synthesis and characterization of Pyrimidine from chalcone as a polymeric prodrug with fusidic acid and ZnO and study bioactivity
Main Article Content
Keywords
chalcone as a polymeric prodrug, Pyrimidine, fusidic acid, ZnO
Abstract
Pyrimidine was synthesized as a derivative of chalcone, then polymerization of pyrimidine was carried out with fusidic acid and zinc oxide. All the physical properties affecting the construction process, such as Thin-layer chromatography, solubility, the effect of buffer solutions, and temperatures, were studied. Physical diagnostics such as DSC, TGA, and FT-IR were also studied. The study of the
biological activity of the polymer resulting from the interaction of pyrimidine with fusidic acid and zinc oxide, where the study was conducted against three types of bacteria, and the results of the study were compared with the study of fusidic acid alone once and with zinc oxide alone again as a control. The results showed that the process of polymerization of pyrimidine with fusidic acid and zinc oxide gave more effective results against bacteria compared to fusidic acid alone and zinc oxide alone.
References
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28. Ng H, Saidi NM, Omar FS, Ramesh K, Ramesh S, Bashir S. Thermogravimetric analysis of polymers. Encyclopedia of polymer science and technology. 2002:1-29.
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30. Ternavisk RR, Camargo AJ, Machado FB, Rocco JA, Aquino GL, Silva VH, et al. Synthesis, characterization, and computational study of a new dimethoxy-chalcone. Journal of molecular modeling. 2014;20:1-11.
31. Mallikarjunaswamy C, Mallesha L, Bhadregowda D, Pinto O. Studies on synthesis of pyrimidine derivatives and their antimicrobial activity. Arabian Journal of Chemistry. 2017;10:S484-S90.
32. Ali ET, Al-Salman H, Rasool KH, Jabir MS, Ghimire TR, Shari FH, et al. 2-(Benzhydryl sulfinyl)-N-sec-butylacetamide) isolated from fig augmented trastuzumab-triggered phagocytic killing of cancer cells through interface with Fcγ receptor. Natural Product Research. 2023:1-9.
33. AL-Salman HN, Ali ET, Almukhtar OA, Jabir MS, editors. 2-benzhydrylsulfinyl-N-hydroxyacetamide extracted from fig: A good therapeutic agent against Staphylococcus aureus. AIP Conference Proceedings; 2020: AIP Publishing LLC.
34. Al-Salman H, Ali ET, Jabir M, Sulaiman GM, Al-Jadaan SA. 2-Benzhydrylsulfinyl-N-hydroxyacetamide-Na extracted from fig as a novel cytotoxic and apoptosis inducer in SKOV-3 and AMJ-13 cell lines via P53 and caspase-8 pathway. European Food Research and Technology. 2020;246:1591-608.
35. Al-Bahadily DC, Alkamil RD, Qasim QA, Shari FH, Al-Salman H. Analytical and biological sctivitystudy of one of the isolated extracts of Tuffles ethyl 6-Methyl-2-oxo-4-(2-Thenyl)-1, 2, 3, 4-tetrahydroperimidine-5-carboxylate (EMOTTC) against three of candida species. 2020.
36. Organization WH. Promoting rational use of medicines: core components. World Health Organization, 2002.
37. Mayclin SJ. Structural and Functional Characterization of the LPS Transport Complex LptDE from Pathogenic Gram-negative Bacteria: New York University; 2015.
38. Normark BH, Normark S. Evolution and spread of antibiotic resistance. Journal of internal medicine. 2002;252(2):91-106.
39. Bansal R, Singh R. Steroidal pyrazolines as a promising scaffold in drug discovery. Future Medicinal Chemistry. 2020;12(10):949-59.
40. Xie J, Schaich K. Re-evaluation of the 2, 2-diphenyl-1-picrylhydrazyl free radical (DPPH) assay for antioxidant activity. Journal of agricultural and food chemistry. 2014;62(19):4251-60.36-
41. Xu Y, Jin FQ, Huang WY. Facile nucleophilic addition of thiols to 1,1-difluoroallene: a convenient approach to γ,γ-difluoroallyl sulphides. J. Fluorine Chem; 70: 5–6 1995.
