(4H-[1,2,4]triazol-3-ylsulfanyl)-acetic acid hydrazide | 24127-94-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (4H-[1,2,4]triazol-3-ylsulfanyl)-acetic acid hydrazide
• 英文别名: 2-(1H-1,2,4-triazol-5-ylsulfanyl)acetohydrazide
• CAS: 24127-94-4
• 化学式: C₄H₇N₅OS
• 分子量: 173.198
• InChiKey: DWFDSKPYRBJWSD-UHFFFAOYSA-N

物化性质

• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4H-[1,2,4]triazol-3-ylsulfanyl)-acetic acid hydrazide 生成 (1H-[1,2,4]triazol-3-ylsulfanyl)-acetic acid N'-(4-chloro-phenylcarbamoyl)-hydrazide
  参考文献：
  名称：

  RUDNICKA W.; SAWLEWICZ J., ACTA POL. PHARM., 1978, 35, NO 2, 135-142

  摘要：

  DOI：
• 作为产物：
  描述：

  (4H-[1,2,4]Triazol-3-ylsulfanyl)-acetic acid ethyl ester 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 (4H-[1,2,4]triazol-3-ylsulfanyl)-acetic acid hydrazide
  参考文献：
  名称：

  Unique Azolyl Acylhydrazonyl Hybridization of Aloe Emodins to Access Potential Antibacterial Agents

  摘要：

  A type of unique azole‐hybridized acylhydrazonyl aloe emodins (AAEs) were developed as new antibacterial agents for combating bacterial infections. Some target AAEs showed strong antibacterial activities, especially, tetrazolylthioether AAE 27a exhibited broad antibacterial spectrum with 16—256 folds and 8—64 folds more active antibacterial efficacy than the reference drugs aloe emodin and norfloxacin, respectively. Tetrazolylthioether AAE 27a also gave low hemolysis and cytotoxicity, as well as favorable bioavailability. Preliminary mechanism explorations revealed that tetrazolylthioether AAE 27a could cause bacterial membrane depolarization and damage the cell membrane, resulting in nucleic acid leakage. Moreover, compound 27a could intercalate into DNA to impede its replication and form supramolecular 27a‐DNA gyrase complex to disturb the function of DNA gyrase. These findings would provide valuable insights for the further exploration of azolyl acylhydrazonyl aloe emodins as new potential antibacterial candidates.

  DOI：

  10.1002/cjoc.202400160

文献信息

• Synthesis and antimicrobial activity of N-[(α-methyl)benzylidene]-(3-substituted-1,2,4-triazol-5-yl-thio)acetohydrazides
  作者：Seyhan Ersan、Sultan Nacak、Rukiye Berkem

  DOI：10.1016/s0014-827x(98)00095-0

  日期：1998.12

  In this study 18 new hydrazones have been synthesized by reacting ortho- or para-substituted acetophenones with (3-substituted-1,2,4-triazol-5-yl-thio)acetohydrazide in ethanol. The prepared compounds were tested for antimicrobial activity. The prepared compounds exhibited only poor activity against Gram (+) and Gram (-) bacteria with the minimal inhibitory concentration (MIC) > or = 400 micrograms/ml. Moderate activity was observed against Candida species with MIC in the range 100-400 micrograms/ml.
• RUDNICKA W.; SAWLEWICZ J., ACTA POL. PHARM., 1978, 35, NO 2, 135-142
  作者：RUDNICKA W.、 SAWLEWICZ J.

  DOI：——

  日期：——
• Unique Azolyl Acylhydrazonyl Hybridization of Aloe Emodins to Access Potential Antibacterial Agents
  作者：Yi‐Xin Wang、Zhao Deng、Aisha Bibi、Bo Fang、Cheng‐He Zhou

  DOI：10.1002/cjoc.202400160

  日期：——

  A type of unique azole‐hybridized acylhydrazonyl aloe emodins (AAEs) were developed as new antibacterial agents for combating bacterial infections. Some target AAEs showed strong antibacterial activities, especially, tetrazolylthioether AAE 27a exhibited broad antibacterial spectrum with 16—256 folds and 8—64 folds more active antibacterial efficacy than the reference drugs aloe emodin and norfloxacin, respectively. Tetrazolylthioether AAE 27a also gave low hemolysis and cytotoxicity, as well as favorable bioavailability. Preliminary mechanism explorations revealed that tetrazolylthioether AAE 27a could cause bacterial membrane depolarization and damage the cell membrane, resulting in nucleic acid leakage. Moreover, compound 27a could intercalate into DNA to impede its replication and form supramolecular 27a‐DNA gyrase complex to disturb the function of DNA gyrase. These findings would provide valuable insights for the further exploration of azolyl acylhydrazonyl aloe emodins as new potential antibacterial candidates.