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

• Main Authors: Abbasi, M.A (Author), Aziz-ur-Rehman (Author), Rasool, S. (Author), Shah, S.A.A (Author), Siddiqui, S.Z (Author)
• Format: Article
• Language: English
• Published: Faculdade de Ciencias Farmaceuticas (Biblioteca) 2016
• Subjects: 1,3,4 oxadiazole derivative; 2,4 dimethylcarbolic acid; 5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 thiol; acetic acid; Acetohydrazides/antibacterial activity/acetohydrazides/lipoxygenase/inhibition activity; Acetohydrazides/synthesis; antibacterial activity; Article; azomethine ylide; Bacillus subtilis; baicalein; controlled study; drug structure; drug synthesis; enzyme inhibition; Escherichia coli; ether; ethyl 2 (2,4 dimethylphenoxy)acetate; ethyl 2 bromoacetate; hydrazide; hydrazone derivative; infrared spectroscopy; lipoxygenase; mass spectrometry; methanol; minimum inhibitory concentration; n' (2 hydroxybenzylidene) 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide; n' (2 methylbenzylidene) 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide; n' (2 nitrobenzylidene) 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide; n' (3 hydroxybenzylidene) 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide; n' (3 methylbenzylidene) 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide; n' (3 nitrobenzylidene) 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide; n' (4 hydroxybenzylidene) 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide; n' (4 methoxybenzylidene) 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide; n' (4 methylbenzylidene) 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide; n' (4 nitrobenzylidene) 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide; n' [4 (diethylamino)benzylidene] 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide; n' [4 (dimethylamino)benzylidene] 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide; n' 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide derivative; n' benzylidene 2 [5 [(2,4 dimethylphenoxy)methyl] 1,3,4 oxadiazol 2 ylthio]acetohydrazide; nonhuman; phenol; proton nuclear magnetic resonance; Pseudomonas aeruginosa; room temperature; Salmonella enterica serovar Typhi; Staphylococcus aureus; thiol; unclassified drug
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 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.