2-(3,5-dichloro-4-hydroxyphenyl)ethanol | 115150-58-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(3,5-dichloro-4-hydroxyphenyl)ethanol
• 英文别名: 2,6-dichloro-4-(2-hydroxyethyl)phenol
• CAS: 115150-58-8
• 化学式: C₈H₈Cl₂O₂
• 分子量: 207.056
• InChiKey: HHBCXDGBMINMHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3,5-dichloro-4-hydroxyphenyl)ethanol 在 potassium tert-butylate 、 sodium acetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 48.0h， 生成 3,5-dichloro-4-((5-isopropyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy)phenylethyl acetate
  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-羟基苯乙酸甲酯 在 lithium aluminium tetrahydride 、 二异丁胺 、 磺酰氯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.25h， 生成 2-(3,5-dichloro-4-hydroxyphenyl)ethanol
  参考文献：
  名称：

  [EN] THYROID HORMONE RECEPTOR AGONISTS
  [FR] AGONISTES DU RÉCEPTEUR DES HORMONES THYROÏDIENNES

  摘要：

  本文提供了新型甲状腺激素受体（TR）激动剂，例如具有公式I、II或III的激动剂。还提供了制备新型TR激动剂的方法以及利用新型TR激动剂治疗由TR激动剂调节的疾病或紊乱的方法，例如NAFLD、NASH、糖尿病、高脂血症和/或高胆固醇血症。

  公开号：

  WO2020073974A1

文献信息

• New halometabolites from Caldariomyces fumago
  作者：Maurice C.R. Franssen、Maarten A. Posthumus、Henk C. Van Der Plas

  DOI：10.1016/0031-9422(88)80280-2

  日期：——

  Abstract The culture medium of the mould Caldariomyces fumago was extracted with three organic solvents and the extracts were analysed by GC-MS. Twelve halogen-containing metabolites were found in the dichloromethane extract. Seven of these compounds were sufficiently abundant to allow the identification of the new halometabolites, 2,2-dichloroethanol, 1,3-dichloropropanol-2, 1,1,3-trichloropropanol-2

  摘要 采用三种有机溶剂对霉菌Caldariomyces fumago 培养基进行提取，并用GC-MS 进行分析。在二氯甲烷提取物中发现了 12 种含卤素的代谢物。其中 7 种化合物的丰度足以鉴定新的卤代代谢物：2,2-二氯乙醇、1,3-二氯丙醇-2、1,1,3-三氯丙醇-2、1,1,3,3-四氯丙醇- 2、2-(3-氯-4-羟基苯基)乙醇和2-(3,5-二氯-4-羟基苯基)乙醇以及众所周知的caldariomycin (2,2-dichloro-1 S ,3 S -二羟基环戊烷）。讨论了它们可能的生物合成途径和对 Caldariomyces 卤化酶氯过氧化物酶反应机制的影响。
• 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。
• WO2006/92268
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2007/9913
  申请人：——

  公开号：——

  公开（公告）日：——