(3,5-dimethyl-4-hydroxy-phenyl)-acetic acid methyl ester | 51511-17-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (3,5-dimethyl-4-hydroxy-phenyl)-acetic acid methyl ester
• 英文别名: methyl 2-(4-hydroxy-3,5-dimethylphenyl)acetate
• CAS: 51511-17-2
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: UCJBJPOAPYTDOA-UHFFFAOYSA-N

物化性质

• 沸点：
  296.2±35.0 °C(Predicted)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3,5-dimethyl-4-hydroxy-phenyl)-acetic acid methyl ester 在 copper(l) iodide 、 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 [4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-3,5-dimethyl-phenyl]-acetic acid
  参考文献：
  名称：

  Discovery of 2-[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydropyridazin-3-yloxy)phenyl]-3,5-dioxo-2,3,4,5-tetrahydro[1,2,4]triazine-6-carbonitrile (MGL-3196), a Highly Selective Thyroid Hormone Receptor β Agonist in Clinical Trials for the Treatment of Dyslipidemia

  摘要：

  The beneficial effects of thyroid hormone (TH) on lipid levels are primarily due to its action at the thyroid hormone receptor beta (THR-beta) in the liver, while adverse effects, including cardiac effects, are mediated by thyroid hormone receptor alpha (THR-alpha). A pyridazinone series has been identified that is significantly more THR-beta selective than earlier analogues. Optimization of this series by the addition of a cyanoazauracil substituent improved both the potency and selectivity and led to MGL-3196 (53), which is 28-fold selective for THR-beta over THR-alpha in a functional assay. Compound 53 showed outstanding safety in a rat heart model and was efficacious in a preclinical model at doses that showed no impact on the central thyroid axis. In reported studies in healthy volunteers, 53 exhibited an excellent safety profile and decreased LDL cholesterol (LDL-C) and triglycerides (TG) at once daily oral doses of 50 mg or higher given for 2 weeks.

  DOI：

  10.1021/jm4019299
• 作为产物：
  描述：

  4-[(二甲基氨基)甲基]-2,6-二甲苯酚 在 硫酸 、 potassium hydroxide 作用下， 以 乙二醇二甲醚 、 乙醚 、 乙醇 、 水 为溶剂， 反应 96.0h， 生成 (3,5-dimethyl-4-hydroxy-phenyl)-acetic acid methyl ester
  参考文献：
  名称：

  Discovery of 2-[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydropyridazin-3-yloxy)phenyl]-3,5-dioxo-2,3,4,5-tetrahydro[1,2,4]triazine-6-carbonitrile (MGL-3196), a Highly Selective Thyroid Hormone Receptor β Agonist in Clinical Trials for the Treatment of Dyslipidemia

  摘要：

  The beneficial effects of thyroid hormone (TH) on lipid levels are primarily due to its action at the thyroid hormone receptor beta (THR-beta) in the liver, while adverse effects, including cardiac effects, are mediated by thyroid hormone receptor alpha (THR-alpha). A pyridazinone series has been identified that is significantly more THR-beta selective than earlier analogues. Optimization of this series by the addition of a cyanoazauracil substituent improved both the potency and selectivity and led to MGL-3196 (53), which is 28-fold selective for THR-beta over THR-alpha in a functional assay. Compound 53 showed outstanding safety in a rat heart model and was efficacious in a preclinical model at doses that showed no impact on the central thyroid axis. In reported studies in healthy volunteers, 53 exhibited an excellent safety profile and decreased LDL cholesterol (LDL-C) and triglycerides (TG) at once daily oral doses of 50 mg or higher given for 2 weeks.

  DOI：

  10.1021/jm4019299

文献信息

• THYROID HORMONE ANALOGS
  申请人：Haynes Nancy-Ellen

  公开号：US20090005383A1

  公开（公告）日：2009-01-01

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as obesity, hyperlipidemia, hypercholesterolemia and diabetes and other related disorders and diseases, and may be useful for other diseases such as NASH, atherosclerosis, cardiovascular diseases, hypothyroidism, thyroid cancer and other disorders and diseases related thereto.

  本文提供了公式（I）的化合物，以及其药学上可接受的盐，其中取代基如说明书所披露的那样。这些化合物和含有它们的药物组合物对于治疗肥胖症、高脂血症、高胆固醇血症和糖尿病以及其他相关疾病和疾病非常有用，并且可能对于其他疾病，如NASH，动脉粥样硬化，心血管疾病，甲状腺功能减退症，甲状腺癌和其他相关的疾病和疾病也有用。
• Thyroid hormone analogs
  申请人：Haynes Nancy-Ellen

  公开号：US20070032494A1

  公开（公告）日：2007-02-08

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as obesity, hyperlipidemia, hypercholesterolemia and diabetes and other related disorders and diseases, and may be useful for other diseases such as NASH, atherosclerosis, cardiovascular diseases, hypothyroidism, thyroid cancer and other disorders and diseases related thereto.

  本文提供的化合物公式(I)及其药学上可接受的盐，其中取代基如规范中所述。这些化合物及其含有的药物组成物，可用于治疗肥胖症、高脂血症、高胆固醇血症、糖尿病和其他相关疾病，也可能对NASH、动脉粥样硬化、心血管疾病、甲状腺功能减退症、甲状腺癌和其他相关疾病有用。
• Hydroxychroman Derivatives As Engine Oil Antioxidants
  申请人：Crawley Seth L.

  公开号：US20130165355A1

  公开（公告）日：2013-06-27

  A lubricant and concentrate composition comprises a hydroxychroman derived antioxidant and a method for improving the performance of a lubricant composition, especially a lubricant composition for an internal combustion engine, comprising the use of a lubricant containing said antioxidant.

  一种润滑剂和浓缩物组合物包括一种来源于羟基香豆素的抗氧化剂，以及一种改善润滑剂组合物性能的方法，特别是用含有该抗氧化剂的润滑剂组合物。该润滑剂组合物适用于内燃机的润滑剂组合物。
• WO2007/9913
  申请人：——

  公开号：——

  公开（公告）日：——
• USRE046024E1
  申请人：——

  公开号：——

  公开（公告）日：——