ethyl 5-bromo-2-methyl-2-phenylpentanoate | 412937-84-9

• 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: ethyl 5-bromo-2-methyl-2-phenylpentanoate
• 英文别名: 5-bromo-2-methyl-2-phenyl-pentanoic acid ethyl ester；Ethyl 5-bromo-2-methyl-2-phenyl-pentanoate
• CAS: 412937-84-9
• 化学式: C₁₄H₁₉BrO₂
• 分子量: 299.208
• InChiKey: NMMPIUGZSFYHRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 5-bromo-2-methyl-2-phenylpentanoate 在 sodium sulfide 、 锂硼氢 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 5-(5-Hydroxy-4-methyl-4-phenyl-pentylsulfanyl)-2-methyl-2-phenyl-pentan-1-ol
  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
• 作为产物：
  描述：

  苯乙酸乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 1.0h， 生成 ethyl 5-bromo-2-methyl-2-phenylpentanoate
  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

• [EN] SULFIDE AND DISULFIDE COMPOUNDS AND COMPOSITIONS FOR CHOLESTEROL MANAGEMENT AND RELATED USES<br/>[FR] COMPOSES SULFURES ET DISULFURES ET COMPOSITIONS POUR LE CONTROLE DE CHOLESTEROL ET UTILISATIONS ASSOCIEES
  申请人：ESPERION THERAPEUTICS INC

  公开号：WO2005068418A1

  公开（公告）日：2005-07-28

  The invention encompasses novel sulfide and disulfide compounds, compositions comprising sulfide and disulfide 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.

  该发明涵盖了新型硫化物和二硫化物化合物，包括硫化物和二硫化物化合物的组合物，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。在某些实施例中，该发明的化合物、组合物和方法可与其他治疗药物联合治疗，如降胆固醇和降血糖药物。
• Urea and thiourea compounds and compositions for cholesterol management and related uses
  申请人：Dasseux Henri Jean-Louis

  公开号：US20050192347A1

  公开（公告）日：2005-09-01

  The present invention relates to novel urea and thiourea compounds, compositions comprising urea or thiourea compounds, and methods useful for treating and preventing aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, enhancing bile production, enhancing reverse lipid transport, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, modulating C reactive protein, obesity, oxysterol elimination in bile, pancreatitis, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), a thrombotic disorder, gastrointestinal disease, irritable bowel syndrome (IBS), inflammatory bowel disease (e.g., Crohn's Disease, ulcerative colitis), arthritis (e.g., rheumatoid arthritis, osteoarthritis), autoimmune disease (e.g., systemic lupus erythematosus), scleroderma, ankylosing spondylitis, gout and pseudogout, muscle pain: polymyositis/polymyalgia rheumatica/fibrositis; infection and arthritis, juvenile rheumatoid arthritis, tendonitis, bursitis and other soft tissue rheumatism. 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.

  本发明涉及新型尿素和硫脲化合物，包含尿素或硫脲化合物的组合物，以及用于治疗和预防衰老、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、血脂异常、脂蛋白异常、增强胆汁产生、增强逆向脂质转运、高血压、阳痿、炎症、胰岛素抵抗、胆汁中脂质的清除、调节C反应蛋白、肥胖、胆汁中氧固醇的清除、胰腺炎、帕金森病、过氧化物酶体增殖激活受体相关的疾病、胆汁中磷脂的清除、肾脏疾病、败血症、代谢综合征疾病（如X综合症）、血栓性疾病、胃肠道疾病、肠易激综合症（IBS）、炎症性肠病（如克罗恩病、溃疡性结肠炎）、关节炎（如类风湿性关节炎、骨关节炎）、自身免疫疾病（如系统性红斑狼疮）、硬皮病、强直性脊柱炎、痛风和假性痛风、肌肉疼痛：多发性肌炎/多发性肌痛症/纤维炎；感染和关节炎、儿童类风湿性关节炎、肌腱炎、滑囊炎和其他软组织风湿病的方法。在某些实施方式中，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）联合治疗。
• [EN] UREA AND THIOUREA COMPOUNDS AND COMPOSITIONS FOR CHOLESTEROL MANAGEMENT AND RELATED USES<br/>[FR] COMPOSES D'UREE ET DE THIOUREE ET COMPOSITIONS POUR LA GESTION DE CHOLESTEROL ET UTILISATIONS ASSOCIEES
  申请人：ESPERION THERAPEUTICS INC

  公开号：WO2005068420A1

  公开（公告）日：2005-07-28

  The present invention relates to novel urea and thiourea compounds, compositions comprising urea or thiourea compounds, and methods useful for treating and preventing aging, Alzheimer’s Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, enhancing bile production, enhancing reverse lipid transport, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, modulating C reactive protein, obesity, oxysterol elimination in bile, pancreatitis, Parkinson’s disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), a thrombotic disorder, gastrointestinal disease , irritable bowel syndrome (IBS), inflammatory bowel disease (e.g., Crohn’s Disease, ulcerative colitis), arthritis (e.g., rheumatoid arthritis, osteoarthritis), autoimmune disease (e.g., systemic lupus erythematosus), scleroderma, ankylosing spondylitis, gout and pseudogout, muscle painö polymyositis/polymyogia rheumatica/bifrositis; infection and arthritis, juvenile rheumatoid arthritis, tendonitis, bursitis and other soft tissue rheumatism. 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.

  本发明涉及新型脲和硫脲化合物，包含脲或硫脲化合物的组合物，以及用于治疗和预防衰老、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、葡萄糖代谢紊乱、血脂异常、脂蛋白异常、增强胆汁产生、增强逆向脂质转运、高血压、阳痿、炎症、胰岛素抵抗、胆汁中脂质的消除、调节C反应蛋白、肥胖、胆汁中氧化固醇的消除、胰腺炎、帕金森病、过氧化物酶体增殖物活化受体相关疾病、胆汁中磷脂的消除、肾脏疾病、败血症、代谢综合症疾病（例如综合征X）、血栓性疾病、胃肠疾病、肠易激综合症（IBS）、炎症性肠病（例如克罗恩病、溃疡性结肠炎）、关节炎（例如类风湿关节炎、骨关节炎）、自身免疫性疾病（例如系统性红斑狼疮）、硬皮病、强直性脊柱炎、痛风和假性痛风、肌肉疼痛性多发性肌炎/多发性肌痛/双肌炎；感染和关节炎、儿童类风湿关节炎、肌腱炎、滑囊炎和其他软组织风湿病。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）联合治疗。
• 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。