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Journal of Catalyst & Catalysis Original Research

Preparation, Categorization and Anticancer Study of Novel Bicyclic Compounds from Various Types for (Five and Six)- Membered Ring

  1. Rabab Mahdi Ubaid Mahmood Teacher in Education Ministry, Almutafawkat School

Abstract

The characteristics of ring systems change in the presence of functional groups, but in some cases, elements that are considered functional groups can be classified within the same ring. Compounds that contain only carbon and hydrogen are called homogeneous rings, while those that contain other elements are called heterogeneous rings. The atom substituted in place of the carbon atom is referred to as a heteroatom. Generally, the heterocyclic atom is an oxygen, nitrogen, or sulfur atom, with nitrogen being the most common. Heterocyclic rings are vital to biological systems and are frequently found in living organisms, forming part of the molecular structure of many essential compounds. Notable examples of heterocyclic compounds include the aniline dye, several important biochemical molecules such as alkaloids, nucleotides, nucleic acids, coenzymes, and many medicinal agents including antibiotics and anticancer drugs. These structures commonly appear in five-membered, six-membered, and seven-membered ring systems. In this study, the synthesis of both monocyclic and bicyclic heterocycles was carried out, utilizing Oxadiazole and Triazole derivatives as starting materials. The reactions led to the formation of novel five-, six-, and seven-membered bicyclic ring systems with potential bioactivity. The structural elucidation of the synthesized compounds was confirmed through a series of analytical techniques, including FT-IR spectroscopy, proton nuclear magnetic resonance (^1H NMR), carbon-13 nuclear magnetic resonance (^13C NMR), and determination of melting points. Thin-layer chromatography (TLC) was used to monitor the reactions and confirm purity. Furthermore, the newly synthesized compounds were evaluated for their anticancer properties against breast cancer cell lines. The results indicated promising bioactivity, suggesting that these novel heterocyclic structures could serve as lead compounds for further pharmaceutical development.

Keywords

References (42)

