5-(3-Cyclohexyl-thioureido)-1H-pyrazole-4-carboxylic acid ethyl ester | 958386-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3-Cyclohexyl-thioureido)-1H-pyrazole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 5-(cyclohexylcarbamothioylamino)-1H-pyrazole-4-carboxylate
• CAS: 958386-65-7
• 化学式: C₁₃H₂₀N₄O₂S
• 分子量: 296.393
• InChiKey: FUESAAVMFILNJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-Cyclohexyl-thioureido)-1H-pyrazole-4-carboxylic acid ethyl ester 在 硫酸 作用下， 反应 96.0h， 以84%的产率得到6-(cyclohexylamino)-1H-pyrazolo[3,4-d][1,3]thiazin-4-one
  参考文献：
  名称：

  Pyrazole Derivatives as Photosynthetic Electron Transport Inhibitors:  New Leads and Structure−Activity Relationship

  摘要：

  Four series of new pyrazoles, namely, 5 4-carboxypyrazolo-3-tert-butylcarboxamide and 6 4-carboxypyrazolo-3-cyclopropylcarboxamide derivatives and 10 pyrazolo[3,4-d][1,3]thiazine-4-one and 9 pyrazolo[3,4-d][1,3]thiazine-4-thione derivatives, were synthesized and screened as potential inhibitors of photosynthetic electron transport. The structures were confirmed by H-1 NMR, elemental, and IR analyses. Their biological activity was evaluated in vitro as the ability to interfere with the light-driven reduction of ferricyanide by isolated spinach chloroplasts. Only a few compounds exhibited excellent inhibitory properties in the micromolar range, comparable to those of commercial herbicides sharing the same target, such as diuron, lenacil, and hexazinone. Nevertheless, most of the remaining molecules exerted a remarkable inhibition in the millimolar range. Combined with previous results on 6 pyrazolo[1,5-a][1,3,5]triazine-2,4-dione and 4 pyrazolo[1,5-c][1,3,5]thiadiazine-2-one derivatives, these data allowed a comprehensive analysis of structure-activity relationship. Molecular modeling studies were undertaken to rationalize the structural determinants of activity in terms of shape, size, and molecular fields. Results suggested that the inhibitory potential of these compounds is associated mainly with their electrostatic properties.

  DOI：

  10.1021/jf0500029
• 作为产物：
  描述：

  3-氨基-4-乙氧羰基吡唑 、 环己基异硫氰酸脂 以 甲苯 为溶剂， 反应 6.0h， 以8%的产率得到5-(3-Cyclohexyl-thioureido)-1H-pyrazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Pyrazole Derivatives as Photosynthetic Electron Transport Inhibitors:  New Leads and Structure−Activity Relationship

  摘要：

  Four series of new pyrazoles, namely, 5 4-carboxypyrazolo-3-tert-butylcarboxamide and 6 4-carboxypyrazolo-3-cyclopropylcarboxamide derivatives and 10 pyrazolo[3,4-d][1,3]thiazine-4-one and 9 pyrazolo[3,4-d][1,3]thiazine-4-thione derivatives, were synthesized and screened as potential inhibitors of photosynthetic electron transport. The structures were confirmed by H-1 NMR, elemental, and IR analyses. Their biological activity was evaluated in vitro as the ability to interfere with the light-driven reduction of ferricyanide by isolated spinach chloroplasts. Only a few compounds exhibited excellent inhibitory properties in the micromolar range, comparable to those of commercial herbicides sharing the same target, such as diuron, lenacil, and hexazinone. Nevertheless, most of the remaining molecules exerted a remarkable inhibition in the millimolar range. Combined with previous results on 6 pyrazolo[1,5-a][1,3,5]triazine-2,4-dione and 4 pyrazolo[1,5-c][1,3,5]thiadiazine-2-one derivatives, these data allowed a comprehensive analysis of structure-activity relationship. Molecular modeling studies were undertaken to rationalize the structural determinants of activity in terms of shape, size, and molecular fields. Results suggested that the inhibitory potential of these compounds is associated mainly with their electrostatic properties.

  DOI：

  10.1021/jf0500029