N-(4,5-dihydro-1-phenylpyrazol-3-yl)-2,4-dihydroxythiobenzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(4,5-dihydro-1-phenylpyrazol-3-yl)-2,4-dihydroxythiobenzamide
• 英文别名: 2,4-dihydroxy-N-(1-phenylpyrazolidin-3-ylidene)benzenecarbothioamide
• 化学式: C₁₆H₁₅N₃O₂S
• 分子量: 313.38
• InChiKey: AUAWLLHZYMJVSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  100
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氨基-4,5-二氢-1-苯基吡唑 、 bis-(2,4-dihydroxythiobenzoyl)sulfinyl 以 甲醇 为溶剂， 反应 3.0h， 生成 N-(4,5-dihydro-1-phenylpyrazol-3-yl)-2,4-dihydroxythiobenzamide
  参考文献：
  名称：

  Synthesis and antimycotic activity of N-azolyl-2,4-dihydroxythiobenzamides

  摘要：

  N-pyrazole and N-1,2,4-triazole derivatives of 2,4-dihydroxythiobenzamide prepared from sulfinyl-bis-(2,4-dihydroxythiobenzoyl) and commercially available azole amines were tested for their antimycotic activity. The chemical structure of compounds was confirmed by IR, H-1 NMR, MS and elemental analysis. The MIC values against the reference strain Candida albicans ATCC 10231, azole-resistant clinical isolates of Candida albicans and non-Candida albicans species were determined for their potential activity in vitro. The compounds exhibited comparable or higher activity than itraconazole and fluconazole tested under the same experimental conditions. Pyrazoline derivatives showed higher activity than other analogues. The strongest fungistatic activity for N-(2,3-dimethyl-1-phenyl-1,2-dihydro-5-oxo-5H-pyrazol-4-yl)-2,4-dihydroxythiobenzamide was found with MIC values significantly lower than those for the studied drugs. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00110-x

文献信息

• Synthesis and antimycotic activity of N-azolyl-2,4-dihydroxythiobenzamides
  作者：Joanna Matysiak、Andrzej Niewiadomy

  DOI：10.1016/s0968-0896(03)00110-x

  日期：2003.5

  N-pyrazole and N-1,2,4-triazole derivatives of 2,4-dihydroxythiobenzamide prepared from sulfinyl-bis-(2,4-dihydroxythiobenzoyl) and commercially available azole amines were tested for their antimycotic activity. The chemical structure of compounds was confirmed by IR, H-1 NMR, MS and elemental analysis. The MIC values against the reference strain Candida albicans ATCC 10231, azole-resistant clinical isolates of Candida albicans and non-Candida albicans species were determined for their potential activity in vitro. The compounds exhibited comparable or higher activity than itraconazole and fluconazole tested under the same experimental conditions. Pyrazoline derivatives showed higher activity than other analogues. The strongest fungistatic activity for N-(2,3-dimethyl-1-phenyl-1,2-dihydro-5-oxo-5H-pyrazol-4-yl)-2,4-dihydroxythiobenzamide was found with MIC values significantly lower than those for the studied drugs. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis and Fungistatic Activity of New Groups of 2,4-Dihydroxythiobenzoyl Derivatives against Phytopathogenic Fungi
  作者：Jan Legocki、Joanna Matysiak、Andrzej Niewiadomy、Małgorzata Kostecka

  DOI：10.1021/jf0206769

  日期：2003.1.1

  Twenty-six compounds, derivatives of amides, hydrazines, hydrazides, hydrazones, and semicarbazides, with a 2,4-dihydroxythiobenzoyl moiety, were synthesized from sulfinyl-bis(2,4-dihydroxythiobenzoyl). The compositions and chemical structures of these compounds were confirmed by IR, H-1 NMR, EI-MS, and elemental analysis. Antifungal properties of chemicals under in vitro conditions against five phytopathogenic fungi were estimated. In vivo studies against Erisiphe graminis were also carried out. The compounds N-substituted with an 2,4-dihydroxythiobenzamide group proved to be the most active. N-2-(1-Cinnamylbenzene ester)-2,4-dihydroxythiobenzamide, under in vitro conditions, showed activity at the level of 80-100% development of most pathogens at a concentration of 20 mug/mL and partially at a concentration of 200 mug/mL. For compounds with -HN-NH- or -NH-N= moiety, weak or no fungistatic properties were found at the concentrations studied.