6,6-dimethyl-7-(tetrahydropyran-2-yloxy)-heptanoic acid [5,5-dimethyl-6-(tetrahydropyran-2-yloxy)-hexyl]-amide | 615287-98-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6,6-dimethyl-7-(tetrahydropyran-2-yloxy)-heptanoic acid [5,5-dimethyl-6-(tetrahydropyran-2-yloxy)-hexyl]-amide
• 英文别名: 6,6-Dimethyl-7-(tetrahydropyran-2-yloxy)-heptanoic acid [5,5-dimethyl-6-(tetrahydro-pyran-2-yloxy)-hexyl]-amide；N-[5,5-dimethyl-6-(oxan-2-yloxy)hexyl]-6,6-dimethyl-7-(oxan-2-yloxy)heptanamide
• CAS: 615287-98-4
• 化学式: C₂₇H₅₁NO₅
• 分子量: 469.706
• InChiKey: TXTLEOGMROZUAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,6-dimethyl-7-(tetrahydropyran-2-yloxy)-heptanoic acid [5,5-dimethyl-6-(tetrahydropyran-2-yloxy)-hexyl]-amide 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以85%的产率得到7-hydroxy-6,6-dimethylheptanoic acid (6-hydroxy-5,5-dimethylhexyl)-amide
  参考文献：
  名称：

  Functionalized long chain derivatives as acyl coenzyme-A mimics, compositions thereof, and methods of cholesterol management and related uses

  摘要：

  该发明涉及新型酰辅酶A类似物，包含酮化合物的组合物，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，包括给予含有酮化合物的组合物。该发明的酰辅酶A类似物、组合物和方法也适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、细菌感染和阳痿。在某些实施例中，该发明的酰辅酶A类似物、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。

  公开号：

  US20030236212A1
• 作为产物：
  描述：

  6,6-dimethyl-7-(tetrahydropyran-2-yloxy)-heptanonitrile 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 76.0h， 生成 6,6-dimethyl-7-(tetrahydropyran-2-yloxy)-heptanoic acid [5,5-dimethyl-6-(tetrahydropyran-2-yloxy)-hexyl]-amide
  参考文献：
  名称：

  Influence of Various Central Moieties on the Hypolipidemic Properties of Long Hydrocarbon Chain Diols and Diacids

  摘要：

  A series of long (11-15) hydrocarbon chain diols and diacids with various central functional groups and terminal gem-dimethyl or -methyl/aryl substituents was synthesized and evaluated in both in vivo and in vitro assays for its 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 obese female Zucker fatty rats, Crl:(ZUC)-faBR. The most active compounds were hydroxyl-substituted symmetrical diacids and diols with a 13-atom chain and terminal gem-dimethyl substituents. Furthermore, biological activity was enhanced by central substitution with O, C=O, S, S=O compared to the methylene analogues and was diminished for compounds with central functional groups such as carbamate, ester, urea, acetylmethylene, and hydroxymethylene.

  DOI：

  10.1021/jm050650j

文献信息

• Functionalized long chain derivatives as acyl coenzyme-A mimics, compositions thereof, and methods of cholesterol management and related uses
  申请人：——

  公开号：US20030236212A1

  公开（公告）日：2003-12-25

  The invention relates to novel Acyl coenzyme-A mimics, compositions comprising ketone compounds, and methods useful for treating and preventing cardiovascular diseases, dyslipidemias, dysproteinemias, and glucose metabolism disorders comprising administering a composition comprising a ketone compound. The Acyl coenzyme-A mimics, 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, bacterial infection and impotence. In certain embodiments, the Acyl coenzyme-A mimics, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.

  该发明涉及新型酰辅酶A类似物，包含酮化合物的组合物，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，包括给予含有酮化合物的组合物。该发明的酰辅酶A类似物、组合物和方法也适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、细菌感染和阳痿。在某些实施例中，该发明的酰辅酶A类似物、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。
• Influence of Various Central Moieties on the Hypolipidemic Properties of Long Hydrocarbon Chain Diols and Diacids
  作者：Daniela C. Oniciu、Jean-Louis H. Dasseux、Jing Yang、Ralf Mueller、Emil Pop、Anna Denysenko、Caiming Duan、Tian-Bao Huang、Lianhao Zhang、Brian R. Krause、Sandra L. Drake、Narendra Lalwani、Clay T. Cramer、Brian Goetz、Michael E. Pape、Andrew McKee、Gregory J. Fici、Janell M. Lutostanski、Stephen C. Brown、Charles L. Bisgaier

  DOI：10.1021/jm050650j

  日期：2006.1.1

  A series of long (11-15) hydrocarbon chain diols and diacids with various central functional groups and terminal gem-dimethyl or -methyl/aryl substituents was synthesized and evaluated in both in vivo and in vitro assays for its 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 obese female Zucker fatty rats, Crl:(ZUC)-faBR. The most active compounds were hydroxyl-substituted symmetrical diacids and diols with a 13-atom chain and terminal gem-dimethyl substituents. Furthermore, biological activity was enhanced by central substitution with O, C=O, S, S=O compared to the methylene analogues and was diminished for compounds with central functional groups such as carbamate, ester, urea, acetylmethylene, and hydroxymethylene.