Abstract
In this paper, we reported the synthesis of coumarin-pyrimidine derivatives by a four-component reaction involving 4-hydroxycoumarin, aldehyde, thiobarbituric acid and piperidine in ethanol. All the synthesized compounds were well-characterized by IR, NMR and mass spectroscopic techniques. Further, to evaluate the biological potency of the synthesized compounds, initially, DNA cleavage studies were performed. Encouraged by the results obtained from the cleavage studies, the synthesized compounds were screened for in-vitro antibacterial and anti-inflammatory activity. From the biological activity results, it revealed that most of the synthesized compounds were found to exhibit potent antimicrobial and anti-inflammatory activity with least IC50 than compared with standard.
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References
Li S, Yu A, Li J and Meng X 2019 Synthesis of Benzothiophene-Fused Pyran Derivatives via Piperidine Promoted Domino Reaction Hetero. Chem. 2019
Kumar K A, Renuka N, Kumar G V and Lokeshwari D M 2015 Pyrans: Heterocycles of chemical and biological interest J. Chem. Pharma. Res. 47 693
Dar A M and Mir S 2017 Molecular Docking: Approaches, Types, Applications and Basic Challenges J. Anal. Bioanal. Tech. 8 1000356
Gunathilake K D P P, Ranaweera K K D S and Vasantha Rupasinghe H P 2018 In Vitro Anti-Inflammatory Properties of Selected Green Leafy Vegetables Biomedicines 6 107
Kayal G, Kayal S, Gokhale N and Jain S 2016 Synthesis and biological evaluation of coumarin derivatives as anti-inflammatory agents Int. J. Pharm. Sci. Res. 7 2394
Reddy J S, Richard L, Prasanthi D, Shreedhara C S and Pai A 2017 Investigation of Anti-Inflammatory Potentials of Terminalia Tomentosa Wight & Arn. Bark - An In-Vitro Approach J. Glob. Pharm. Tech. 08 01
Balakumar C, Lamba P, Pran Kishore D, Lakshmi Narayana B, Venkat Rao K, Rajwinder, K, Raghuram Rao A, Shireesha B and Narsaiah B 2010 Synthesis, anti-inflammatory evaluation and docking studies of some new fluorinated fused quinazolines Eur. J. Med. Chem. 45 4904
Sangeetha G and Vidhya R 2016 In vitro anti-inflammatory activity of different parts of Pedalium murex (L.) Int. J. Herb. Med. 4 31
Okada F 2002 Inflammation and free radicals in tumor development and progression Redox Rep 7 357
Lu H, Ouyang W and Huang C 2004 Inflammation, a Key Event in Cancer Development Mol. Cancer. Res. 4 221
Tatti P N, Anitha S, Shashidhara S, Deepak M and Sanjeevkumar B 2012 Evaluation of in-vitro anti-denaturation activity of isolated compound of Butea Monosperma Bark Int. J. Pharm. Sci. 3 2314
Subbaiyan S, Ganesan A and Chinnasamy J 2014 Synthesis, spectral, DNA binding and cleavage properties of ruthenium (II) Schiff base complexes containing PPh3/AsPh3 as co-ligands J. Serb. Chem. Soc. 79 151
Kambappa V, Chandrashekara G K, Rekha N D, Shivaramu, P D and Palle K 2017 Synthesis, anti-angiogenic and DNA cleavage studies of novel N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)piperidine-4-carboxamide derivatives Chem. Central. J. 122 1
Reddy D S, Hosamani K M and Devarajegowda H C 2015 Design, synthesis of benzocoumarin-pyrimidine hybrids as novel class of antitubercular agents, their DNA cleavage and X-ray studies Eur. J. Med. Chem. 101 705
Anbu S, Muthusamy K and Varghese B 2010 Structural, electrochemical, phosphate-hydrolysis, DNA binding and cleavage studies of new macrocyclic binuclear nickel (II) complexes Dalton Trans. 39 3823
