5-[2-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)ethyl]-3H-1,3,4-thiadiazole-2-thione | 21528-04-1

• 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-[2-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)ethyl]-3H-1,3,4-thiadiazole-2-thione
• CAS: 21528-04-1
• 化学式: C₆H₆N₄S₄
• 分子量: 262.404
• InChiKey: XBWXGOHXKNWLBI-UHFFFAOYSA-N

物化性质

• 熔点：
  298 °C (decomp)
• 沸点：
  395.8±52.0 °C(Predicted)
• 密度：
  1.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  164
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O,O-二乙基硫代磷酰氯 、 5-[2-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)ethyl]-3H-1,3,4-thiadiazole-2-thione 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 70.0h， 以68%的产率得到[5-[2-(5-Diethoxyphosphinothioylsulfanyl-1,3,4-thiadiazol-2-yl)ethyl]-1,3,4-thiadiazol-2-yl]sulfanyl-diethoxy-sulfanylidene-lambda5-phosphane
  参考文献：
  名称：

  Efficacy of Organophosphorus Derivatives against Fungal Pathogens of Sugarcane

  摘要：

  Several novel oraganophosphorus derivatives have been prepared by the reactions of O,O-diethyl chlorophosphate/thiophosphate with three important series of heterocyclic compounds, viz., bis(mercaptotriazoles), bis(mercaptooxadiazoles), and bis(mercaptothiadiazoles). The derivatives have been characterized on the basis of analyses and spectral (IR, (1)H NMR, and (31)P NMR) data. The fungicidal activity of these derivatives against Colletotrichum falcatum, Fusarium oxysporum, and Curvularia pallescens have been evaluated. The screening results have been correlated with the structural features of the tested compounds. The greater potency has been observed with dithiophosphates compared to phosphates, with organophosphorus derivatives containing bis(mercaptotriazole) rings compared to other heterocyclic rings, and with long spacers between the rings.

  DOI：

  10.1021/jf970544t
• 作为产物：
  描述：

  在 硫酸 作用下， 生成 5-[2-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)ethyl]-3H-1,3,4-thiadiazole-2-thione
  参考文献：
  名称：

  Efficacy of Organophosphorus Derivatives against Fungal Pathogens of Sugarcane

  摘要：

  Several novel oraganophosphorus derivatives have been prepared by the reactions of O,O-diethyl chlorophosphate/thiophosphate with three important series of heterocyclic compounds, viz., bis(mercaptotriazoles), bis(mercaptooxadiazoles), and bis(mercaptothiadiazoles). The derivatives have been characterized on the basis of analyses and spectral (IR, (1)H NMR, and (31)P NMR) data. The fungicidal activity of these derivatives against Colletotrichum falcatum, Fusarium oxysporum, and Curvularia pallescens have been evaluated. The screening results have been correlated with the structural features of the tested compounds. The greater potency has been observed with dithiophosphates compared to phosphates, with organophosphorus derivatives containing bis(mercaptotriazole) rings compared to other heterocyclic rings, and with long spacers between the rings.

  DOI：

  10.1021/jf970544t

文献信息

• Kato; Ohta, Nippon Kagaku Zasshi, 1957, vol. 78, p. 1588,1590
  作者：Kato、Ohta

  DOI：——

  日期：——
• Azolylthioacetamides as a potent scaffold for the development of metallo-β-lactamase inhibitors
  作者：Yang Xiang、Ya-Nan Chang、Ying Ge、Joon S. Kang、Yi-Lin Zhang、Xiao-Long Liu、Peter Oelschlaeger、Ke-Wu Yang

  DOI：10.1016/j.bmcl.2017.10.038

  日期：2017.12

  In an effort to develop new inhibitors of metallo-beta-lactamases (MbLs), twenty-eight azolylthioacetamides were synthesized and assayed against MbLs. The obtained benzimidazolyl and benzioxazolyl substituted 1-19 specifically inhibited the enzyme ImiS, and 10 was found to be the most potent inhibitor of ImiS with an IC50 value of 15 nM. The nitrobenzimidazolyl substituted 20-28 specifically inhibited NDM-1, with 27 being the most potent inhibitor with an IC50 value of 170 nM. Further studies with 10, 11, and 27 revealed a mixed inhibition mode with competitive and uncompetitive inhibition constants in a similar range as the IC50 values. These inhibitors resulted in a 2-4-fold decrease in imipenem MIC values using E. coli cells producing ImiS or NDM-1. While the source of uncompetitive (possibly allosteric) inhibition remains unclear, docking studies indicate that 10 and 11 may interact orthosterically with Zn2 in the active site of CphA, while 27 could bridge the two Zn(II) ions in the active site of NDM-1 via its nitro group. (C) 2017 Elsevier Ltd. All rights reserved.
• Efficacy of Organophosphorus Derivatives against Fungal Pathogens of Sugarcane
  作者：A. K. Jaiswal、G. P. Rao、O. P. Pandey、S. K. Sengupta

  DOI：10.1021/jf970544t

  日期：1998.4.1

  Several novel oraganophosphorus derivatives have been prepared by the reactions of O,O-diethyl chlorophosphate/thiophosphate with three important series of heterocyclic compounds, viz., bis(mercaptotriazoles), bis(mercaptooxadiazoles), and bis(mercaptothiadiazoles). The derivatives have been characterized on the basis of analyses and spectral (IR, (1)H NMR, and (31)P NMR) data. The fungicidal activity of these derivatives against Colletotrichum falcatum, Fusarium oxysporum, and Curvularia pallescens have been evaluated. The screening results have been correlated with the structural features of the tested compounds. The greater potency has been observed with dithiophosphates compared to phosphates, with organophosphorus derivatives containing bis(mercaptotriazole) rings compared to other heterocyclic rings, and with long spacers between the rings.