Abstract
Acetic acid hydrazide containing 5-methyl-2-benzoxazolinone (4) was synthesized by the condensation of 2-(5-methyl-2-benzoxazolinone-3-yl)acetate with hydrazine hydrate. Thiosemicarbazide derivatives (5a-5d) were afforded by the reaction of corresponding compound 4 with substituted isothiocyanates. The cyclization of compounds 5a-5d in the presence of triethylamine resulted in the formation of compounds 6a-6d containing 1,2,4-triazole ring. On the other hand, the treatment of compounds 5a-5d with orthophosphoric acid caused the conversion of side chain of compounds 5a-5d into 1,3,4-thiadiazole ring: thus, compounds 7a-7c were obtained. The treatment of compound 4 with aromatic aldehydes resulted in the formation of arylidene hydrazides as cis-trans conformers (8a-8e). The structures of the compounds were elucidated by spectral and elemental analysis. While most compounds were exhibiting high activity in the analgesic-anti-inflammatory field, most of them were found to be inactive against bacteria and fungi.
MeSH terms
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Analgesics / chemical synthesis
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Analgesics / chemistry
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Analgesics / pharmacology
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Animals
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Anti-Bacterial Agents / chemical synthesis
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Anti-Bacterial Agents / chemistry*
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Anti-Bacterial Agents / pharmacology
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Anti-Inflammatory Agents / chemical synthesis
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Anti-Inflammatory Agents / chemistry
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Anti-Inflammatory Agents / pharmacology
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Anti-Inflammatory Agents / therapeutic use
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Benzoxazoles / chemistry*
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Crystallography, X-Ray
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Edema / drug therapy
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Edema / pathology
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Hindlimb / drug effects
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Hydrazones / chemical synthesis*
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Hydrazones / chemistry
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Hydrazones / pharmacology*
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Hydrazones / therapeutic use
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Methylation
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Mice
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Microbial Viability / drug effects
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Models, Molecular
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Molecular Structure
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Semicarbazides / chemical synthesis*
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Semicarbazides / chemistry
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Semicarbazides / pharmacology
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Semicarbazides / therapeutic use
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Structure-Activity Relationship
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Thiadiazoles / chemical synthesis*
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Thiadiazoles / chemistry
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Thiadiazoles / pharmacology
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Thiadiazoles / therapeutic use
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Triazoles / chemical synthesis*
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Triazoles / chemistry
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Triazoles / pharmacology
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Triazoles / therapeutic use
Substances
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Analgesics
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Anti-Bacterial Agents
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Anti-Inflammatory Agents
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Benzoxazoles
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Hydrazones
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Semicarbazides
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Thiadiazoles
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Triazoles
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1,3,4-thiadiazole
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mercaptotriazole
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benzoxazolone
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thiosemicarbazide