Synthesis of New Pyrimidine Derivatives From 3-Acetylcoumarin–Chalcone Hybrid and Evaluation Their Antimicrobial Activitغe their antimicrobial activity y
DOI:
https://doi.org/10.31351/vol33iss1pp33-45Keywords:
Keywords: 3-coumarin-chalcone hybrid , thoiurea , pyrimidine derivatives , antimicrobial activity .Abstract
3-coumarin/chalcone B1/B2/B3 hybrids served as malleable antecedents for the development of novel bioactive pharmacophores. In this study, the matching coumarin-chalcones hybrid was obtained from 3-acetylcoumarin (comp A) via condensation with several aromatic aldehydes in ethanolic piperidine solution. To further modify these hybrids, we reacted them with thiourea in the presence of base in ethanol, yielding pyrimidine derivatives C1, C2, and C3. Their chemical characteristics and spectroscopic data were used to characterize the newly synthesized heterocyles. The antibacterial efficacy of all freshly produced compounds was tested. Compound (C3) was shown to have the highest antibacterial activity against both gram positive and gram negative bacteria, whereas compound (C2) displayed a moderate antibacterial activity and compound C1 had low activity. C1,C2,C3 were shown antifungal activity as compared to fluconazole that showed antifungal efficacy against C. ablicans.
Received:28 /11 /2022
Accepted: 19/2 /2023
References
Abduljabbar TT, Hadi MK. Synthesis, Characterization and Antibacterial Evaluation of Some Coumarin Derivatives. Iraqi J Pharm Sci. 2021;30(1):249–57.
Kumer A, Kobir ME, Alam M, Chakma U, Akter P, Bhuiyan MMH. Antibacterial, antifungal and antiviral activities of pyrimido[4,5-d]pyrimidine derivatives through computational approaches. Org Commun. 2022;(3):239–60.
Ahmed MH, El-Hashash MA, Marzouk MI, El-Naggar AM. Design, Synthesis, and Biological Evaluation of Novel Pyrazole, Oxazole, and Pyridine Derivatives as Potential Anticancer Agents Using Mixed Chalcone. J Heterocycl Chem. 2019 ;56(1):114–23.
Azam MA, Kumar B.R.P, Shalini S, Suresh B, Reddy TK, Reddy CD. Synthesis and Biological Screening of 5- {[( 4 , 6- Disubstituted pyrimidine-2-yl ) thio ] methyl } -N-phenyl-. Indian J Pharm Sci. 2008.
Sun L, Wu J, Zhang L, Luo M, Sun D. Synthesis and antifungal activities of some novel pyrimidine derivatives. Molecules. 2011;16(7):5618–28.
Nimavat K, Popat KH, Vasoya SL, Joshi H. Synthesis anticancer, antitubercular and antimicrobial activity of some new pyrimidine derivatives. Indian J Heterocycl Chem. 2003 ;12:217–20.
Adam RW, Al-Labban HMY, Kadhim IN, Aljanaby AAJ. Synthesis, characterization, and antibacterial activity of some new pyrimidine derivatives from chalcone derivatives. Drug Invent Today. 2019;11(7):1732–9.
Mahapatra A, Prasad T, Sharma T. Pyrimidine: a review on anticancer activity with key emphasis on SAR. Vol. 7, Future Journal of Pharmaceutical Sciences; 2021.
Hussain M. , Bharthi D. R. , Revanasiddappa B. , Hemanth Kumar. Synthesis and antioxidnat activity of novel 2-mercapto pyrimidine derivatives. Res J Pharm Technol. 2020;13(3):1224–6.
Pasricha S, Gahlot P. Synthetic Strategies and Biological Potential of Coumarin-Chalcone Hybrids: A New Dimension to Drug Design. Curr Org Chem. 2020;24(4):402–38.
Farhan MS, Ahmed MH. Synthesis, characterization and anti-inflammatory study of new heterocyclic coumarin derivatives. Indian J Forensic Med Toxicol. 2021;15(1):2363–9.
Turkovic N, Ivkovic B, Kotur-Stevuljevic J, Tasic M, Marković B, Vujic Z. Molecular Docking, Synthesis and anti-HIV-1 Protease Activity of Novel Chalcones. Curr Pharm Des. 2020;26(8):802–14.
Hassan MZ, Osman H, Ali MA, Ahsan MJ. Therapeutic potential of coumarins as antiviral agents. Eur J Med Chem . 2016;123:236–55.
O.Reilly ,R.A. Aggeler ,P.M Leong . Studies on the coumarin anticoagulant drugs: the pharmacodynamics of warfarin in man. J Clin Invest. 1963 ;42(10):1542–51.
de Souza SM, Delle Monache F, Smânia AJ. Antibacterial activity of coumarins. Z Naturforsch C. 2005;60(9–10):693–700.
Kostova I, Bhatia S, Grigorov P, Balkansky S, Parmar VS, Prasad AK, et al. Coumarins as antioxidants. Curr Med Chem. 2011;18(25):3929–51.
Prusty JS, Kumar A. Coumarins: antifungal effectiveness and future therapeutic scope. Mol Divers. 2020 ;24(4):1367–83.
Behera PC, Verma SM, Kumar PM, Das NB, Mishra PM, Baliarsingh S, et al. Determining the Anti-Inflammatory and Anti-Microbial Activity of Chalcone from Dalbergia sissoo Roxb. Leaves. Curr Asp Pharm Res Dev. 2021; (Vol 6): 147–54.
Koudokpon H, Armstrong N, Dougnon T V, Fah L, Hounsa E, Bankolé HS, et al. Antibacterial Activity of Chalcone and Dihydrochalcone Compounds from Uvaria chamae Roots against Multidrug-Resistant Bacteria. Biomed Res Int. 2018;1453173.
Constantinescu T, Lungu CN. Anticancer activity of natural and synthetic chalcones. Int J Mol Sci. 2021;22(21):1–33.
Murwih Alidmat M, Khairuddean M, Mohammad Norman N, Mohamed Asri AN, Mohd Suhaimi MH, Sharma G. Synthesis, characterization, docking study and biological evaluation of new chalcone, pyrazoline, and pyrimidine derivatives as potent antimalarial compounds. Arab J Chem. 2021 ;14(9).
Kumar A, Kumar S. Coumarin-Chalcone Hybrids for Biological Potentials: A Strategy of Molecular Hybridization for Drug Design. Int J Pharm Sci Rev Res. 2020;64(2):146–51.
Abdulraheem SS, Hadi MK. Synthesis and Characterization of New Coumarin Derivatives as Possible Antimicrobial Agents. Int J Drug Deliv Technol. 2021;11(4):1484–90.
Hamid JM. Synthesis, Characterization Of Various Coumarin Derivatives. J Educ Sci. 2013;26:74–82.
Patil S, Rajput S, Hospete S, Irkal S. Synthesis of coumarin-Chalcone Derivatives. 2019;12(7):46–51.
Azam MA, Kumar BRP, Shalini S, Suresh B, Reddy TK, Reddy CD. Synthesis and Biological Screening of 5-{[(4,6-Disubstituted pyrimidine-2-yl)thio]methyl}-N-phenyl-1,3,4-thiadiazol-2-amines. Indian J Pharm Sci. 2008 ;70(5):672—677.
Jabber MM, Hadi mohammed k. Synthesis, Characterization, and Antimicrobial Evaluation of new Ibuprofen Derivatives. Pakistan J Med Heal Sci. 2022;16(3):689–92.
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