Synthesis, spectral analysis and pharmacological study of N’-substituted-2-(5-((2,4-dimethylphenoxy)methyl)-1,3,4-oxadiazol-2-ylthio)acetohydrazides

• Published in: Brazilian Journal of Pharmaceutical Sciences
• Main Author: Rasool S.; Aziz-ur-Rehman; Abbasi M.A.; Siddiqui S.Z.; Shah S.A.A.
• Format: Article
• Language: English
• Published: Faculdade de Ciencias Farmaceuticas (Biblioteca) 2016
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85006043172&doi=10.1590%2fs1984-82502016000300013&partnerID=40&md5=601a74d0191422325549fcfb7892de56

A series of molecules bearing multiple functional groups were synthesized to study their antibiotic effect against Gram-positive and Gram-negative bacteria and lipoxygenase activity as well. 2,4-Dimethylcarbolic acid (1) was refluxed with ethyl 2-bromoacetate to synthesize ethyl 2-(2,4-dimethylphenoxy)acetate (2). Compound 2 was converted to the corresponding hydrazide 3, again on refluxing with hydrazine. The compound 5-((2,4-dimethylphenoxy)methyl)-1,3,4-oxadiazol-2-thiol (4) was synthesized by the reaction of 3 and CS2 in the presence of KOH. Compound 4 was further converted to the corresponding ester 5 and then 2-(5-((2,4-dimethylphenoxy)methyl)-1,3,4-oxadiazol-2-ylthio)acetohydrazide (6). The final molecules N’-substituted-2-(5-((2,4-dimethylphenoxy)methyl)-1,3,4-oxadiazol-2-ylthio)acetohydrazide, 8a-m, bearing ether, 1,3,4-oxadiazole, thioether, hydrazone and azomethine functional groups were synthesized by stirring the aryl carboxaldehydes 7a-m with 6 in methanol at room temperature. The depicted structures of all synthesized molecules were corroborated by IR, 1H-NMR and EIMS spectral data analysis. 8m and 8i showed substantial antibacterial activity and lipoxygenase inhibitory activity, respectively. © 2016, Faculdade de Ciencias Farmaceuticas (Biblioteca). All rights reserved.