Synthesis and antimicrobial study of novel heterocyclic compounds from hydroxybenzophenones.
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.
Khanum
Shaukath A
SA
Department of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570005, India.
Shashikanth
Sheena
S
Umesha
S
S
Kavitha
R
R
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000494:pharmacology; D001577:Benzophenones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010069:Oxadiazoles / Q000138:chemical synthesis / Q000737:chemistry; D013829:Thiadiazines / Q000138:chemical synthesis / Q000737:chemistry
D000890:Anti-Infective Agents; D000935:Antifungal Agents; D001577:Benzophenones; D006571:Heterocyclic Compounds; D010069:Oxadiazoles; D013829:Thiadiazines; C047723:benzophenone