42. Kappe CO. Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog. Acc. Chem. Res. 33(12): 879–888. 2000.
43. Monier M, Abdel-Latif D, El-Mekabaty A, Elattar KM. Bicyclic 6 + 6 systems: advances in the chemistry of heterocyclic compounds incorporated pyrimido [1, 2-a] pyrimidine skeleton. Mini Rev. Org. Chem; 17(6): 717–739.2020.
44. Irena K, Petar YA. Antioxidant Properties of Pyrimidine and Uracil Derivatives. Current Organic Chemistry; 21: 2096-2108. 2017.
45. Zheng Chen, Riccardo Bertin, Guglielmina Froldi. EC50 estimation of antioxidant activity in DPPH radical dot assay using several statistical programs. Food Chemistry; 138(1): 414-420. 2013.
46. Zhivko A. Velkova, Mikhail K. Kolevb, Alia V. Tadjer. Modeling and Statistical Analysis of DPPH Scavenging Activity of Phenolics. Collect. Czech. Chem. Commun;, 72: 1461-1471. 2007.
47. Knudsen LF, Curtis JM. The use of the angular transformation in biological assays. Journal of the American Statistical Association;. 42(238): 282–296. 1947.
48. Sruthi S, Millot N, Mohanan P. Zinc oxide nanoparticles mediated cytotoxicity, mitochondrial membrane potential and level of antioxidants in presence of melatonin. International journal of biological macromolecules. 2017;103:808-18.
49. Singh TA, Sharma A, Tejwan N, Ghosh N, Das J, Sil PC. A state of the art review on the synthesis, antibacterial, antioxidant, antidiabetic and tissue regeneration activities of zinc oxide nanoparticles. Advances in Colloid and Interface Science. 2021;295:102495.
2. Elkanzi NA, Hrichi H, Alolayan RA, Derafa W, Zahou FM, Bakr RB. Synthesis of chalcones derivatives and their biological activities: a review. ACS omega. 2022;7(32):27769-86.
3. MT Albuquerque H, MM Santos C, AS Cavaleiro J, MS Silva A. Chalcones as Versatile Synthons for the Synthesis of 5-and 6-membered Nitrogen Heterocycles. Current Organic Chemistry. 2014;18(21):2750-75..
4. Dhaliwal JS, Moshawih S, Goh KW, Loy MJ, Hossain MS, Hermansyah A, et al. Pharmacotherapeutics applications and chemistry of chalcone derivatives. Molecules. 2022;27(20):7062
5. Sahu M, Siddiqui N. A review on biological importance of pyrimidines in the new era. Int J Pharm Pharm Sci. 2016;8(5):8-21.
6. Mohana Roopan S, Sompalle R. Synthetic chemistry of pyrimidines and fused pyrimidines: A review. Synthetic Communications. 2016;46(8):645-72.
7. Zarenezhad E, Farjam M, Iraji A. Synthesis and biological activity of pyrimidines-containing hybrids: Focusing on pharmacological application. Journal of Molecular Structure. 2021;1230:129833
8. Shaaban OG, Issa DA, El-Tombary AA, Abd El Wahab SM, Wahab AEA, Abdelwahab IA. Synthesis and molecular docking study of some 3, 4-dihydrothieno [2, 3-d] pyrimidine derivatives as potential antimicrobial agents. Bioorganic Chemistry. 2019;88:102934
9. Saber AF, Kamal El‐Dean AM, Redwan SM, Zaki RM. Synthesis, spectroscopic characterization, and in vitro antimicrobial activity of fused pyrazolo [4′, 3′: 4, 5] thieno [3, 2‐d] pyrimidine. Journal of the Chinese Chemical Society. 2020;67(7):1239-46.
10. Kostova I, Atanasov PY. Antioxidant Properties of Pyrimidine and Uracil Derivatives. Current Organic Chemistry. 2017;21(20):2096-108.
11. Kumar S, Narasimhan B. Therapeutic potential of heterocyclic pyrimidine scaffolds. Chemistry Central Journal. 2018;12(1):1-29.
12. Bano T, Kumar N, Dudhe R. Free radical scavenging properties of pyrimidine derivatives. Organic and medicinal chemistry letters. 2012;2(1):1-6.
13. Nair N, Majeed J, Sweety R, Thakur R. Antioxidant Potential of Pyrimidine Derivatives against Oxidative Stress. Indian Journal of Pharmaceutical Sciences. 2022;84(1):14-26.
