Khanum Shaukath A, Shashikanth Sheena, Umesha S, Kavitha R
Department of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570005, India.
Eur J Med Chem. 2005 Nov;40(11):1156-62. doi: 10.1016/j.ejmech.2005.04.005. Epub 2005 Jun 1.
The triazolothiadiazine analogues 6a-e were obtained via a multistep synthesis sequences beginning with the hydroxybenzophenones 1a-e. Hydroxybenzophenones on reaction with ethyl chloroacetate affords ethyl (2-aroylaryloxy)acetates 2a-e which on treatment with hydrazine hydrate yields 2-(2-aroylaryloxy)acetohydrazides 3a-e. Intramolecular cyclization of 3a-e with carbon disulfide affords 5-(2-aroylaryloxy)methyl-1,3,4-oxadiazole-2-(3H)thiones 4a-e, which on treatment with hydrazine hydrate yields 4-amino-5-(2-aroyl aryloxy)methyl-1,2,4-triazole-3-(2H)thiones 5a-e. Condensation of 5a-e with alpha-halocarbonyl compound results in 3-(2-aroylaryloxy)methyl-6-phenyl-1,2,4-triazolo[3,4-b][1,3,4] thiadiazine 6a-e analogues. The compounds 4a-e, 5a-e and 6a-e were tested against variety of fungal and bacterial strains in comparison to fluconazole and chloramphenicol, respectively.
三唑并噻二嗪类似物6a - e是通过以羟基二苯甲酮1a - e为起始原料的多步合成序列得到的。羟基二苯甲酮与氯乙酸乙酯反应得到(2 - 芳酰基芳氧基)乙酸乙酯2a - e，2a - e与水合肼反应生成2 - (2 - 芳酰基芳氧基)乙酰肼3a - e。3a - e与二硫化碳进行分子内环化反应得到5 - (2 - 芳酰基芳氧基)甲基 - 1,3,4 - 恶二唑 - 2 - (3H)硫酮4a - e，4a - e与水合肼反应生成4 - 氨基 - 5 - (2 - 芳酰基芳氧基)甲基 - 1,2,4 - 三唑 - 3 - (2H)硫酮5a - e。5a - e与α - 卤代羰基化合物缩合得到3 - (2 - 芳酰基芳氧基)甲基 - 6 - 苯基 - 1,2,4 - 三唑并[3,4 - b][1,3,4]噻二嗪6a - e类似物。分别与氟康唑和氯霉素相比，对化合物4a - e、5a - e和6a - e针对多种真菌和细菌菌株进行了测试。