  1. Albert, Adrien; Taylor, Peter J. (1989). The tautomerism of 1,2,3-triazole in aqueous solution . Journal of the Chemical Society, Perkin Transactions, 2 , 1903–1905 . doi:1039/P29890001903.
  2. Agalave, S.G.; Maujan, S.R.; Pore, V.S. (2011). Click Chemistry: 1,2,3-Triazoles as Pharmacophores, 6, 2696–2718. doi:1002/asia.201100432. PMID 21954075
  3. Jawad AAR, Aljamali DNM. Triazole-Anil and Triazol-Azo Reagents (Creation, Spectral Categorization, Scanning Microscopy, Thermal Analysis). NeuroQuantology. 2021;19(11):84-94. doi:10.14704/nq.2021.19.11.nq21178
  4. S. Ahmed F, Ahmed AH, Raad M, M. Ali APM. Isolation of ferric Yersinia bactin A (fyuA) as virulence gene and biofilm forming in Escherichia coli was Collected from patient with UTI. Al-Salam Journal for Medical Science. 2022;2(1):6-11. doi:10.55145/ajbms.2022.1.2.005
  5. Al-Daffay RKH, Al-Hamdani AAS. Synthesis and Characterization of Some Metals Complexes with New Acidicazo Ligand 4-[(2-Amino-4-Phenylazo)-Methyl]-Cyclohexane Carboxylic Acid. Iraqi Journal of Science. 2022:3264-3275. doi:10.24996/ijs.2022.63.8.2
  6. Aseel, M. J., Nagham M A .,S. M. Jawd. (2020). Development and Preparation of ciprofloxacin Drug Derivatives for Treatment of Microbial Contamination in Hospitals and Environment. IndianJournal of Forensic Medicine & Toxicology 14(2), 1115-1122.
  7. Bonandi, E.; Christodoulou, M. S.; Fumagalli, G.; Perdicchia, D.; Rastelli, G.; Passarella, D. (2017). "The 1,2,3-triazole ring as a bioisostere in medicinal chemistry". Drug Discov Today. 22(10): 1572–1581. doi:1016/j.drudis.2017.05.014. PMID 28676407.
  8. Bolje A, Urankar D, Košmrlj J. Synthesis and NMR Analysis of 1,4‐Disubstituted 1,2,3‐Triazoles Tethered to Pyridine, Pyrimidine, and Pyrazine Rings. European Journal of Organic Chemistry. 2014;2014(36):8167-8181. doi:10.1002/ejoc.201403100
  9. Virant M, Košmrlj J. Arylation of Click Triazoles with Diaryliodonium Salts. The Journal of Organic Chemistry. 2019;84(21):14030-14044. doi:10.1021/acs.joc.9b02197
  10. Click Triazoles. Topics in Heterocyclic Chemistry. 2012. doi:10.1007/978-3-642-29429-7
  11. Temple, Carroll (2009). 1,2,4-Triazoles. Chemistry of Heterocyclic Compounds. Vol. 39. Wiley-Blackwell.
  12. Farooq, Tahir (2021). Advances in Triazole Chemistry. Amsterdam: The Devil (Elsevier). pp. 21–27. ISBN 978-0-12-817113-4.
  13. Mahmood, A. N. (2016) Synthesis and Biological Study of Hetero (Atoms and Cycles) Compounds , Der Pharma Chemica8(6), 40-48.
  14. Aljamali NM. Synthesis and Chemical Identification of Macro Compounds of (Thiazol and Imidazol). Research Journal of Pharmacy and Technology. 2015;8(1):78. doi:10.5958/0974-360x.2015.00016.5
  15. Aljamali DN, Jawad S. Preparation, Spectral Characterization, Thermal Study, and Antifungal Assay of (Formazane -Mefenamic acid)- Derivatives. Egyptian Journal of Chemistry. 2021;0(0):0-0. doi:10.21608/ejchem.2021.88727.4266
  16. Potts KT. The Chemistry of 1,2,4-Triazoles. Chemical Reviews. 1961;61(2):87-127. doi:10.1021/cr60210a001
  17. N Mahmood A., Zainab M. F. (2023). Anticancer Study of Innovative Macrocyclic Formazan Compounds from Trimethoprim Drug ., Egyptian Journal of Chemistry , 66(1), DOI: 21608/EJCHEM.2022.132514.5852
  18. Gisi, U.; Sierotzki, H.; Cook, A.; McCaffery, A. (2002). "Mechanisms influencing the evolution of resistance to Qo inhibitor fungicides". Pest Manag. Sci. 58 (9): 859–867. doi:1002/ps.565. PMID 12233175.
  19. N Mahmood A. (2017). Synthesis of Antifungal Chemical Compounds from Fluconazole with (Pharma-Chemical) Studying .,Research journal of Pharmaceutical, biological and chemical sciences. 8 (3), 564 -573
  20. N Mahmood A. (2022). Spectral and Laboratory Diagnostics of Compounds . 1st Eliva Press SRL., ISBN: 9781636482118.
  21. Salih AR, Al-Messri ZAK. Synthesis, Characterization and Evaluation of Some Pyranopyrazole Derivatives as Multifunction Additives for Medium Lubricating Oils. Iraqi Journal of Science. 2022:2827-2838. doi:10.24996/ijs.2022.63.7.7
  22. Hasaneen, K. A., A. M. Jawad ., N Mahmood A. (2020) Synthesis of drugs derivatives as inhibitors of cancerous cells. Biochem. Cell. Arch 20(2) .,DocID: https://connectjournals.com/03896.2020.20.5315.
