5-[(4-fluorophenyl)methylene]amino-1,3,4-thiadiazole-2-thiol

• 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-[(4-fluorophenyl)methylene]amino-1,3,4-thiadiazole-2-thiol
• 英文别名: 5-((4-fluorobenzylidene)amino)-1,3,4-thiadiazole-2-thiol；2-(4-flurobenzylideneamino)-5-mercapto-1,3,4-thiadiazole；5-[(E)-(4-fluorophenyl)methylideneamino]-3H-1,3,4-thiadiazole-2-thione
• 化学式: C₉H₆FN₃S₂
• 分子量: 239.297
• InChiKey: LRCDWSIEBBXSHM-VZUCSPMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[(4-fluorophenyl)methylene]amino-1,3,4-thiadiazole-2-thiol 、 氯化苄 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以71%的产率得到5-(benzylthio)-N-[(4-fluorophenyl)methylene]amino-1,3,4-thiadiazol-2-amine
  参考文献：
  名称：

  Ahmed, Bahar; Yusuf, Md., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 2, p. 241 - 246

  摘要：

  DOI：
• 作为产物：
  描述：

  对氟苯甲醛 、 2-氨基-5-巯基-1,3,4-噻二唑 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到5-[(4-fluorophenyl)methylene]amino-1,3,4-thiadiazole-2-thiol
  参考文献：
  名称：

  Antimicrobial and antitubercular evaluation of some new 5-amino-1,3,4-thiadiazole-2-thiol derived Schiff bases

  摘要：

  为了研究基于 1,3,4-噻二唑的分子对细菌、真菌和结核菌的影响，我们将多种羰基化合物与 5-氨基-1,3,4-噻二唑-2-硫醇反应，合成了一系列希夫碱（2a-2m）。这些化合物的分子结构是通过光谱方法和元素分析得到的。所有这些化合物的抗菌、抗真菌和抗结核活性均采用标准的生物学方法进行了评估。被退电子的氟和硝基取代的化合物 2m 和 2l 对金黄色葡萄球菌、黑曲霉和热带念珠菌具有极佳的抑制活性，其 MIC 值为 8 µg/mL，而含有释放电子的二甲基氨基的 2i 则对普通变形杆菌具有很强的活性。此外，2m 以及 2j、2k 和 2l 也显示出比标准吡嗪酰胺更强的抗霉菌活性。这些化合物的活性数据为开发新的抗菌和抗结核药物铺平了道路。

  DOI：

  10.33224/rrch.2020.65.9.01

文献信息

• Self-assembly of organooxotin(IV) clusters with Schiff-base-containing-triazole from hydrolysis or solvothermal synthesis: Crystal structures, hydrogen bonds, C–H⋯π stacking and S⋯S interaction
  作者：Chunlin Ma、Junshan Sun、Rufen Zhang、Daqi Wang

  DOI：10.1016/j.jorganchem.2007.04.039

  日期：2007.9

  All the complexes were characterized by elemental analysis, IR, 1H, 13C and 119Sn spectra analyses. Except for complexes 4 and 6, the other complexes are also characterized by X-ray crystallography diffraction analyses. Complexes 1–3 and 5 show similar structures containing a Sn4O4 ladder-shaped skeleton in which the N atom from a corresponding thione-form deprotonated Schiff base coordinated to the

  已经很容易通过水解或溶剂热合成途径合成了八种新的含席夫碱-三唑配体外围的基于有机锡氧烷的多氧化还原组件。二有机二氯化锡与含席夫碱的三唑配体的反应提供以下类型：[（Me 2 Sn）2 O 2（Ln）] 2（n  = 1，对于1）[（Me 2 Sn）2 O（RO）（Ln）] 2（R = Et，n  = 2，for 2 ; R = Me，n  = 3，for 3），[（n -Bu 2 Sn）2 O 2（Ln）] 2（n  = 1，代表4；n  = 2，代表5；n  = 3，代表6）和[（Me 2 Sn）2 Ln 2 O] 2  ·L（n  = 2; L = H 2 O代表7，L = CH 3 OH为8）。通过元素分析，IR，1 H，13 C和119 Sn光谱分析对所有配合物进行表征。配合物4和6除外，其他配合物也通过X射线晶体学衍射分析来表征。配合物1 - 3和5示出具有Sn类似结构4 ø 4梯
• An Interactive Human Carbonic Anhydrase-II (hCA-II) Receptor - Pharmacophore Molecular Model & Anti-Convulsant Activity of the Designed and Synthesized 5-Amino-1,3,4-Thiadiazole-2-Thiol Conjugated Imine Derivatives
  作者：Mohammad Yusuf、Riaz A. Khan、Maria Khan、Bahar Ahmed

