Electrosynthesis and screening of novel 1,3,4-oxadiazoles as potent and selective antifungal agents

Abstract

The electrochemical oxidation of aldehyde-N-aroylhydrazone has been studied in the presence of NaClO 4 as supporting electrolyte in MeOH solution using cyclic voltammetry and controlled potential electrolysis.The results indicate that intramolecular cyclization of aldehyde-N-aroylhydrazone has been successfully performed at a platinum electrode in an undivided cell with good yields of the corresponding 1,3,4oxadiazoles at ambient conditions. The reaction products were characterized by spectroscopic methods and a mechanism was deduced from voltammetry studies. The antifungal activity of the synthesized compounds was evaluated on Fusarium oxysporum, Alternaria solani, Candida albicans and Aspergillus niger. The results revealed that all the synthesized compounds have significant antifungal activity against the tested fungi. Among the synthesized derivatives 7b, 7d, 7g, 7h, 7i, 7j and 7r were found to be the most effective antifungal compounds.

Recent advances on oxadiazole motifs: Synthesis, reactions and biological activities

“…After optimization, it was revealed that carrying out the reaction in methanol using NaClO4 as supporting electrolyte gave the highest yields. Good to excellent yields ranging from 57% to 94% were obtained 65 . 34 .…”

One‐pot three‐component synthesis of chromeno [2,3‐d] pyrimidine derivatives: Novel, simple, and efficient electrochemical approach

“…A 50‐mL beaker‐type cell consists of a mixture of aromatic aldehyde (2 mmol), barbituric acid (2 mmol), and 1,3 dicarbonyl compounds (2 mmol) (Scheme ) stirred in water media with tetrabutylammonium iodide (1 mmol) as an electrolyte under constant potential electrolysis at room temperature for 1‐ to 2‐hour assembly with platinum plates (1 cm 2 ) as working as well as counter electrodes and an SCE as reference electrode. The completion of the reaction was confirmed by thin‐layer chromatography (TLC) plate at regular breaks of time.…”

Synthesis of 2,5‐Disubstituted‐1,3,4‐oxadiazole Derivatives and Their Evaluation as Anticancer and Antimycobacterial Agents

“…Literature is flooded with the construction of this scaffold and nearly 686 patents have been filed since last decade thus highlighting/capturing accelerated interest from several research groups due to the myriad applications of this system . Symmetrically and unsymmetrically 2,5‐disubstituted‐1,3,4‐oxadiazoles are encompassed with an array of broad spectrum of activities such as analgesic, antidiabetic, anticancer, antifungal, anti‐inflammatory, antitubercular, antibacterial, antiepileptic, anti‐HIV, ulcerogenic, hypoglycemic, sedative, hypnotic and insecticidal agents . Further, oxadiazoles serves as very good bioisosteres of esters, amides which makes better hydrogen bonding interactions with different receptors thereby enhancing the biological responses to a remarkable extent and resistant to enzyme‐catalyzed hydrolysis .…”