methyl 2-(2-cyclopropylphenoxy)propanoate | 1197813-10-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-(2-cyclopropylphenoxy)propanoate
• 英文别名: 2-(2-cyclopropylphenoxy)propionic acid methyl ester
• CAS: 1197813-10-7
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: CZEFMFNIWAPEIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-cyclopropylphenoxy)propanoate 在 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以76 %的产率得到2-(2-cyclopropylphenoxy)propanoic acid
  参考文献：
  名称：

  WO2023/187677

  摘要：

  公开号：
• 作为产物：
  描述：

  2-溴丙酸甲酯 、 2-环丙基苯酚 在 potassium carbonate 作用下， 以 乙二醇二甲醚 为溶剂， 以75%的产率得到methyl 2-(2-cyclopropylphenoxy)propanoate
  参考文献：
  名称：

  Might Adrenergic α_2C-Agonists/α_2A-Antagonists Become Novel Therapeutic Tools for Pain Treatment with Morphine?

  摘要：

  The imidazoline nucleus linked in position 2 via an oxyethylene bridge to a phenyl ring carrying an ortho substituent of moderate steric bulk provided alpha(2)-adrenergic (AR) ligands endowed with significant alpha(2C)-agonism/alpha(2A)-antagonism. Similar behavior was displayed by cirazoline (12). For their positive morphine analgesia modulation (due to alpha(2C)-AR stimulation) and sedation overcoming (due to alpha(2A)-AR antagonism), 8 and 11 might be useful as adjuvant agents in the management of pain with morphine.

  DOI：

  10.1021/jm901262f

文献信息

• Synergic stimulation of serotonin 5-HT1A receptor and α2-adrenoceptors for neuropathic pain relief: Preclinical effects of 2-substituted imidazoline derivatives
  作者：Lorenzo Di Cesare Mannelli、Carla Ghelardini、Laura Micheli、Fabio Del Bello、Mario Giannella、Alessandro Piergentili、Maria Pigini、Wilma Quaglia

  DOI：10.1016/j.ejphar.2017.06.023

  日期：2017.9

  Neuropathic pain affects millions of people causing disability and impairing quality of life. Commonly used analgesics are generally characterized by limited therapeutic outcomes. The serotonin 5-HT1A receptor and the alpha(2) adrenergic receptors are involved in central nociceptive mechanisms with a pivotal role in the inhibitory descending pain pathway. Since their stimulation may modulate the nervous signaling altered by neuropathies, the purpose of the present research is the study of the combined activation of 5-HT1A and alpha(2) receptors by rationally designed imidazoline ligands ((S)-(-)-1 and 2-5) in a rat model of neuropathic pain (chronic constriction injury - CCI). On day 14 after nerve damage, the acute administration per os (p.o.) of low doses of (S)-(-)-1 (0.1-1 mg/kg) was able to significantly increase the pain threshold to mechanical noxious stimuli for more than 1 h. (S)-(-)-1 efficacy was confirmed by the decrease of spontaneous pain evaluated as hind limb weight bearing alterations. The clinically-used compound gabapentin (100 mg/kg p.o.) induced a pain relieving effect similar to (S)-(-)-1 administered at 100 fold lower dose. In the same model, the selected analogues, compounds 2-5 (1 mg/kg p.o.) were effective 30 min after administration. In particular, 5 fully reverted the CCI-induced hypersensitivity. The pain relieving activity of 5 was significantly prevented by the selective 5-HTSA receptor antagonist WAY 100635 (1 mg/kg intraperitoneally, i,p.) and, at a lesser extent, by the alpha(2) antagonist yohimbine (3 mg/kg i.p.). A novel pharmacodynamic approach to the treatment of neuropathic pain is presented.
• Might Adrenergic α_2C-Agonists/α_2A-Antagonists Become Novel Therapeutic Tools for Pain Treatment with Morphine?
  作者：Claudia Cardinaletti、Laura Mattioli、Francesca Ghelfi、Fabio Del Bello、Mario Giannella、Ariana Bruzzone、Hervé Paris、Marina Perfumi、Alessandro Piergentili、Wilma Quaglia、Maria Pigini

  DOI：10.1021/jm901262f

  日期：2009.11.26

  The imidazoline nucleus linked in position 2 via an oxyethylene bridge to a phenyl ring carrying an ortho substituent of moderate steric bulk provided alpha(2)-adrenergic (AR) ligands endowed with significant alpha(2C)-agonism/alpha(2A)-antagonism. Similar behavior was displayed by cirazoline (12). For their positive morphine analgesia modulation (due to alpha(2C)-AR stimulation) and sedation overcoming (due to alpha(2A)-AR antagonism), 8 and 11 might be useful as adjuvant agents in the management of pain with morphine.
• WO2023/187677
  申请人：——

  公开号：——

  公开（公告）日：——