Synthesis and characterization of new 4-aryl-2-(2-oxopropoxy)-6-(2,5-dichlorothiophene)nicotinonitrile and their furo[2,3-b]pyridine derivatives: Assessment of antioxidant and biological activity
Open Access
- 31 December 2018
- journal article
- Published by European Journal of Chemistry in European Journal of Chemistry
Abstract
A new series of furo[2,3-b]pyridine derivatives bearing aryl substituents were synthesized in two steps, where, the cyano-(2H)-pyridones (1a-l) were converted to the corresponding nicotinonitriles (2a-l), followed by the Thorpe-Ziegler ring cyclization to the furo[2,3-b]pyridine derivatives (3a-l). All new compounds were characterized by 1D-NMR experiments (1H and 13C) and 2D-NMR experiments (COSY, HMBC and HSQC), as well as ESI-MS and HR-ESI-MS data. The new compounds were screened for their antioxidant activities by 2,2-diphenyl-1-picryl-hydrazylhydrate (DPPH) free radical assay. The highest radical scavenging effect was observed for nicotinonitriles 2d, 2h and 2l and furo[2,3-b]pyridines 3b, 3f and 3j by methanolic solvent at 4.0 mg/mL concentration. Remarkably, all nicotinonitriles and furo[2,3-b]pyridine exhibited a significant radical scavenging activity after 24 and 48 hours compared with 0.5 hour.Keywords
This publication has 21 references indexed in Scilit:
- Synthesis, Antimicrobial and Antioxidant Activity of Chalcone Derivatives Containing Thiobarbitone NucleusMedicinal Chemistry, 2016
- Synthesis of novel trifluoromethyl substituted furo[2,3- b ]pyridine and pyrido[3′,2′:4,5]furo[3,2- d ]pyrimidine derivatives as potential anticancer agentsEuropean Journal of Medicinal Chemistry, 2016
- Substituted furopyridinediones as novel inhibitors of α-glucosidaseRSC Advances, 2015
- Synthesis, transformations and biological properties of furo[2,3-b]pyridinesRussian Chemical Reviews, 2015
- Synthesis, biological evaluation, and docking studies of novel heterocyclic diaryl compounds as selective COX-2 inhibitorsBioorganic & Medicinal Chemistry, 2010
- Free radicals and antioxidants in normal physiological functions and human diseaseThe International Journal of Biochemistry & Cell Biology, 2007
- Furomegistines I and II, two furanopyridine alkaloids from the bark of Sarcomelicope megistophyllaPhytochemistry, 2001
- Identification of MK-944a: A Second Clinical Candidate from the Hydroxylaminepentanamide Isostere Series of HIV Protease InhibitorsJournal of Medicinal Chemistry, 2000
- Studies on 8-Methoxyquinolones: Synthesis and Antibacterial Activity of 7-(3-Amino-4-substituted)pyrrolidinyl Derivatives.CHEMICAL & PHARMACEUTICAL BULLETIN, 2000
- Potent non-6-fluoro-substituted quinolone antibacterials: synthesis and biological activityJournal of Medicinal Chemistry, 1992