Allali M, Benjelloun G T, Chahboun N, Mouacha Y, Allali N, Bennani L, Ouahidi I, Ibijbijen J and Nassiri L 2017 Synthesis, characterization and the antibacterial activity of a new [1,2,3]triazole derivative J. Mater. Environ. Sci. 8 2916
Rahman H, Eswaraiah M C and Dutta A M 2015 In-vitro antiinflammatory and anti-arthritic activity of Oriza sativa Var. Joha Rice (An Aromatic Indigenous Rice of Assam) Am.-Eur. J. Agri. Environ. Sci. 15 115
Saleem T M, Azeem K, Dilip C, Sankar C, Prasanth N and Duraisami R 2011 Anti-inflammatory activity of the leaf extacts of Gendarussa vulgaris Nees Asian. Pac. J. Trop. Biomed. 1 147
Sharma P, Rane N and Gurram V 2004 Synthesis and QSAR studies of pyrimido[4,5-d]pyrimidine-2,5-dione derivatives as potential antimicrobial agents Bioorg. Med. Chem. Lett. 14 4185
Dhorajiya B D, Bhakhar B S and Dholakiya B Z 2012 Synthesis, characterization, solvato chromic properties and antimicrobial evaluation of 5-acetyl-2-thioxo-dihydropyrimidine-4, 6-dionebased chalcones Med. Chem. Res. 22 4075
Malik I, Csollei J, Jampilek J, Stanzel L, Zadrazilova I, Hosek J, Pospisilova S, Cizek, Aidan C A and Mahony J O 2016 The Structure–Antimicrobial Activity Relationships of a Promising Class of the Compounds Containing the N-Arylpiperazine Scaffold Molecules 21 1274
Jeschke P 2010 The unique role of halogen substituents in the design of modern agrochemicals Pest. Manag. Sci. 66 10
Bhat A R, Dongre R S, Shalla A H, Naikoo G A and Hassan I U 2016 Computational analysis for antimicrobial active pyrano[2,3-d]pyrimidine derivatives on the basis of theoretical and experimental ground J. Assoc. Arab Univ. Basic Appl. Sci. 20 19
Aly H M, Kamal M M 2012 Efficient one-pot preparation of novel fused chromeno[2,3-d]pyrimidine and pyrano[2,3-d]pyrimidine derivatives Eur. J. Med. Chem. 47 18
Roy S, Nandi R K, Ganai S, Majumdar K C and Das T K 2017 Binding interaction of phosphorus heterocycles with bovine serum albumin. A biochemical study J. Pharm. Ana. 7 9
Bailey-Shaw Y A, Williams L A D, Green C E, Rodney S and Smith A M 2017 In-Vitro Evaluation of the Anti-Inflammatory Potential of Selected Jamaican Plant Extracts using the Bovine Serum Albumin Protein Denaturation Assay Int. J. Pharm. Sci. Rev. Res. 47 145
Asirvatham S, Dhokchawle B V and Tauro S J 2016 Quantitative structure activity relationships studies of non-steroidal anti-inflammatory drugs: A review Arab. J. Chem. 12 3948
Arora R K, Kaur N, Bansal Y and Bansal G 2014 Novel coumarin–benzimidazole derivatives as antioxidants and safer anti-inflammatory agents Acta Pharm. Sinica. B 4 368
Lokwani D K, Mokale S N and Shinde D B 2014 3D QSAR studies based in silico screening of 4,5,6-triphenyl-1,2,3,4-tetrahydropyrimidine analogs for anti-inflammatory activity Eur. J. Med. Chem. 73 233
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One of the authors would like to acknowledge the Chairman, Department of Industrial Chemistry, Kuvempu University, Shankaraghatta for providing laboratory facilities.
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Naik, M.D., Bodke, Y.D., Prashantha, J. et al. A facile one-pot synthesis of 1H-pyrano[2,3-d]pyrimidin-4(5H)-ones and evaluation of their Ct-DNA interaction, antibacterial and anti-inflammatory activity. J Chem Sci 133, 17 (2021). https://doi.org/10.1007/s12039-020-01875-1
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DOI: https://doi.org/10.1007/s12039-020-01875-1