ethyl 3-(2-hydroxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carboxylate | 1491063-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-(2-hydroxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carboxylate
• 英文别名: Ethyl 5-(2-hydroxyphenyl)-3-phenyl-3,4-dihydropyrazole-2-carboxylate；ethyl 5-(2-hydroxyphenyl)-3-phenyl-3,4-dihydropyrazole-2-carboxylate
• CAS: 1491063-49-0
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: HHYQMNSRTBZUSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲醛 在 potassium carbonate 、 sodium hydroxide 、 肼 作用下， 以 甲醇 为溶剂， 反应 72.5h， 生成 ethyl 3-(2-hydroxyphenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carboxylate
  参考文献：
  名称：

  Monoamine oxidase inhibitory activity of 3,5-biaryl-4,5-dihydro-1H-pyrazole-1-carboxylate derivatives

  摘要：

  Ethyl and phenyl carbamate derivatives of pyrazoline (3a-3h) were synthesized and tested for their MAO inhibitory activity. All the compounds were found to be selective towards MAO-A. Phenyl carbamates (3e-3h) were better than ethyl carbamates (3a-3d) and displayed the best selectivity index. Compound 3f (Ki(MAO-A); 4.96 +/- 0.21 nM) was found to be equally potent as that of standard drug, Moclobemide (Ki(MAO-A); 5.01 +/- 0.13 nM) but with best selectivity index (8.86 x 10-5). Molecular docking studies with R & S conformer of 3f revealed S-enantiomer is better than R-enantiomer as reported earlier by other groups. It is proposed that VdW's radii of the substitution (bulkiness) in ring B determine the potency of phenyl carbamates. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.010

文献信息

• Monoamine oxidase inhibitory activity of 3,5-biaryl-4,5-dihydro-1H-pyrazole-1-carboxylate derivatives
  作者：B. Vishnu Nayak、S. Ciftci-Yabanoglu、Surender Singh Jadav、Monika Jagrat、Barij N. Sinha、G. Ucar、Venkatesan Jayaprakash

  DOI：10.1016/j.ejmech.2013.09.010

  日期：2013.11

  Ethyl and phenyl carbamate derivatives of pyrazoline (3a-3h) were synthesized and tested for their MAO inhibitory activity. All the compounds were found to be selective towards MAO-A. Phenyl carbamates (3e-3h) were better than ethyl carbamates (3a-3d) and displayed the best selectivity index. Compound 3f (Ki(MAO-A); 4.96 +/- 0.21 nM) was found to be equally potent as that of standard drug, Moclobemide (Ki(MAO-A); 5.01 +/- 0.13 nM) but with best selectivity index (8.86 x 10-5). Molecular docking studies with R & S conformer of 3f revealed S-enantiomer is better than R-enantiomer as reported earlier by other groups. It is proposed that VdW's radii of the substitution (bulkiness) in ring B determine the potency of phenyl carbamates. (C) 2013 Elsevier Masson SAS. All rights reserved.