharmaceutically acceptable salts of the compounds, are CETP inhibitors, and are useful for raising HDL-cholesterol, reducing LDL-cholesterol, and for treating or preventing atherosclerosis: In the compounds of Formula I, B or R2 is a phenyl group which has an ortho aryl, heterocyclic, benzoheterocyclic or benzocycloalky substituent, and one other position on the 5-membered ring has an aromatic, heterocyclic, cycloalkyl, benzoheterocyclic or benzocycloalky substituent connected directly to the ring or attached to the ring through a -CH2-.

  具有公式I结构的化合物，包括这些化合物的药用盐，是CETP抑制剂，可用于提高HDL-胆固醇，降低LDL-胆固醇，并用于治疗或预防动脉粥样硬化：在公式I的化合物中，B或R2是具有邻位芳基、杂环、苯并杂环或苯环烷基取代基的苯基，而5-成员环的另一个位置具有直接连接到环或通过-CH2-连接到环的芳基、杂环、环烷基、苯并杂环或苯环烷基取代基。
• Discovery of Substituted Biphenyl Oxazolidinone Inhibitors of Cholesteryl Ester Transfer Protein
  作者：Christopher F. Thompson、Amjad Ali、Nazia Quraishi、Zhijian Lu、Milton L. Hammond、Peter J. Sinclair、Matt S. Anderson、Suzanne S. Eveland、Qiu Guo、Sheryl A. Hyland、Denise P. Milot、Carl P. Sparrow、Samuel D. Wright

  DOI：10.1021/ml100309n

  日期：2011.6.9

  Recently, there has been a strong interest in the ability to increase levels of high density lipoprotein-cholesterol (HDL-C). This interest stems from the hypothesis that such an elevation in HDL-C will decrease the likelihood of cardiovascular disease. Inhibition of cholesteryl ester transfer protein (CETP) has been shown to elevate HDL-C levels in human subjects. This letter describes the discovery of a novel and potent (<100 nM IC(50) for the inhibition of CE transfer) CETP inhibitor scaffold containing an oxazolidinone core.