Design, synthesis, and biological activities of novel azole-bonded $$\upbeta $$ β -hydroxypropyl oxime O-ethers

Abstract

The synthesis and biological effects of 15 novel azole-bonded β-hydroxypropyl oxime O-ethers have been described. In this synthesis, the oximation of aromatic ketones followed by an O-alkylation reaction with epichlorohydrin and/or epibromohydrin led to the corresponding O-oxime ether adducts. Subsequently, the attained O-oxime ether adducts were used to synthesize the target molecules after treating them with the appropriate azole derivatives. The in vitro antifungal and antibacterial activities of title compounds were obtained against several pathogenic fungi, Gram-positive and/or Gram-negative bacteria. Benzophenone O-2-hydroxy-3-(2-phenyl-1 H-imidazol-1-yl) propyl oxime and 9H-fluoren-9-one O-2-hydroxy-3-(2-phenyl-1 H-imidazol-1-yl)propyl oxime proved to have considerable antifungal activity against Candida albicans, Candida krusei, Aspergillus niger, and Trichophyton rubrum. These two compounds demonstrated comparable antifungal activity to clotrimazole and fluconazole (standard drugs). All compounds were also tested against Escherichia coli and Staphylococcus aureus as Gram-negative and Gram-positive bacteria, respectively, and their activities were compared to gentamycin and ampicillin (reference drugs). In general, marginal antibacterial activity against tested bacteria was observed for the title compounds. A molecular docking study is also discussed for the two most potent compounds against fungi. The docking study reveals a considerable interaction between the two most potent compounds and the active site of Mycobacterium P450DM. Moreover, these two compounds are much strongly bound to the active site of Mycobacterium P450DM compared to fluconazole.

Antifungal Agents: Design, Synthesis, Antifungal Activity and Molecular Docking of Phloroglucinol Derivatives

“…Docking studies of all derivatives were implemented in the program AutoDock 4.2.6 [21]. The X-ray crystallographic structure of SE (PDB ID: 2AIB) was taken from PDB () and was invoked as a protein structure [22,23]. Beginning of docking, all the water and ligands were removed and the random hydrogen atoms were added.…”

Design, Synthesis, and Bioassay of Novel Compounds of Isolongifolenone Oxime Derivatives

“…Synthesis of Isolongifolenone Oxime Ether Derivatives ( 3a – 3f ). The product 3a was synthesized following the report . To a stirred soln.…”

Synthesis, Antifungal Evaluation and Molecular Docking Studies of Some Tetrazole Derivatives

“…Since the considerable therapeutic activities of N-heterocyclic compounds 70 were demonstrated and also in continuation of our interest in discovering copper(II) Schiff base complexes [71][72] and the new N-heterocyclic bioactive compounds, [73][74][75][76][77][78][79] herein we report the application of a suitable and reusable Cu(II)-curcumin complex supported on silica gel and ascorbic acid as the reducing agent. This heterogeneous catalyst system exhibits a potent catalytic activity for the synthesis of some 5-substituated-1H-tetrazole derivatives tethered to bioactive N-heterocyclic cores.…”