2,2,11,11-tetramethyl-7-oxododecanedioic acid 1-ethyl ester | 738606-50-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2,2,11,11-tetramethyl-7-oxododecanedioic acid 1-ethyl ester
• 英文别名: 12-ethoxy-2,2,11,11-tetramethyl-6,12-dioxododecanoic acid
• CAS: 738606-50-3
• 化学式: C₁₈H₃₂O₅
• 分子量: 328.449
• InChiKey: QAYXPZYSFZLUIY-UHFFFAOYSA-N

物化性质

• 沸点：
  457.1±30.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2,11,11-tetramethyl-7-oxododecanedioic acid 1-ethyl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以60%的产率得到2,2,11,11-tetramethyl-6-oxo-dodecanedioic acid
  参考文献：
  名称：

  Long Hydrocarbon Chain Keto Diols and Diacids that Favorably Alter Lipid Disorders in Vivo

  摘要：

  Keto-substituted hydrocarbons with 11 - 19 methylene and bis-terminal hydroxyl and carboxyl groups have been synthesized and evaluated in both in vivo and in vitro assays 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 obese female Zucker fatty rats [Crl:(ZUC)-faBRI following 1 and 2 weeks of oral administration. The most active compounds were found to be symmetrical with four to five methylene groups separating the central ketone functionality and the gem dimethyl or methyl/aryl substituents. Furthermore, biological activity was found to be greatest in both in vivo and in vitro assays for the tetramethyl-substituted keto diacids and diols (e.g., 10c, 10g, 14c), and the least active were shown to be the bis(arylmethyl) derivatives (e.g., 10e, 10f, 14f). Compound 14c dose-dependently elevated HDL-cholesterol, reduced triglycerides, and reduced NEFA, with a minimum effective dose of 30 mg/kg/day. Compound 10g dose-dependently modified non-HDL-cholesterol, triglycerides, and nonesterified fatty acids, with a minimum effective dose of 10 mg/kg/day. At this dose, compound 10g elevated HDL-cholesterol levels 2-3 times higher than pretreatment levels, and a dose-dependent reduction of fasting insulin and glucose levels was observed.

  DOI：

  10.1021/jm040006p
• 作为产物：
  描述：

  2H-吡喃,2-[(5-溴-2,2-二甲代戊基)氧代]四氢- 在 重铬酸吡啶 、 硫酸 、 四丁基碘化铵 、 sodium hydride 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 67.67h， 生成 2,2,11,11-tetramethyl-7-oxododecanedioic acid 1-ethyl ester
  参考文献：
  名称：

  Long Hydrocarbon Chain Keto Diols and Diacids that Favorably Alter Lipid Disorders in Vivo

  摘要：

  Keto-substituted hydrocarbons with 11 - 19 methylene and bis-terminal hydroxyl and carboxyl groups have been synthesized and evaluated in both in vivo and in vitro assays 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 obese female Zucker fatty rats [Crl:(ZUC)-faBRI following 1 and 2 weeks of oral administration. The most active compounds were found to be symmetrical with four to five methylene groups separating the central ketone functionality and the gem dimethyl or methyl/aryl substituents. Furthermore, biological activity was found to be greatest in both in vivo and in vitro assays for the tetramethyl-substituted keto diacids and diols (e.g., 10c, 10g, 14c), and the least active were shown to be the bis(arylmethyl) derivatives (e.g., 10e, 10f, 14f). Compound 14c dose-dependently elevated HDL-cholesterol, reduced triglycerides, and reduced NEFA, with a minimum effective dose of 30 mg/kg/day. Compound 10g dose-dependently modified non-HDL-cholesterol, triglycerides, and nonesterified fatty acids, with a minimum effective dose of 10 mg/kg/day. At this dose, compound 10g elevated HDL-cholesterol levels 2-3 times higher than pretreatment levels, and a dose-dependent reduction of fasting insulin and glucose levels was observed.

  DOI：

  10.1021/jm040006p

文献信息

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

  公开号：US20040198814A1

  公开（公告）日：2004-10-07

  The present invention relates to novel ketone compounds, 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 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.

