5-[3-(3-Trifluoromethyl-phenyl)-thioureido]-1H-pyrazole-4-carboxylic acid ethyl ester | 958386-41-9

• 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: 5-[3-(3-Trifluoromethyl-phenyl)-thioureido]-1H-pyrazole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 5-[[3-(trifluoromethyl)phenyl]carbamothioylamino]-1H-pyrazole-4-carboxylate
• CAS: 958386-41-9
• 化学式: C₁₄H₁₃F₃N₄O₂S
• 分子量: 358.344
• InChiKey: HIPGYDLEVSWAOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-[3-(3-Trifluoromethyl-phenyl)-thioureido]-1H-pyrazole-4-carboxylic acid ethyl ester 在 硫酸 作用下， 反应 96.0h， 以80%的产率得到6-(3-Trifluoromethyl-phenylamino)-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 、 阿尔法,阿尔法,阿尔法位-三氟-间-甲苯异硫氰 以 甲苯 为溶剂， 反应 6.0h， 以75%的产率得到5-[3-(3-Trifluoromethyl-phenyl)-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

文献信息

• Synthetic Pyrazole Derivatives as Growth Inhibitors of Some Phytopathogenic Fungi
  作者：Chiara B. Vicentini、Carlo Romagnoli、Elisa Andreotti、Donatella Mares

  DOI：10.1021/jf072077d

  日期：2007.12.1

  The present study was carried out to investigate the antifungal activity of pyrazole/isoxazole-3-carboxamido-4-carboxylic acids, 4-oxo-5-substituted pyrazolo[3,4-d]pyrimidine-6-thiones, and N-alkyl/aryl-N-(4-carbethoxy-3-pyrazolyl)thioureas against Pythium ultimum, Botrytis cinerea, and Magnaporthe grisea. The results on growth inhibition showed differences in the sensitivity of the three fungi to the tested substances, and in general P. ultimum was shown to be the most sensitive, On all phytopathogens the best results within the pyrazole/isoxazolecarboxamide series are given by the compounds with the carboxamide and carboxylic groups in positions 3 and 4; the presence of these groups seems to be critical for biological activity in this series of compounds. Among the pyrazolopyrimidines the derivative supplied with the benzylic group was the most active on the three fungi and in particular against P. ultimum. Several compounds belonging to the thiourea series are able to inhibit selectively M. grisea at 50 and 10 mu g mL(-1), doses at which the reference commercial compound tricyclazole had low or no effect.
• Pyrazole Derivatives as Photosynthetic Electron Transport Inhibitors:  New Leads and Structure−Activity Relationship
  作者：Chiara B. Vicentini、Salvatore Guccione、Laura Giurato、Rebecca Ciaccio、Donatella Mares、Giuseppe Forlani

  DOI：10.1021/jf0500029

  日期：2005.5.1

  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.