Karegoudar Prakash, Prasad D Jagdeesh, Ashok Mithun, Mahalinga Manjathuru, Poojary Boja, Holla Bantwal Shivarama
Sequent Scientific Limited, 120 A & B, Industrial Area, Bikampady, New Mangalore, Karnataka, India.
Eur J Med Chem. 2008 Apr;43(4):808-15. doi: 10.1016/j.ejmech.2007.06.026. Epub 2007 Jul 17.
The reaction of 2,3,5-trichlorobenzoic acid hydrazide with carbon disulfide and potassium hydroxide followed by treatment with hydrazine hydrate afforded 3-(2,3,5-trichlorophenyl)-4-amino-1,2,4-triazole-5-thione (6). Alternatively, this triazole was also synthesized by fusing 2,3,5-trichlorobenzoic acid with thiocarbohydrazide. Condensation of (6) with various aromatic carboxylic acids in the presence of phosphorous oxychloride or with phenacyl bromides afforded two series of fused heterocycles namely 6-(substituted aryl)-3-(2,3,5-trichlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadizoles (7) and 6-(substituted aryl)-3-(2,3,5-trichlorophenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines (8), respectively. The structures of these newly synthesized compounds are characterised by elemental analysis, IR, (1)H NMR and mass spectroscopic studies. All the synthesized compounds were screened for their antimicrobial and anti-inflammatory activities. Some of the compounds exhibited promising antimicrobial and anti-inflammatory activities.
2,3,5-三氯苯甲酰肼与二硫化碳和氢氧化钾反应，随后用水合肼处理，得到3-(2,3,5-三氯苯基)-4-氨基-1,2,4-三唑-5-硫酮(6)。另外，该三唑也可通过将2,3,5-三氯苯甲酸与硫代碳酰肼熔融来合成。(6)与各种芳香族羧酸在三氯氧磷存在下缩合，或与苯甲酰溴缩合，分别得到两个系列的稠合杂环，即6-(取代芳基)-3-(2,3,5-三氯苯基)-[1,2,4]三唑并[3,4-b][1,3,4]噻二唑(7)和6-(取代芳基)-3-(2,3,5-三氯苯基)-7H-[1,2,4]三唑并[3,4-b][1,3,4]噻二嗪(8)。这些新合成化合物的结构通过元素分析、红外光谱、核磁共振氢谱和质谱研究进行了表征。对所有合成化合物进行了抗菌和抗炎活性筛选。一些化合物表现出有前景的抗菌和抗炎活性。