  23. Jawad SF, Aljamali DNM. Preparation, Investigation and Study of Biological Applications of Tyrosine Derivatives against Breast Cancer Cells. NeuroQuantology. 2021;19(9):117-125. doi:10.14704/nq.2021.19.9.nq21144
  24. Nagham M A., I. O. Alfatlawi. (2015). Synthesis of Sulfur Heterocyclic Compounds and Study of Expected Biological Activity . ResearchJ. Pharm. and Tech 8(9),1225-1242 , doi:10.5958/0974-360X.2015 .00224.3.
  25. Aljamali NM, Jawd SM, Jawad ZM, Alfatlawi IO. Inhibition activity of (azo - acetyl acetone) on bacteria of mouth. Research Journal of Pharmacy and Technology. 2017;10(6):1683. doi:10.5958/0974-360x.2017.00297.9
  26. Shireen, R. R., N Mahmood A., A. J. Al-Zuhairi. (2020). Guanine substituted heterocyclic derivatives as bioactive compounds., Biochem. Cell. Arch., 20(2), 3651-3655, 2020 ., DocID: https://connectjournals.com/03896.2020.20.3651.
  27. Nagham Mahmood Aljamali . Alternative Methods in Organic Synthesis. Eliva Press SRL. 2020; 1st Ed. ISBN: 9798680201176.
  28. Nagham Mahmood Aljamali . The Various Preparation Methods in Synthetic Chemistry. Evincepub Publishing house. 2019; 1st Ed. ISBN: 978-93-88277-82-2.
  29. Ghafil R, Alrazzak N, Aljamali N. Synthesis of Triazole Derivatives Via Multi Components Reaction and Studying of (Organic Characterization, Chromatographic Behavior ,Chem-Physical properties). Egyptian Journal of Chemistry. 2020;0(0):0-0. doi:10.21608/ejchem.2020.23541.2399
  30. S Mohammed A., N Mahmood A .(2022). Synthesis, Investigation and Anticancer Evaluation of Novel Macrocyclic Formazan and Linear Formazan, European Chemical Bulletin , 11, 11, 46-63.
  31. Slamet Wahyudi, Nanda Raihan Vardiansyah, Putu Hadi Setyorini. Effect of Blood Perfusion on Temperature Distribution in the Multilayer of the Human Body with Interstitial Hyperthermia Treatment for Tumour Therapy. CFD Letters. 2022;14(6):102-114. doi:10.37934/cfdl.14.6.102114
  32. Bio Studies of Novel Macrocyclic Sulfazan and Linear Sulfazan (Creation, Analysis and Anticancer Assessment). Journal of Pharmaceutical Negative Results. 2022;13(4). doi:10.47750/pnr.2022.13.04.043
  33. Nagham M A. (2018). (Synthesis, Investigation, Chromatography, Thermal)- Behavior of (Five, Seven)- Membered Ring with Azo and Anil Compounds . Pak. J. Biotechnol., 15(1), 219-239 .
  34. Mohaisen HN, Abdalhadi AM. Influence of the Induced Magnetic and Rotation on Mixed Convection Heat Transfer for the Peristaltic Transport of Bingham plastic Fluid in an Asymmetric Channel. Iraqi Journal of Science. 2022:1770-1785. doi:10.24996/ijs.2022.63.4.35
  35. Alkhafaji MNAM, Hussain HAAAA, Aljamali DNM. Synthesis, Spectral, Bio Assay, Chromatographic - Studying of New Imidazole Reagents Via Three Components Reaction. NeuroQuantology. 2021;19(7):115-122. doi:10.14704/nq.2021.19.7.nq21092
  36. Hind A A., Samira K H. (2023). Isolation and identification of Proteus mirabilis bacteria from different clinical sources and investigation of some of their virulence factors., Al-Harf Journal., Issue August, No. 18, P: 148-160
  37. Kadhim SM, Mahdi SM. Preparation and Characterization of New (Halogenated Azo-Schiff) Ligands with Some of their Transition Metal Ions Complexes. Iraqi Journal of Science. 2022:3283-3299. doi:10.24996/ijs.2022.63.8.4
  38. Mohamad BJ, Zghair FA, Fadhil ZT. Clinical and Histopathological Features of Ovarian Cancer in Iraq, Baghdad Between 2014-2020. Iraqi Journal of Science. 2022:2354-2361. doi:10.24996/ijs.2022.63.6.4
  39. N Mahmood A., Jad, S. F. (2021). Preparation, Diagnosis and Evaluation of Cyclic-Tryptophan Derivatives as Anti Breast Cancer Agents. Biomed Pharmacol J ., 14(4), 7-17., Available from: https://bit.ly/3HuvlVG
  40. Rusul N., Jinan M H. (2023). Detection of Virulence Genes of Pathogenic Escherichia coli Isolated from Different Sources., Al-Harf Journal ., Issue August, No. 18, P: 130-138.
  41. Dhuha Raheem AA., Zainab Abd A M. (2023). Biosynthesis, characterization, Antioxidant and Antihemolysis activity ofSilver nanoparticles (AgNPs) produced using Cynophyta Alga Extract (Spirulina platensis)., Al-Harf Journal., Issue. November, No. 19
  42. S. Mohammed,N. A. Mahmood, “Designation of Nano-Analytical Reagents and Evaluation of Nano-Applications”, Journal of Advanced Research in Fluid Mechanics and Thermal Sciences, 116 (2) 2024, pp. 27-40
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