5-(3-Chlorophenyl)-6-sulfanyl-2H,4H,5H-pyrazolo[3,4-D]pyrimidin-4-one | 958386-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 5-(3-Chlorophenyl)-6-sulfanyl-2H,4H,5H-pyrazolo[3,4-D]pyrimidin-4-one
• 英文别名: 5-(3-chlorophenyl)-6-sulfanylidene-1,7-dihydropyrazolo[3,4-d]pyrimidin-4-one
• CAS: 958386-16-8
• 化学式: C₁₁H₇ClN₄OS
• mdl: MFCD04063370
• 分子量: 278.722
• InChiKey: KOTVXEYITOQIPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  88.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-[3-(3-Chloro-phenyl)-thioureido]-1H-pyrazole-4-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 水 为溶剂， 以65%的产率得到5-(3-Chlorophenyl)-6-sulfanyl-2H,4H,5H-pyrazolo[3,4-D]pyrimidin-4-one
  参考文献：
  名称：

  Synthetic Pyrazole Derivatives as Growth Inhibitors of Some Phytopathogenic Fungi

  摘要：

  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.

  DOI：

  10.1021/jf072077d

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.