5-[(2-chlorophenyl)methylene]amino-1,3,4-thiadiazole-2-thiol | 256444-88-9

• 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-[(2-chlorophenyl)methylene]amino-1,3,4-thiadiazole-2-thiol
• 英文别名: 2-(2-chlorobenzylideneamino)-5-mercapto-1,3,4-thiadiazole；5-[(2-Chloro-benzylidene)-amino]-3h-[1,3,4]-thiadiazole-2-thione；5-[(2-chlorophenyl)methylideneamino]-3H-1,3,4-thiadiazole-2-thione
• CAS: 256444-88-9
• 化学式: C₉H₆ClN₃S₂
• 分子量: 255.752
• InChiKey: PDQQYRUYTIPAOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  3

反应信息

• 作为反应物：
  描述：

  5-[(2-chlorophenyl)methylene]amino-1,3,4-thiadiazole-2-thiol 、 氯化苄 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以76%的产率得到5-(benzylthio)-N-[(2-chlorophenyl)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：

  2-氯苯甲醛 、 2-氨基-5-巯基-1,3,4-噻二唑 以 乙醇 为溶剂， 以55%的产率得到5-[(2-chlorophenyl)methylene]amino-1,3,4-thiadiazole-2-thiol
  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：

文献信息

• 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).
• Morphological changes of some pathogenic microbial strains induced by novel thiadiazole derivatives
  作者：M. G. El-Gazzar、N. H. Zaher、S. Y. El-Tablawy

  DOI：10.1007/s00044-013-0779-x

  日期：2014.4

  In the quest for potent antimicrobial agents, some new 1,3,4-thiadiazole derivatives (2-11) were synthesized from the starting compound (1) 5-amino-1,3,4-thiadiazole-2(3H)-thione, with an aim to evaluate their antimicrobial effect on different pathogenic organisms isolated from microbial-infected cancer patients who had not yet received their radiation dose, compared to reference antibiotics. The titled compounds 5, 6, 10, and 11 were found to possess comparable or more potent activity than the reference compounds amikacin and sulperazone. Compound 5 was the most distinctive derivative identified in the present study because of its remarkable antibacterial activity exhibited against the Gram +ve strains, it has been scanned under electron microscope to determine the morphological changes that has taken place in the bacterial cells of Bacillus cereus and non-irradiated and irradiated Staphylococcus aureus. MIC of compound 5 and/or gamma irradiation affected the morphology of the tested strains causing; membrane damage, deformity on the surface of some cells, disappearance of the septum, elongation of some cells, and shortening of others. It may be hoped that the present study will encourage efforts toward the development of novel antibacterial agents that could be better in terms of efficacy and safety.
• 7-(4-((5-(2-chlorobenzylideneamino)-2-thioxo-1,3,4-thiadiazol-3(2H)-yl)methyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid as an anti-inflammatory compound
  申请人：KING FAISAL UNIVERISTY

  公开号：US11958848B1

  公开（公告）日：2024-04-16

  A 7-(4-((5-(2-chlorobenzylideneamino)-2-thioxo-1,3,4-thiadiazol-3(2H)-yl)methyl)piperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid compound, its synthesis, and its use as an anticancer and/or anti-inflammatory agent.