N-(3,4-methylenedioxyphenyl)-N'-phenylguanidine hydrochloride | 1615250-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N-(3,4-methylenedioxyphenyl)-N'-phenylguanidine hydrochloride
• 英文别名: 1-(1,3-Benzodioxol-5-yl)-2-phenylguanidine;hydrochloride；1-(1,3-benzodioxol-5-yl)-2-phenylguanidine;hydrochloride
• CAS: 1615250-48-0
• 化学式: C₁₄H₁₃N₃O₂*ClH
• 分子量: 291.737
• InChiKey: PEUSQEIXVSXYLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68.9
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 Amberlite resin (Cl- form) 作用下， 以 水 为溶剂， 反应 16.0h， 以208 mg的产率得到N-(3,4-methylenedioxyphenyl)-N'-phenylguanidine hydrochloride
  参考文献：
  名称：

  Guanidine-based α2-adrenoceptor ligands: Towards selective antagonist activity

  摘要：

  Depression has been linked to a selective increase in the high affinity conformation of the alpha(2)-adrenergic autoreceptors (alpha 2-ARs) in the human brain as well as to an overexpression of alpha 2-ARs in the hippocampus and cerebral cortex. Thus, the development of novel alpha 2-AR antagonists represents an attractive source of new antidepressants. This paper describes the design, synthesis and pharmacological evaluation of 30 new guanidinium and 2-iminoimidazolidinium as potential alpha 2-AR antagonists. In order to design this new series of alpha 2-AR antagonists, a pharmacophore model was developed using the GALAHAD software. This study suggested that increased substitution in the space surrounding the cationic guanidine moiety might lead selectively to antagonist activity. Following the preparation of compounds incorporating this feature and competitive radioligand binding, [S-35]GTP gamma S functional assays revealed that this structural modification affords exclusively alpha 2-AR antagonists, in contrast with the analogous unsubstituted compounds in which a mixture of antagonist/agonist activities was previously observed. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.057

文献信息

• Guanidine-based α2-adrenoceptor ligands: Towards selective antagonist activity
  作者：Daniel H. O'Donovan、Carolina Muguruza、Luis F. Callado、Isabel Rozas

  DOI：10.1016/j.ejmech.2014.05.057

  日期：2014.7

  Depression has been linked to a selective increase in the high affinity conformation of the alpha(2)-adrenergic autoreceptors (alpha 2-ARs) in the human brain as well as to an overexpression of alpha 2-ARs in the hippocampus and cerebral cortex. Thus, the development of novel alpha 2-AR antagonists represents an attractive source of new antidepressants. This paper describes the design, synthesis and pharmacological evaluation of 30 new guanidinium and 2-iminoimidazolidinium as potential alpha 2-AR antagonists. In order to design this new series of alpha 2-AR antagonists, a pharmacophore model was developed using the GALAHAD software. This study suggested that increased substitution in the space surrounding the cationic guanidine moiety might lead selectively to antagonist activity. Following the preparation of compounds incorporating this feature and competitive radioligand binding, [S-35]GTP gamma S functional assays revealed that this structural modification affords exclusively alpha 2-AR antagonists, in contrast with the analogous unsubstituted compounds in which a mixture of antagonist/agonist activities was previously observed. (C) 2014 Elsevier Masson SAS. All rights reserved.