2-(4-benzyloxyphenoxy)propane-1,3-diol | 1204483-47-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-benzyloxyphenoxy)propane-1,3-diol
• 英文别名: 2-(4-phenylmethoxyphenoxy)propane-1,3-diol
• CAS: 1204483-47-5
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: JCIUKNNQFRUHQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-benzyloxyphenoxy)propane-1,3-diol 在 10% palladium on activated carbon 、 氢气 、 caesium carbonate 、 对甲苯磺酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0~60.0 ℃ 、300.01 kPa 条件下， 反应 6.0h， 生成 trans-N-{3-[5-(4-cyclopentyloxyphenoxy)[1,3]dioxan-2-yl]propyl}acetamide
  参考文献：
  名称：

  Identification and Synthesis of Novel Inhibitors of Acetyl-CoA Carboxylase with in Vitro and in Vivo Efficacy on Fat Oxidation

  摘要：

  Acetyl CoA carboxylase isoforms 1 and 2 (ACC1/2) are key enzymes of fat utilization and their inhibition is considered to improve aspects of the metabolic syndrome. To identify pharmacological inhibitors of ACC1/2, a high throughput screen was performed which resulted in the identification of the lead compound 3 (Gargazanli, G.; Lardenois, P.; Frost, J.; George, P. Patent WO9855474 A1, 1998) as a moderate selective ACC2 inhibitor. Optimization of 3 led to 4m (Zoller, G.; Schmoll, D.; Mueller, M.; Haschke, G.; Focken, I. Patent WO2010003624 A2, 2010) as a submicromolar dual ACC1/2 inhibitor of the rat and human isoforms. 4m possessed favorable pharmacokinetic parameters. This compound stimulated fat oxidation in vivo and reduced plasma triglyceride levels in a rodent model after subchronic administration. 4m is a suitable tool compound for the elucidation of the pharmacological potential of ACC1/2 inhibition.

  DOI：

  10.1021/jm101179e
• 作为产物：
  描述：

  dimethyl 2-(4-benzyloxyphenoxy)malonate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以25%的产率得到2-(4-benzyloxyphenoxy)propane-1,3-diol
  参考文献：
  名称：

  Identification and Synthesis of Novel Inhibitors of Acetyl-CoA Carboxylase with in Vitro and in Vivo Efficacy on Fat Oxidation

  摘要：

  Acetyl CoA carboxylase isoforms 1 and 2 (ACC1/2) are key enzymes of fat utilization and their inhibition is considered to improve aspects of the metabolic syndrome. To identify pharmacological inhibitors of ACC1/2, a high throughput screen was performed which resulted in the identification of the lead compound 3 (Gargazanli, G.; Lardenois, P.; Frost, J.; George, P. Patent WO9855474 A1, 1998) as a moderate selective ACC2 inhibitor. Optimization of 3 led to 4m (Zoller, G.; Schmoll, D.; Mueller, M.; Haschke, G.; Focken, I. Patent WO2010003624 A2, 2010) as a submicromolar dual ACC1/2 inhibitor of the rat and human isoforms. 4m possessed favorable pharmacokinetic parameters. This compound stimulated fat oxidation in vivo and reduced plasma triglyceride levels in a rodent model after subchronic administration. 4m is a suitable tool compound for the elucidation of the pharmacological potential of ACC1/2 inhibition.

  DOI：

  10.1021/jm101179e

文献信息

• HETEROCYCLIC COMPOUNDS, PROCESSES FOR THEIR PREPARATION, MEDICAMENTS COMPRISING THESE COMPOUNDS, AND THE USE THEREOF
  申请人：Zoller Gerhard

  公开号：US20110183998A1

  公开（公告）日：2011-07-28

  Heterocyclic derivatives, processes for their preparation, medicaments comprising these compounds, and the use thereof. The invention relates to compounds of the formula I in which the radicals R1, R2, R3, R4, W, A, B, D, E, G, L, M, R, T and Y have the stated meanings, and to the physiologically tolerated salts thereof. The compounds are suitable for example for the treatment of the metabolic syndrome, insulin resistance, obesity and diabetes.

  杂环衍生物、其制备方法、包含这些化合物的药物和其用途。本发明涉及式I中的化合物，其中基团R1、R2、R3、R4、W、A、B、D、E、G、L、M、R、T和Y具有所述的含义，并且其生理上可耐受的盐。该化合物适用于例如代谢综合征、胰岛素抵抗、肥胖和糖尿病的治疗。
• Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof
  申请人：Zoller Gerhard

  公开号：US08470841B2

  公开（公告）日：2013-06-25

  Heterocyclic derivatives, processes for their preparation, medicaments comprising these compounds, and the use thereof. The invention relates to compounds of the formula I in which the radicals R1, R2, R3, R4, W, A, B, D, E, G, L, M, R, T and Y have the stated meanings, and to the physiologically tolerated salts thereof. The compounds are suitable for example for the treatment of the metabolic syndrome, insulin resistance, obesity and diabetes.

  杂环衍生物，其制备方法，包含这些化合物的药物和其用途。本发明涉及式I的化合物，其中基团R1，R2，R3，R4，W，A，B，D，E，G，L，M，R，T和Y具有所述的含义，并且其生理耐受盐。这些化合物适用于例如治疗代谢综合征，胰岛素抵抗，肥胖和糖尿病。
• [EN] HETEROCYCLIC COMPOUNDS, PROCESSES FOR THEIR PREPARATION, MEDICAMENTS COMPRISING THESE COMPOUNDS, AND THE USE THEREOF<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES, LEURS PROCÉDÉS DE PRÉPARATION, MÉDICAMENTS COMPRENANT LESDITS COMPOSÉS ET LEUR UTILISATION
  申请人：SANOFI AVENTIS

  公开号：WO2010003624A3

  公开（公告）日：2010-04-22
• US8470841B2
  申请人：——

  公开号：US8470841B2

  公开（公告）日：2013-06-25
• Identification and Synthesis of Novel Inhibitors of Acetyl-CoA Carboxylase with in Vitro and in Vivo Efficacy on Fat Oxidation
  作者：Stefanie Keil、Marco Müller、Gerhard Zoller、Guido Haschke、Katrin Schroeter、Maike Glien、Sven Ruf、Ingo Focken、Andreas W. Herling、Dieter Schmoll

  DOI：10.1021/jm101179e

  日期：2010.12.23

  Acetyl CoA carboxylase isoforms 1 and 2 (ACC1/2) are key enzymes of fat utilization and their inhibition is considered to improve aspects of the metabolic syndrome. To identify pharmacological inhibitors of ACC1/2, a high throughput screen was performed which resulted in the identification of the lead compound 3 (Gargazanli, G.; Lardenois, P.; Frost, J.; George, P. Patent WO9855474 A1, 1998) as a moderate selective ACC2 inhibitor. Optimization of 3 led to 4m (Zoller, G.; Schmoll, D.; Mueller, M.; Haschke, G.; Focken, I. Patent WO2010003624 A2, 2010) as a submicromolar dual ACC1/2 inhibitor of the rat and human isoforms. 4m possessed favorable pharmacokinetic parameters. This compound stimulated fat oxidation in vivo and reduced plasma triglyceride levels in a rodent model after subchronic administration. 4m is a suitable tool compound for the elucidation of the pharmacological potential of ACC1/2 inhibition.