  DOI：10.1111/cbdd.12113

  日期：2013.5

  New imines, derived from aromatic aldehyde, chalcones and 5‐amino‐1,3,4‐thiadiazole‐2‐thiol exhibited promising anti‐convulsant activity which is explained through chemo‐biological interactions at receptor site producing the inhibition of human Carbonic Anhydrase‐II enzyme (hCA‐II) through the proposed pharmacophore model at molecular levels as basis for pharmacological activity. The compounds 5‐1‐(4‐Chlorophenyl)‐3‐[4‐(methoxy‐phenyl)‐prop‐2‐en‐1‐ylidene]amino}‐1,3,4‐thiadiazole‐2‐thiol (2b), 5‐[1‐(4‐chloro‐phenyl)]‐3‐[4‐(dimethyl‐amino‐phenyl)‐prop‐2‐en‐1‐ylidene]amino}‐1,3,4‐thiadiazole‐2‐thiol (2c) and 5‐[1‐(4‐chloro‐phenyl)]‐3‐[(4‐amino‐phenyl)‐prop‐2‐en‐1‐ylidene]amino}‐1,3,4‐thiadiazole‐2‐thiol (2f) showed 100% activity in comparison with standard Acetazolamide, a known anti‐convulsant drug. The compounds 2c, 2f also passed the Rotarod and Ethanol Potentiation tests which further confirmed them to be safe in motor coordination activity and safe from generating neurological toxicity.
• SYNTHESIS OF SOME NOVEL AND BIOLOGICALLY ACTIVE SCHIFF BASES BEARING A 1,3,4-THIADIAZOLE MOIETY UNDER ACIDIC AND PTC CONDITIONS
  作者：A MOBINIKHALEDI、M JABBARPOUR、A HAMTA

  DOI：10.4067/s0717-97072011000300020

  日期：——

  The synthesis of some new Schiff bases bearing a 1,3,4-thiadiazole moiety, 3a-1, by reaction of 2-amino-5-mercapto-1,3,4-thiadiazole with aromatic aldehydes under acidic and phase transfer catalyst (PTC) conditions was studied. The structure of all the Schiff bases was characterized using FT-IR and NMR spectroscopy, and elemental analyses. The antibacterial activity of these compounds was investigated against Staphylococcus aureus (RTCC, 1885), and Escherichia coli (ATCC, 35922).
• Ahmed, Bahar; Yusuf, Md., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 2, p. 241 - 246
  作者：Ahmed, Bahar、Yusuf, Md.

  DOI：——

  日期：——
• Antimicrobial and antitubercular evaluation of some new 5-amino-1,3,4-thiadiazole-2-thiol derived Schiff bases
  作者：Kasetti Ashok BABU、Indrajeet SINGHVI、Nagasuri RAVINDRA、Afzal Basha SHAIK

  DOI：10.33224/rrch.2020.65.9.01

  日期：——

  In an effort to study the effect of 1,3,4-thidiazole based molecules on bacteria, fungal and tuberculosis species, we synthesized a series of Schiff bases (2a-2m) by reacting a variety of carbonyl compounds with 5-amino-1,3,4- thiadiazole-2-thiol. Molecular structure of these compounds was retrieved by spectral methods and elemental analysis. All these compounds were evaluated for their antibacterial, antifungal and antitubercular activities employing standard biological protocols. The compounds 2m and 2l substituted with the electron withdrawing fluorine and nitro groups showed excellent inhibitory activity against Staphylococcus aureus, Aspergillus niger and Candida tropicalis with an MIC of 8 µg/mL whereas 2i containing the electron releasing dimethylamino group showed potent activity against Proteus vulgaris. Additionally, 2m along with 2j, 2k and 2l also exhibited superior antimycobacterial activity than the standard pyrazinamide. The activity data for these compounds pave the way for the development of new antimicrobial and antitubercular drugs.

  为了研究基于 1,3,4-噻二唑的分子对细菌、真菌和结核菌的影响，我们将多种羰基化合物与 5-氨基-1,3,4-噻二唑-2-硫醇反应，合成了一系列希夫碱（2a-2m）。这些化合物的分子结构是通过光谱方法和元素分析得到的。所有这些化合物的抗菌、抗真菌和抗结核活性均采用标准的生物学方法进行了评估。被退电子的氟和硝基取代的化合物 2m 和 2l 对金黄色葡萄球菌、黑曲霉和热带念珠菌具有极佳的抑制活性，其 MIC 值为 8 µg/mL，而含有释放电子的二甲基氨基的 2i 则对普通变形杆菌具有很强的活性。此外，2m 以及 2j、2k 和 2l 也显示出比标准吡嗪酰胺更强的抗霉菌活性。这些化合物的活性数据为开发新的抗菌和抗结核药物铺平了道路。