5-(5-hydroxy-4-methyl-4-phenylpentyloxy)-2-methyl-2-phenylpentan-1-ol

• 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-(5-hydroxy-4-methyl-4-phenylpentyloxy)-2-methyl-2-phenylpentan-1-ol
• 英文别名: 5-(5-hydroxy-4-methyl-4-phenylpentoxy)-2-methyl-2-phenylpentan-1-ol
• 化学式: C₂₄H₃₄O₃
• 分子量: 370.532
• InChiKey: UKNKRMSLEXHXAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(3-羟基丙氧基)丙-1-醇 在 lithium aluminium tetrahydride 、 三溴化磷 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正庚烷 、 乙基苯 为溶剂， 反应 1.5h， 生成 5-(5-hydroxy-4-methyl-4-phenylpentyloxy)-2-methyl-2-phenylpentan-1-ol
  参考文献：
  名称：

  Long Hydrocarbon Chain Ether Diols and Ether Diacids That Favorably Alter Lipid Disorders in Vivo

  摘要：

  Long hydrocarbon chain ethers with bis-terminal hydroxyl or carboxyl groups have been synthesized and evaluated for their potential to favorably alter lipid disorders including metabolic syndrome. Compounds were assessed for their effects on the de novo incorporation of radiolabeled acetate into lipids in primary cultures of rat hepatocytes as well as for their effects on lipid and glycemic variables in female obese Zucker fatty rats following 1 and 2 weeks of daily oral administration. The most active compounds were found to be symmetrical with four to five methylene groups separating the central ether functionality and the gem dimethyl or methyl/aryl substituents. Biological activity was found to be greatest for tetramethyl-substituted ether diols (e.g., 28 and 31), while bis(arylmethyl) derivatives (e.g., 10, 11, and 27), diethers (e.g., 49, 50, and 56), and diphenyl ethers (e.g., 35 and 36) were the least active. For the most biologically active compound 28, we observed as much as a 346% increase in serum HDL-cholesterol and a 71% reduction in serum triglycerides at the highest dose administered (100 mg/kg) after 2 weeks of treatment. For compound 31 we observed a 69% reduction in non-HDL-cholesterol, accompanied by a 131% increase in HDL-cholesterol and an 84% reduction in serum triglycerides under the same treatment conditions.

  DOI：

  10.1021/jm0400395

文献信息

• Ether compounds and compositions for cholesterol management and related uses
  申请人：——

  公开号：US20040192771A1

  公开（公告）日：2004-09-30

  The present invention relates to novel ether compounds, compositions comprising ether compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.

  本发明涉及新型醚化合物、含有醚化合物的组合物，以及用于治疗和预防心血管疾病、血脂异常、蛋白异常和葡萄糖代谢紊乱的方法，包括给予含有醚化合物的组合物。该发明的化合物、组合物和方法还可用于治疗和预防阿尔茨海默病、综合征X、过氧化物酶体增殖子活化受体相关疾病、败血症、血栓性疾病、肥胖、胰腺炎、高血压、肾脏疾病、癌症、炎症和阳痿。在某些实施方式中，该发明的化合物、组合物和方法可与其他治疗药物（如降胆固醇和降血糖药物）联合治疗。
• [EN] ETHER COMPOUNDS AND COMPOSITIONS FOR CHOLESTEROL MANAGEMENT AND RELATED USES<br/>[FR] COMPOSES D'ETHER ET COMPOSITIONS POUR LE CONTROLE DE CHOLESTEROL ET UTILISATIONS ASSOCIEES
  申请人：ESPERION THERAPEUTICS INC

  公开号：WO2005068410A1

  公开（公告）日：2005-07-28

  The present invention relates to novel ether compounds, compositions comprising ether compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising an ether compound. The compounds, compositions, and methods of the invention are also useful for treating and preventing Alzheimer's Disease, Syndrome X, peroxisome proliferator activated receptor-related disorders, septicemia, thrombotic disorders, obesity, pancreatitis, hypertension, renal disease, cancer, inflammation, and impotence. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.

  本发明涉及新型醚化合物、包含醚化合物的组合物以及用于治疗和预防心血管疾病、血脂异常、蛋白异常和葡萄糖代谢紊乱的方法，包括给予含有醚化合物的组合物。该发明的化合物、组合物和方法还可用于治疗和预防阿尔茨海默病、X综合征、过氧化物酶体增殖激活受体相关疾病、败血症、血栓性疾病、肥胖、胰腺炎、高血压、肾脏疾病、癌症、炎症和阳痿。在某些实施方式中，该发明的化合物、组合物和方法可与其他治疗药物（如降胆固醇和降血糖药物）联合治疗时使用。
• Long Hydrocarbon Chain Ether Diols and Ether Diacids That Favorably Alter Lipid Disorders in Vivo
  作者：Ralf Mueller、Jing Yang、Caiming Duan、Emil Pop、Lian Hao Zhang、Tian-Bao Huang、Anna Denisenko、Olga V. Denisko、Daniela C. Oniciu、Charles L. Bisgaier、Michael E. Pape、Catherine Delaney Freiman、Brian Goetz、Clay T. Cramer、Krista L. Hopson、Jean-Louis H. Dasseux

  DOI：10.1021/jm0400395

  日期：2004.10.1

  Long hydrocarbon chain ethers with bis-terminal hydroxyl or carboxyl groups have been synthesized and evaluated for their potential to favorably alter lipid disorders including metabolic syndrome. Compounds were assessed for their effects on the de novo incorporation of radiolabeled acetate into lipids in primary cultures of rat hepatocytes as well as for their effects on lipid and glycemic variables in female obese Zucker fatty rats following 1 and 2 weeks of daily oral administration. The most active compounds were found to be symmetrical with four to five methylene groups separating the central ether functionality and the gem dimethyl or methyl/aryl substituents. Biological activity was found to be greatest for tetramethyl-substituted ether diols (e.g., 28 and 31), while bis(arylmethyl) derivatives (e.g., 10, 11, and 27), diethers (e.g., 49, 50, and 56), and diphenyl ethers (e.g., 35 and 36) were the least active. For the most biologically active compound 28, we observed as much as a 346% increase in serum HDL-cholesterol and a 71% reduction in serum triglycerides at the highest dose administered (100 mg/kg) after 2 weeks of treatment. For compound 31 we observed a 69% reduction in non-HDL-cholesterol, accompanied by a 131% increase in HDL-cholesterol and an 84% reduction in serum triglycerides under the same treatment conditions.