Synthesis and Antibacterial Activity of Some New 2,5‐Disubstituted‐1,3,4‐oxadiazole Derivatives

Abstract

,4-oxadiazole (5a-5i) were obtained in good yields via cyclisation of 1 and subjected to antibacterial activity test against pathogenic bacteria. The halogen containing mono-and di-substituted derivatives showed excellent antibacterial activity compared to other analogues.

Crystal structure of (E)-2-((2-(2,4-dinitrophenyl)hydrazono)methyl)-4-nitrophenol — triethylamine (2/1), C32H33N11O14

“…It is well-known that Schi base compounds have continued to enjoy extensive interests owing to their structural diversity and potential applications in pharmacology and catalysis [1,2]. The chelating salicylaldehyde derivatives ligands containing O and N donor atoms show broad biological activity, especially with one or more halogen atoms added in the aromatic ring (e.g.…”

A new and efficient method for the synthesis of 2-N-(aryl)-1,3,4-oxadiazole-2,5-diamine derivatives

“…The outcomes of these particular reagents, including Burgess-type [10,11] reagents and phosphonium salts, in inflexible byproduct materialization, conversely, have generally been limited to usage in solidphase synthetic strategies. Recently, the Boger group [12,13] reported an exciting method to synthesize 2-amino- [1,3,4]-oxadiazoles via the dehydrative cyclisation of a semicarbazide substrates mediated by tosyl chloride and a base at conventional room temperature [14,15]. We have been paying attention to this methodology due to the low price of reagents and mild reaction conditions.…”

“…We have been paying attention to this methodology due to the low price of reagents and mild reaction conditions. Typically, 2,5-diamino- [1,3,4]oxadiazole derivatives are prepared by cyclization of the corresponding acyclic hydrazine-1,2-dicarboxamide substrates, semicarbazides and thiosemicarbazides [16]. We have a current interest in the development of novel strategies to access functionalized oxadiazoles.…”

“…In specific, the improvement of an efficient and practical synthesis of 2,5-disubstituted-1,3,4-oxadiazoles is an active subject of current organic research. In the course of our research, we became interested in 1,3,4-oxadiazoles as they are rousing and versatile building blocks with a wide range of biological activities, including the following: antibacterial, antiviral, anti-inflammatory, antitubercular, antipyretic, anticancer, central nervous system depressant, antischistosomal, diuretic, analgesic, anticonvulsive and antiemetic properties in the literature [4,5]. The well-known use of 1,3,4-oxadiazole derivatives as a scaffold in modern medicinal chemistry [6], as verified by these specimens, establishes this moiety as a member of the prosperous structures course.…”

Quantitative structure activity relationship (QSAR) studies of a series of 2,5-disubstituted-1,3,4-oxadiazole derivatives as biologically potential compounds

“…In the past (Shi et al 2001;Soni et al 2004;Zou et al 2002) some efforts have been made to understand the structure-activity relationships of a series of novel 5-[1-aryl-1,4-dihydro-6-methylpyridazin-4-one-3-yl]-2-arylamino-1,3,4-oxadiazoles for their fungicidal activity and oxadiazole substituted a-isopropoxy phenylpropionic acids as PPAR-a and PPAR-c agonists using 2-D and 3-D QSAR techniques like regression analysis and COMFA, respectively. In the view of our continued interest in the oxadiazole chemistry, we have reported (Somani et al 2008a, b, c) the synthesis and anti-bacterial activity of some novel series of 2-(N,N-disubstituted acetamido)-5-pyridyl-1,3,4-oxadiazol-2-thiol, (Series 1; 1-9) (Somani et al 2008a), 2-(N,N-disubstituted propionamido)-5-pyridyl-1,3,4-oxadiazol-2-thiol (Series 1; 10-18) (Somani et al 2008b), 2-(N-arylsubstituted acetamido)-5-(1,2,3-benztriazolylmethyl)-1,3,4-oxadiazol-2-thiol (Series 2; 19-27) and 2-(N-arylsubstituted propionamido)-5-(1,2,3-benztriazolylmethyl)-1,3,4-oxadiazol-2-thiol (Series 2; 28-36) (Somani et al 2008c). Our thrust for the search of some newer and potent anti-bacterial agents, which is driven by the fact that drug resistance is the major problem in treatment of infectious diseases, prompted us to carry out QSAR studies of the molecules mentioned in above series.…”