DESIGN, SYNTHESIS, AND CHARACTERIZATION OF THE SOME NOVEL 2‐AMINO-PYRIDINE‐3‐ CARBONITRILE AND 2‐AMINO-4H-PYRAN‐3‐CARBONITRILE DERIVATIVES AGAINST ANTIMICROBIAL ACTIVITY AND ANTIOXIDANT ACTIVITY
DOI:
https://doi.org/10.22159/ajpcr.2020.v13i12.39745Keywords:
Dihydrofolic reductase, 2-amino-3- cyanopyridine compounds, 2-amino-3- cyanopyrans compounds, Zone of inhibitionAbstract
Objective: Investigation, the series of newer 2‐amino-pyridine‐3‐carbonitrile and 2‐amino-4H-pyran‐3‐carbonitrile derivative were synthesized and evaluated antimicrobial activities and antioxidant activity.
Methods: Novel synthesized chalcones were further condensation to give 2-amino-3-cyanopyridine and 2-amino-3-cyanopyrans in the presence of malononitrile, pyridine, and ammonia acetate. The product is characterized by conventional and instrumental methods. Pyridine and 4-H-Pyran and their analogs occupy prime position due to their diverse applications.
Results: The compounds A3C and B3C exhibited marked zone of inhibition with 30.02±0.02 mm and 29.06±0.01 mm, respectively. Docking studies suggested possible interactions with dihydrofolic reductase 4 with 9.15 and −9.67 kcal/mol, respectively. The IC50 30.28±0.01 exhibited A3C by 2,2-diphenylpicrylhydrazyl methods which is better among the series. The 2-amino-3-cyanopyridine derivatives were found good activity than 2-amino-3-cyanopyrane derivative. Among all synthesized compounds few having potent activity and some are near to the standard.
Conclusion: Antimicrobial activity and antioxidant of the newly synthesized pyrans and pyridines derivatives will definitely inspire future researchers for the preparation of new analogs.
Downloads
References
Available from: https://www.who.int/whr/1996/media_centre/press_ release/en/index4.html.
Smith PW, Sollis SL, Howes PD, Cherry PC, Starkey ID, Cobley KN, et al. Dihydropyrancarboxamides related to zanamivir: A new series of inhibitors of influenza virus sialidases. 1. Discovery, synthesis, biological activity, and structure-activity relationships of 4-guanidino-and 4-amino-4H-pyran-6-carboxamides. J Med Chem 1998;41:787-97.
Henry GD. De novo synthesis of substituted pyridines. Tetrahedron 2004;60:6043-61.
Martínez-Grau A, Marco J. Friedländer reaction on 2-amino-3-cyano- 4H-pyrans: Synthesis of derivatives of 4H-pyran [2, 3-b] quinoline, new tacrine analogues. Bioorg Med Chem Lett 1997;7:3165-70.
Bianchi G, Tava A. Synthesis of (2R)-(+)-2,3-dihydro-2,6-dimethyl- 4H-pyran-4-one, a homologue of pheromones of a species in the Hepialidae family. Agric Biol Chem 1987;51:2001-2.
Abouzid KA, Al-Ansary GH, El-Naggar AM. Eco-friendly synthesis of novel cyanopyridine derivatives and their anticancer and PIM-1 kinase inhibitory activities. Eur J Med Chem 2017;134:357-65.
Dev S, Dhaneshwar S, Mathew B. Virtual combinatorial library design, synthesis and in vitro anticancer assessment of-2-amino- 3-cyanopyridine derivatives. Comb Chem High Throughput Scree 2018;21:138-48.
Amala VE, Jeyaraj M. Determination of antibacterial, antifungal, bioactive constituents of Triphala by FT-IR and GC-MS analysis. Int J Pharm Pharm Sci 2014;6:123-6.
Gurunanjappa P, Nagamallu R, Kariyappa AK. Synthesis and antimicrobial activity of novel fused pyrazoles. Int J Pharm Pharm Sci 2015;7:379-81.
Movassaghi M, Hill MD, Ahmad OK. Direct synthesis of pyridine derivatives. JACS 2007;129:10096-7.
Li AH, Moro S, Forsyth N, Melman N, Ji X, Jacobson KA. Synthesis, CoMFA analysis, and receptor docking of 3,5-diacyl-2,4-dialkylpyridine derivatives as selective a3 adenosine receptor antagonists. J Med Chem 1999;42:706-21.
Vacher B, Bonnaud B, Funes P, Jubault N, Koek W, Assie MB, et al. Novel derivatives of 2-pyridinemethylamine as selective, potent, and orally active agonists at 5-HT1A receptors. J Med Chem 1999;42:1648-60.
Mahdavi SM, Habibi A, Dolati H, Shahcheragh SM, Sardari S, Azerang P, et al. Synthesis and antimicrobial evaluation of 4H-pyrans and schiff bases fused 4H-pyran derivatives as inhibitors of Mycobacterium bovis (BCG). Iran J Pharm Sci 2018;17:1229.
Murata T, Shimada M, Sakakibara S, Yoshino T, Masuda T, Sato H, et al. Synthesis and structure-activity relationships of novel IKK-beta inhibitors. Part 3: Orally active anti-inflammatory agents. Bioorg Med Chem Lett 2004;14:4019-22.
Baldwin JJ, Engelhardt EL, Hirschmann R, Ponticello GS, Atkinson JG, Wasson BK, et al. Heterocyclic analogs of the antihypertensive. Beta-adrenergic blocking agent (S)-2-[3-(tert-butylamino)-2- hydroxypropoxy]-3-cyanopyridine. J Med Chem 1980;23:65-70.
Temple C Jr., Rener GA, Waud WR, Noker PE. Antimitotic agents: Structure-activity studies with some pyridine derivatives. J Med Chem 1992;35:3686-90.
Rateb NM, Zohdi HF. Atom-efficient, solvent-free, green synthesis of chalcones by grinding. Synth Commun 2009;39:2789-94.
Solankee A, Patel G, Solankee S. Synthesis and studies of chalcones and its cyanopyridine and acetyl pyrazoline derivatives. Rasayan J Chem 2008;1:591-5.
Gouda MA, Berghot MA, El Ghani GE, Khalil AE. Chemistry of 2-amino-3-cyanopyridines. Synth Commun 2014;44:297-330.
Babu LS, Shaik AB, Prasad YR. Synthesis, antibacterial, antifungal antitubercular activities and molecular docking studies of nitrophenyl derivatives. Int J Life Sci Pharma Res 2019;9:54-64.
Graziani Y, Erikson E, Erikson RL. Differential inhibitory effects of various flavonoids on the activities of reverse transcriptase and cellular DNA and RNA polymerases. Eur J Biochem 1983;135:583-9.
Protein Data Bank. Available from: http://www.rcsb.org/pdb.
Biswas NN, Acharzo AK, Anamika S, Khushi S, Bokshi B. Screening of natural bioactive metabolites and investigation of antioxidant, antimicrobial, antihyperglycemic, neuropharmacological, and cytotoxicity potentials of Litsea polyantha Juss. Ethanolic root extract. Evid Based Complement Altern Med 2017;2017:3701349.
Published
How to Cite
Issue
Section
The publication is licensed under CC By and is open access. Copyright is with author and allowed to retain publishing rights without restrictions.