Synthesis, In-vitro Antioxidant, Anti-diabetic Evaluation and Docking Studies of Newly Synthesized Benzoxazole Derivatives

Abstract

In the present study, a set of different benzoxazole derivatives has been synthesized from ethyl acetoacetate, ethoxymethylene malononitrile, NaNO2, and organic acids. Analytical instruments like proton NMR (1H), carbon NMR (13C), infrared spectroscopy (IR), and LC-MS mass spectrometry were used for structural characterization. Synthesized molecules were evaluated for In-vitro antioxidant property (DPPH assay, Total antioxidant & reducing power method) and anti-diabetic property (alpha-amylase & alpha-glucosidase assay). In silico, studies against Human pancreatic alpha-amylase (PDB ID: 3BAW) have been carried out to get the binding approach of the ligand towards the protein. The results demonstrated that compounds namely 5b, 6b, 3b and 4b had potent antioxidant and anti-diabetic activity compared with ascorbic acid and acarbose. HIGHLIGHTS Anti-oxidant (DPPH assay, Total antioxidant and Reducing power) and Anti-diabetic (alpha-amylase & alpha-glucosidase assay) activities performed for synthesized molecules Sulfonamide substitutions are more potent towards biological activities In silico docking studies correlate with in vitro studies The small three-dimensional, stable structure and its ability to form hydrogen bonding the molecules show good activity towards antioxidant and anti-diabetic GRAPHICAL ABSTRACT

Advances in the synthetic strategies of benzoxazoles using 2-aminophenol as a precursor: an up-to-date review

“…Kadagathur et al 81 designed an easy, greener, and procient pathway for the synthesis of benzoxazole (18) analogs by the cyclo desulfurization reaction of 2-aminophenol (1), isothiocyanates (17), and 30% H 2 O 2 in water as an oxidant in ethanol under microwave irradiation for 10 min at 100 °C. Ease of operation, cleaner reaction proles, high yield of products (88-98%), short reaction time, and the use of a green solvent made this an eco-benign protocol (Scheme 14).…”

“…It is an overarching framework of numerous biologically active compounds that are involved in synthetic, agrochemical, pharmaceutical, and material chemistry. 13,14 This skeleton is prominent in synthetic compounds and exhibits a broad range of biological activities, such as antimicrobial, 15 antitubercular, 16 antioxidant, 17 antifungal, 18 anti-inammatory, 19 anti-allergic, 20 antihyperglycemic, 21 antidepressant, 22 cytotoxic agents, 23,24 anticonvulsant, 25 and analgesic agents. 26 They are isosteres of the nucleic acid bases guanine and adenine that help them to easily interact with biological receptors in the human body.…”