14. Hricovíniová J, Kozics K. Screening the protective and antioxidant potential of C-2, N-3 ring-substituted quinazolinones.
15. Nabi B, Rehman S, Baboota S, Ali J. Natural antileprotic agents: a boon for the management of leprosy. Discovery and Development of Therapeutics from Natural Products Against Neglected Tropical Diseases: Elsevier; 2019. p. 351-72
16. Eid AM, Istateyeh I, Salhi N, Istateyeh T. Antibacterial activity of Fusidic acid and sodium Fusidate nanoparticles incorporated in pine oil Nanoemulgel. International Journal of Nanomedicine. 2019:9411-21.
17. Babayevska N, Przysiecka Ł, Iatsunskyi I, Nowaczyk G, Jarek M, Janiszewska E, et al. ZnO size and shape effect on antibacterial activity and cytotoxicity profile. Scientific Reports. 2022;12(1):8148.
18. Sulaiman VY, Sheat Am. Synthesis Of Alpha, Beta Unsaturated Cyclic Ketones Via Robinson Annulation Reaction. Journal of Pharmaceutical Negative Results. 2022:3294-302.
19. Mistry RN, Desai K. Studies on synthesis of some novel heterocyclic chalcone, pyrazoline, pyrimidine-2-one, pyrimidine-2-thione, para-acetanilide sulphonyl and benzoyl derivatives and their antimicrobial activity. E-Journal of Chemistry. 2005;2(1):30-41.
20. Tyunina EY, Badelin VG, Mezhevoi IN. Observation of complex formation between L-histidine and heterocyclic compounds in water and aqueous buffer solution using calorimetric and spectroscopic methods. Journal of Molecular Liquids. 2019;278:505-11
21. Elkanzi NA, Hrichi H, Alolayan RA, Derafa W, Zahou FM, Bakr RB. Synthesis of chalcones derivatives and their biological activities: a review. ACS omega. 2022;7(32):27769-86.
22. Susanti V, Setyowati W, editors. Synthesis and Characterization of Some Bromochalcones Derivatives. IOP Conference Series: Materials Science and Engineering; 2019: IOP Publishing.
23. Jawad AM, Salih MNM, Helal TA, Obaid NH, Aljamali NM. Review on chalcone (preparation, reactions, medical and bio applications). International Journal of Chemical Synthesis and Chemical Reactions. 2019;5(1):16-27.
24. Abd El-Sattar NE, Badawy EH, Abdel-Mottaleb M. Synthesis of some Pyrimidine, Pyrazole, and Pyridine derivatives and their reactivity descriptors. Journal of Chemistry. 2018;2018:1-11.
25. Lamie PF, Philoppes JN. 2-Thiopyrimidine/chalcone hybrids: design, synthesis, ADMET prediction, and anticancer evaluation as STAT3/STAT5a inhibitors. Journal of enzyme inhibition and medicinal chemistry. 2020;35(1):864-79.
26. Ng H, Saidi NM, Omar FS, Ramesh K, Ramesh S, Bashir S. Thermogravimetric analysis of polymers. Encyclopedia of polymer science and technology. 2002:1-29.
27. Kong Y, Hay J. The measurement of the crystallinity of polymers by DSC. Polymer.2002;43(14):3873-8.
28. Ng H, Saidi NM, Omar FS, Ramesh K, Ramesh S, Bashir S. Thermogravimetric analysis of polymers. Encyclopedia of polymer science and technology. 2002:1-29.
29. Price DM, Hourston DJ, Dumont F. Thermogravimetry of polymers. Encyclopedia of analytical chemistry. 2000:8094-105.
30. Ternavisk RR, Camargo AJ, Machado FB, Rocco JA, Aquino GL, Silva VH, et al. Synthesis, characterization, and computational study of a new dimethoxy-chalcone. Journal of molecular modeling. 2014;20:1-11.
31. Mallikarjunaswamy C, Mallesha L, Bhadregowda D, Pinto O. Studies on synthesis of pyrimidine derivatives and their antimicrobial activity. Arabian Journal of Chemistry. 2017;10:S484-S90.
32. Ali ET, Al-Salman H, Rasool KH, Jabir MS, Ghimire TR, Shari FH, et al. 2-(Benzhydryl sulfinyl)-N-sec-butylacetamide) isolated from fig augmented trastuzumab-triggered phagocytic killing of cancer cells through interface with Fcγ receptor. Natural Product Research. 2023:1-9.
