Ultrasound- and Molecular Sieves-Assisted Synthesis, Molecular Docking and Antifungal Evaluation of 5-(4-(Benzyloxy)-substituted phenyl)-3-((phenylamino)methyl)-1,3,4-oxadiazole-2(3H)-thiones

Abstract

A novel series of 5-(4-(benzyloxy)substituted phenyl)-3-((phenyl amino)methyl)-1,3,4-oxadiazole-2(3H)-thione Mannich bases 6a-o were synthesized in good yield from the key compound 5-(4-(benzyloxy)phenyl)-1,3,4-oxadiazole-2(3H)-thione by aminomethylation with paraformaldehyde and substituted amines using molecular sieves and sonication as green chemistry tools. The antifungal activity of the new products was evaluated against seven human pathogenic fungal strains, namely, Candida albicans ATCC 24433, Candida albicans ATCC 10231, Candida glabrata NCYC 388, Cryptococcus neoformans ATCC 34664, Cryptococcus neoformans PRL 518, Aspergillus fumigatus NCIM 902 and Aspergillus niger ATCC 10578. The synthesized compounds 6d, 6f, 6g, 6h and 6j exhibited promising antifungal activity against the tested fungal pathogens. In molecular docking studies, derivatives 6c, 6f and 6i showed good binding at the active site of C. albicans cytochrome P450 enzyme lanosterol 14 α-demethylase. The in vitro antifungal activity results and docking studies indicated that the synthesized compounds have potential antifungal activity and can be further optimized as privileged scaffolds to design and develop potent antifungal drugs.

Natural Product‐Based Fungicides Discovery: Design, Synthesis and Antifungal Activities of Some Sarisan Analogs Containing 1,3,4‐Oxadiazole Moieties

“…Finally, 3-formylsarisan 5 was condensed with different aryl hydrazide and followed by the iodine-catalyzed oxidative cyclization to obtain a series of sarisan analogs (7a -7u) containing 1,3,4-oxadiazole at C-3 position. The structures of all target compounds were characterized by 1 H-NMR, 13 C-NMR, IR, HR-MS and melting point (m.p. ).…”

“…When crops are infected by these fungi, which are hard to control and cause serious yield reductions . 1,3,4‐Oxadiazole is an important class of N ‐heterocyclic compounds with a wide range of biological activities including antimicrobial, anticancer, antiviral, insecticidal and antifungal activities . As a part of our ongoing research aimed at the discovery and development of natural product‐based compounds with potent bioactivities, herein, in this article we have prepared a series of sarisan analogs containing 1,3,4‐oxadiazole moieties and evaluated for their antifungal activities.…”

Facile Synthesis of Novel Coumarin Derivatives, Antimicrobial Analysis, Enzyme Assay, Docking Study, ADMET Prediction and Toxicity Study

“…Due to their wide application, many efficient approaches to these compounds have been developed. In continuation of our research program [ 18 , 19 ] studying the synthesis of the novel heterocyclic compound which may be biologically active, we report herein the synthesis of some novel heterocyclic compounds incorporating a combination of coumarin, dicyclohexylamine and β-amino carbonyl pharmacophores.…”

Ultrasound Assisted Synthesis of 4-(Benzyloxy)-N-(3-chloro-2-(substitutedphenyl)-4-oxoazetidin-1-yl) Benzamide as Challenging Anti-Tubercular Scaffold

“…The starting material methyl 4-(benzyloxy) benzoate 3 was synthesized by the reaction of benzyl chloride 1 and methyl 4-hydroxybenzoate 2 in potassium carbonate as a catalyst in solvent N , N dimethyl formamide, in an ultra-sonicator up to 4 h [ 51 ]. The compound 3 obtained in good yield in step I was treated further with hydrazine hydrate to get 4-(benzyloxy) benzohydrazide 4 .…”