  本发明涉及新型酮化合物、含有酮化合物的组合物，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。本发明的化合物、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、过氧化物酶体增殖物激活受体相关疾病、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。在某些实施例中，本发明的化合物、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）联合使用。
• [EN] KETONE COMPOUNDS AND COMPOSITIONS FOR CHOLESTEROL MANAGEMENT AND RELATED USES<br/>[FR] COMPOSES A FONCTION CETONE ET COMPOSITIONS POUR LE CONTROLE DE CHOLESTEROL ET UTILISATIONS ASSOCIEES
  申请人：ESPERION THERAPEUTICS INC

  公开号：WO2005068412A1

  公开（公告）日：2005-07-28

  The present invention relates to novel ketone compounds, 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 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.

  本发明涉及新型酮化合物、含有酮化合物的组合物，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。该发明的化合物、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、炎症和阳痿。在某些实施例中，该发明的化合物、组合物和方法还适用于与其他治疗药物联合治疗，如降胆固醇和降糖药物。
• Hydroxyl compounds and compositions for cholesterol management and related uses
  申请人：Dasseux Henri Jean-Louis

  公开号：US20050043278A1

  公开（公告）日：2005-02-24

  The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient. 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.

  本发明涉及新型羟基化合物、包含羟基化合物的组合物以及用于治疗和预防多种疾病和病症的方法，例如但不限于衰老、阿尔茨海默病、癌症、心血管疾病、糖尿病肾病、糖尿病视网膜病变、葡萄糖代谢紊乱、脂质代谢异常、高血压、阳痿、炎症、胰岛素抵抗、胆汁中脂质清除、肥胖、胆汁中氧化固醇清除、胰腺炎、帕金森病、过氧化物酶体增殖激活受体相关疾病、胆汁中磷脂清除、肾脏疾病、败血症、代谢综合征（例如X综合征）、血栓性疾病等。本发明的化合物和方法还可以用于调节C反应蛋白或增强患者的胆汁产生。在某些实施例中，本发明的化合物、组合物和方法与其他治疗剂（例如降胆固醇和降血糖药物）的联合治疗中有用。
• KETONE COMPOUNDS AND COMPOSITIONS FOR CHOLESTEROL MANAGEMENT AND RELATED USES
  申请人：Dasseux Henri Jean-Louis

  公开号：US20070149615A9

  公开（公告）日：2007-06-28

  The present invention relates to novel ketone compounds, 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 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.

  本发明涉及新型酮类化合物、包含酮类化合物的组合物以及用于治疗和预防心血管疾病、脂质代谢异常、蛋白质代谢异常和葡萄糖代谢紊乱的方法，其中包括给予含有酮类化合物的组合物。本发明的化合物、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、过氧化物酶体增殖物激活受体相关疾病、败血症、血栓性疾病、肥胖症、胰腺炎、高血压、肾脏疾病、癌症、炎症和阳痿。在某些实施例中，本发明的化合物、组合物和方法可与其他治疗剂（如降胆固醇和降血糖药物）联合治疗。
• HYDROXYL COMPOUNDS AND COMPOSITIONS FOR CHOLESTEROL MANAGEMENT AND RELATED USES
  申请人：Dasseux Henri Jean-Louis

  公开号：US20070179120A1

  公开（公告）日：2007-08-02

  The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient. 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.

  本发明涉及新型羟基化合物、包含羟基化合物的组合物以及用于治疗和预防各种疾病和病症的方法，例如但不限于衰老、阿尔茨海默病、癌症、心血管疾病、糖尿病肾病、糖尿病视网膜病变、葡萄糖代谢障碍、脂质代谢异常、高血压、阳痿、炎症、胰岛素抵抗、胆汁中脂质的排泄、肥胖症、胆汁中氧化固醇的排泄、胰腺炎、帕金森病、过氧化物酶体增殖物激活受体相关疾病、胆汁中磷脂的排泄、肾脏疾病、败血症、代谢综合征（例如X综合征）、血栓性疾病。本发明的化合物和方法还可用于调节C反应蛋白或增强患者的胆汁产生。在某些实施例中，本发明的化合物、组合物和方法可与其他治疗药物（例如降胆固醇和降血糖药物）联合使用。