33. AL-Salman HN, Ali ET, Almukhtar OA, Jabir MS, editors. 2-benzhydrylsulfinyl-N-hydroxyacetamide extracted from fig: A good therapeutic agent against Staphylococcus aureus. AIP Conference Proceedings; 2020: AIP Publishing LLC.
34. Al-Salman H, Ali ET, Jabir M, Sulaiman GM, Al-Jadaan SA. 2-Benzhydrylsulfinyl-N-hydroxyacetamide-Na extracted from fig as a novel cytotoxic and apoptosis inducer in SKOV-3 and AMJ-13 cell lines via P53 and caspase-8 pathway. European Food Research and Technology. 2020;246:1591-608.
35. Al-Bahadily DC, Alkamil RD, Qasim QA, Shari FH, Al-Salman H. Analytical and biological sctivitystudy of one of the isolated extracts of Tuffles ethyl 6-Methyl-2-oxo-4-(2-Thenyl)-1, 2, 3, 4-tetrahydroperimidine-5-carboxylate (EMOTTC) against three of candida species. 2020.
36. Organization WH. Promoting rational use of medicines: core components. World Health Organization, 2002.
37. Mayclin SJ. Structural and Functional Characterization of the LPS Transport Complex LptDE from Pathogenic Gram-negative Bacteria: New York University; 2015.
38. Normark BH, Normark S. Evolution and spread of antibiotic resistance. Journal of internal medicine. 2002;252(2):91-106.
39. Bansal R, Singh R. Steroidal pyrazolines as a promising scaffold in drug discovery. Future Medicinal Chemistry. 2020;12(10):949-59.
40. Xie J, Schaich K. Re-evaluation of the 2, 2-diphenyl-1-picrylhydrazyl free radical (DPPH) assay for antioxidant activity. Journal of agricultural and food chemistry. 2014;62(19):4251-60.36-
41. Xu Y, Jin FQ, Huang WY. Facile nucleophilic addition of thiols to 1,1-difluoroallene: a convenient approach to γ,γ-difluoroallyl sulphides. J. Fluorine Chem; 70: 5–6 1995.
42. Kappe CO. Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog. Acc. Chem. Res. 33(12): 879–888. 2000.
43. Monier M, Abdel-Latif D, El-Mekabaty A, Elattar KM. Bicyclic 6 + 6 systems: advances in the chemistry of heterocyclic compounds incorporated pyrimido [1, 2-a] pyrimidine skeleton. Mini Rev. Org. Chem; 17(6): 717–739.2020.
44. Irena K, Petar YA. Antioxidant Properties of Pyrimidine and Uracil Derivatives. Current Organic Chemistry; 21: 2096-2108. 2017.
45. Zheng Chen, Riccardo Bertin, Guglielmina Froldi. EC50 estimation of antioxidant activity in DPPH radical dot assay using several statistical programs. Food Chemistry; 138(1): 414-420. 2013.
46. Zhivko A. Velkova, Mikhail K. Kolevb, Alia V. Tadjer. Modeling and Statistical Analysis of DPPH Scavenging Activity of Phenolics. Collect. Czech. Chem. Commun;, 72: 1461-1471. 2007.
47. Knudsen LF, Curtis JM. The use of the angular transformation in biological assays. Journal of the American Statistical Association;. 42(238): 282–296. 1947.
48. Sruthi S, Millot N, Mohanan P. Zinc oxide nanoparticles mediated cytotoxicity, mitochondrial membrane potential and level of antioxidants in presence of melatonin. International journal of biological macromolecules. 2017;103:808-18.
49. Singh TA, Sharma A, Tejwan N, Ghosh N, Das J, Sil PC. A state of the art review on the synthesis, antibacterial, antioxidant, antidiabetic and tissue regeneration activities of zinc oxide nanoparticles. Advances in Colloid and Interface Science. 2021;295:102495.
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Mar 29, 2023
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Muhsn Ali hazam, Raheem Jameel Mahesein, & H. N. K. AL-Salman. (2023). synthesis and characterization of Pyrimidine from chalcone as a polymeric prodrug with fusidic acid and ZnO and study bioactivity. Journal of Population Therapeutics and Clinical Pharmacology, 30(5), 156–175. https://doi.org/10.47750/jptcp.2023.30.05.018
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