Design and synthesis of novel 1, 3, 2-benzoxazaphosphinine-2-one derivatives: an in vitro biological evaluation and in silico approaches. (6th January 2021)

• Record Type: Journal Article
• Authors: Sivala, Munichandra Reddy; Chintha, Venkataramaiah; Potla, Krishna Murthy; Kerru, Nagaraju; Chinnam, Sivakoteswararao; Devineni, Subba Rao; Salam J. J., Titinchi; Chinnam, Sampath; Chamarthi, Naga Raju
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 196:Number 6(2021)
• Page Start: 548
• Page End: 558
• Publication Date: 2021-01-06
• Subjects: Organophosphorus heterocycles -- 1, 3, 2-benzoxazaphosphinine-2-ones -- anti-fungal activity -- antioxidant activity -- molecular docking; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2020.1871346
• Languages: English
• ISSNs: 1042-6507

Abstract

Abstract: A new class of benzoxazaphosphinine-2-one derivatives were synthesized by the reaction of 2-(3a, 4, 5, 6, 7, 7a-hexahydro-1 H -benzo[ d ]imidazol-2-yl)phenol with salicylic acid and thionyl chloride (SOCl2 ) via three-step process, and were obtained in good to excellent yields (77–95%) The designed compounds were evaluated for their in vitro antioxidant, anti-fungal activities and in silico molecular docking. Amongst all, five compounds exhibited significant anti-fungal activity against F. oxysporum, A. niger and A. foetidus with MIC values displaying from 3.12 to 6.25 µg/mL correlated with standard drug Ketoconazole at 200 µg/mL. Furthermore, four compounds displayed promising antioxidant activity compared with the standard drugs butylated hydroxytoluene (BHT) and ascorbic acid in 1, 1-diphenyl-2-picrylhydrazyl (DPPH) and nitric oxide (NO) methods at 25, 50, 75 and 100 µg/mL. Molecular docking results disclosed that all the title compounds shown interesting binding modes with docking scores between −6.6 and −7.8 against the target 3MNG protein in comparison with standard drugs BHT (−5.1) and ascorbic acid (−5.5). Graphical abstract: