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Research Article

Synthesis and anticancer activity evaluation of some novel imidazo[1,2-a]pyridine based heterocycles containing S-alkyl/aryl moiety

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Received 21 Aug 2023, Accepted 20 Apr 2024, Published online: 22 May 2024

References

  • Jordan, A.; Hadfield, J. A.; Lawrence, N. J.; McGown, A. T. Tubulin as a Target for Anticancer Drugs: Agents Which İnteract with the Mitotic Spindle. Med. Res. Rev. 1998, 18, 259–296. DOI: 10.1002/(SICI)1098-1128(199807)18:4.
  • Goel, R.; Luxami, V.; Paul, K. Imidazo[1,2-a]Pyridines: Promising Drug Candidate for Antitumor Therapy. Curr. Top. Med. Chem. 2016, 16, 3590–3616. DOI: 10.2174/1568026616666160414122644.
  • Dahan-Farkas, N.; Langley, C.; Rousseau, A. L.; Yadav, D. B.; Davids, H.; de Koning, C. B. 6-Substituted İmidazo[1,2-a]Pyridines: Synthesis and Biological Activity against Colon Cancer Cell Lines HT-29 and Caco-2. Eur. J. Med. Chem. 2011, 46, 4573–4583. DOI: 10.1016/j.ejmech.2011.07.036.
  • Claiborne, C.; Liverton, N.; Nguyen, K. An Efficient Synthesis of Tetrasubstituted İmidazoles from N-(2-Oxo)-Amides. Tetrahedron Lett. 1998, 39, 8939–8942. DOI: 10.1016/s0040-4039(98)02058-9.
  • de Vita, D.; Scipione, L.; Tortorella, S.; Mellini, P.; Di Rienzo, B.; Simonetti, G.; D'Auria, F. D.; Panella, S.; Cirilli, R.; Di Santo, R.; Palamara, A. T. Synthesis and Antifungal Activity of a New Series of 2-(1Himidazol-1-Yl)-1-Phenylethanol Derivatives. Eur. J. Med. Chem. 2012, 49, 334–342. DOI: 10.1016/j.ejmech.2012.01.034.
  • Iradyan, M. A.; Iradyan, N. S.; Arsenyan, F. G.; Stepanyan, G. M. Imidazole Derivatives and Their Antitumor Activity (Review). Pharm. Chem. J. 2009, 43, 439–443. DOI: 10.1007/s11094-009-0333-9.
  • Cui, B.; Zheng, B. L.; He, K.; Zheng, Q. Y. Imidazole Alkaloids from Lepidium Meyenii. J. Nat. Prod. 2003, 66, 1101–1103. DOI: 10.1021/np030031i.
  • Mlostoń, G.; Kowalczyk, M.; Celeda, M.; Gach-Janczak, K.; Janecka, A.; Jasiński, M. Synthesis and Cytotoxic Activity of Lepidilines A–D: Comparison with Some 4, 5-Diphenyl Analogues and Related İmidazole-2-Thiones. J. Nat. Prod. 2021, 84, 3071–3079. DOI: 10.1021/acs.jnatprod.1c00797.
  • Bedadurge, A. B.; Shaikh, A. R. Designing Hypothesis of 2-Substituted-N-[4-(1-Methyl-4,5-Diphenyl-1H-İmidazole-2-Yl)Phenyl] Acetamide Analogs as Anticancer Agents: QSAR Approach. J. Korean Chem. Soc. 2013, 57, 744–754. DOI: 10.5012/jkcs.2013.57.6.744.
  • Sayeed, I. B.; Lakshma Nayak, V.; Shareef, M. A.; Chouhan, N. K.; Kamal, A. Design, Synthesis and Biological Evaluation of İmidazopyridine–Propenone Conjugates as Potent Tubulin İnhibitors. Medchemcomm. 2017, 8, 1000–1006. DOI: 10.1039/c7md00043j.
  • Vellakkaran, M.; Lingayya, R.; Naveen Kumar, B.; Nagaiah, K.; Poornachandra, Y.; Ganesh Kumar, C. Palladium(0)-Catalyzed Direct C–H Heteroarylation of 2-Arylimidazo [1,2-a]Pyridines with (E)-1-(5-Bromothiophen-2-Yl)-3-Arylprop-2-En-1-Ones and Their Anticancer Activity. RSC Adv. 2015, 5, 80057–80062. DOI: 10.1039/C5RA15078G.
  • Gayatri Devi, B.; Saisree, K.; Sikender, M.; Madhava Reddy, B.; Harinadha Babu, V. Synthesis and Biological Evaluation of 2,4-Thiazolidinedione İncorporated İmidazo[1,2-a]Pyridines. Der Pharma Chem. 2016, 8, 180–184.
  • Jin, Y.; Rho, M. C.; Gajulapati, K.; Jung, H. Y. Synthesis of a Novel Series of İmidazo[1,2-α]Pyridines as acyl-CoA: Cholesterol Acyltransferase (ACAT) İnhibitors. Bull. Korean Chem. Soc. 2009, 30, 1297–1304. DOI: 10.5012/bkcs.2009.30.6.1297.
  • El-Sayed, W. M.; Hussin, W. A.; Al-Faiyz, Y. S.; Ismail, M. A. The Position of İmidazopyridine and Metabolic Activation Are Pivotal Factors in the Antimutagenic Activity of Novel İmidazo[1,2-a]Pyridine Derivatives. Eur. J. Pharmacol. 2013, 715, 212–218. DOI: 10.1016/j.ejphar.2013.05.018.
  • Sanghai, N.; Jain, V.; Preet, R.; Kandekar, S.; Das, S.; Trivedi, N.; Mohapatra, P.; Priyadarshani, G.; Kashyap, M.; Das, D.; et al. Combretastatin A-4 İnspired Novel 2-Aryl-3-Arylamino-İmidazo-Pyridines/Pyrazines as Tubulin Polymerization İnhibitors, Antimitotic and Anticancer Agents. Med. Chem. Comm. 2014, 5, 766–782. DOI: 10.1039/C3MD00357D.
  • Kamal, A.; Bharath Kumar, G.; Lakshma Nayak, V.; Reddy, V. S.; Shaik, A. B.; Rajender, R.; Kashi Reddy, M. Design, Synthesis and Biological Evaluation of İmidazopyridine/İmidazopyrimidine-Benzimidazole Conjugates as Potential Anticancer Agents. Med. Chem. Commun. 2015, 6, 606–612. DOI: 10.1039/C4MD00400K.
  • Kishbaugh, T. L. S. Pyridines and İmidazopyridines with Medicinal Significance. Curr. Top. Med. Chem. 2016, 16, 3274–3302. DOI: 10.2174/1568026616666160506145141.
  • Andaloussi, M.; Moreau, E.; Masurier, N.; Lacroix, J.; Gaudreault, R. C.; Chezal, J. M.; El Laghdach, A.; Canitrot, D.; Debiton, E.; Teulade, J. C.; Chavignon, O. Novel İmidazo[1,2-a]Naphthyridinic Systems (Part 1): Synthesis, Antiproliferative and DNA-İntercalating Activities. Eur. J. Med. Chem. 2008, 43, 2505–2517. DOI: 10.1016/j.ejmech.2008.02.017.
  • Hayakawa, M.; Kaizawa, H.; Kawaguchi, K.-I.; Ishikawa, N.; Koizumi, T.; Ohishi, T.; Yamano, M.; Okada, M.; Ohta, M.; Tsukamoto, S.-I.; et al. Synthesis and Biological Evaluation of İmidazo[1,2-a]Pyridine Derivatives as Novel PI3 Kinase p110a İnhibitors. Bioorg. Med. Chem. 2007, 15, 403–412. DOI: 10.1016/j.bmc.2006.09.047.
  • Cosimelli, B.; Laneri, S.; Ostacolo, C.; Sacchi, A.; Severi, E.; Porcù, E.; Rampazzo, E.; Moro, E.; Basso, G.; Viola, G. Synthesis and Biological Evaluation of İmidazo[1,2-a]Pyrimidines and İmidazo[1,2-a]Pyridines as New İnhibitors of the Wnt/b-Catenin Signaling. Eur. J. Med. Chem. 2014, 83, 45–56. DOI: 10.1016/j.ejmech.2014.05.071.
  • Byth, K. F.; Culshaw, J. D.; Green, S.; Oakes, S. E.; Thomas, A. P. Imidazo[1,2-a]Pyridines. Part 2: SAR and Optimisation of a Potent and Selective Class of Cyclin-Dependent Kinase İnhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 2245–2248. DOI: 10.1016/j.bmcl.2004.02.015.
  • Xu, Y.; Wang, N. Y.; Song, X. J.; Lei, Q.; Ye, T. H.; You, X. Y.; Zuo, W. Q.; Xia, Y.; Zhang, L. D.; Yu, L. T. Discovery of Novel N-(5-(Tert-Butyl)İsoxazol-3-Yl)-N’-Phenylurea Analogs as Potent FLT3 İnhibitors and Evaluation of Their Activity against Acute Myeloid Leukemia In vitro and In vivo. Bioorg. Med. Chem. 2015, 23, 4333–4343. DOI: 10.1016/j.bmc.2015.06.033.
  • Lee, H.; Kim, S. J.; Jung, K. H.; Son, M. K.; Yan, H. H.; Hong, S.; Hong, S.-S. A Novel İmidazopyridine PI3K İnhibitor with Anticancer Activity in Non-Small Cell Lung Cancer Cells. Oncol. Rep. 2013, 30, 863–869. DOI: 10.3892/or.2013.2499.
  • Hamdouchi, C.; Zhong, B.; Mendoza, J.; Collins, E.; Jaramillo, C.; De Diego, J. E.; Robertson, D.; Spencer, C. D.; Anderson, B. D.; Watkins, S. A.; et al. Structure-Based Design of a New Class of Highly Selective Aminoimidazo[1,2-a]Pyridine-Based İnhibitors of Cyclin Dependent Kinases. Bioorg. Med. Chem. Lett. 2005, 15, 1943–1947. DOI: 10.1016/j.bmcl.2005.01.052.
  • Temple, C.; Jr., Rose, J. D.; Comber, R. N.; Rener, G. A. Synthesis of Potential Anticancer Agents: İmidazo[4,5-c]Pyridines and İmidazo[4,5-b]Pyridines. J. Med. Chem. 1987, 30, 1746–1751. DOI: 10.1021/jm00393a011.
  • Anderson, M.; Beattie, J. F.; Breault, G. A.; Breed, J.; Byth, K. F.; Culshaw, J. D.; Ellston, R. P.; Green, S.; Minshull, C. A.; Norman, R. A.; et al. Imidazo[1,2-a]Pyridines: A Potent and Selective Class of Cyclin-Dependent Kinase İnhibitors İdentified through Structure-Based Hybridization. Bioorg. Med. Chem. Lett. 2003, 13, 3021–3026. DOI: 10.1016/S0960-894X(03)00638-3.
  • Masurier, N.; Debiton, E.; Jacquemet, A.; Bussière, A.; Chezal, J. M.; Ollivier, A.; Tétégan, D.; Andaloussi, M.; Galmier, M. J.; Lacroix, J.; et al. Imidazonaphthyridine Systems (Part 2): Functionalization of the Phenyl Ring Linked to the Pyridine Pharmacophore and İts Replacement by a Pyridinone Ring Produces İntriguing Differences in Cytocidal Activity. Eur. J. Med. Chem. 2012, 52, 137–150. DOI: 10.1016/j.ejmech.2012.03.011.
  • Lawson, M.; Rodrigo, J.; Baratte, B.; Robert, T.; Delehouzé, C.; Lozach, O.; Ruchaud, S.; Bach, S.; Brion, J. D.; Alami, M.; Hamze, A. Synthesis, Biological Evaluation and Molecular Modeling Studies of İmidazo[1,2-a]Pyridines Derivatives as Protein Kinase İnhibitors. Eur. J. Med. Chem. 2016, 123, 105–114. DOI: 10.1016/j.ejmech.2016.07.040.
  • Cai, D.; Byth, K. F.; Shapiro, G. I. AZ703, an İmidazo[1,2-a]Pyridine İnhibitor of Cyclin-Dependent Kinases 1 and 2, İnduces E2F-1-Dependent Apoptosis Enhanced by Depletion of Cyclin-Dependent Kinase 9. Cancer Res. 2006, 66, 435–444. DOI: 10.1158/0008-5472.CAN-05-1769.
  • Byth, K. F.; Geh, C.; Forder, C. L.; Oakes, S. E.; Thomas, A. P. The Cellular Phenotype of AZ703, a Novel Selective İmidazo[1,2-a]Pyridine Cyclin-Dependent Kinase İnhibitor. Mol. Cancer Ther. 2006, 5, 655–664. DOI: 10.1158/1535-7163.MCT-05-0205.
  • Rassokhina, I. V.; Volkova, Y. A.; Kozlov, A. S.; Scherbakov, A. M.; Andreeva, O. E.; Shirinian, V. Z.; Zavarzin, I. V. Synthesis and Antiproliferative Activity Evaluation of Steroidal İmidazo [1,2-a]Pyridines. Steroids 2016, 113, 29–37. DOI: 10.1016/j.steroids.2016.06.001.
  • Sundberg, R. J.; Dahlhausen, D. J.; Manikumar, G.; Mavunkel, B.; Biswas, A.; Srinivasan, V.; King, F.; Jr., Waid, P. Preparation of 2‐Aryl and 2‐Aryloxymethyl İmidazo [1, 2‐a]Pyridines and Related Compounds. J. Heterocyclic Chem. 1988, 25, 129–137. DOI: 10.1002/jhet.5570250119.
  • Iradyan, M. A.; Iradyan, N. S.; Paronikyan, R. V.; Stepanyan, G. M. Synthesis and Biological Activity of 2-Phenylimidazo[1,2-a]Pyridine Derivatives. Hayastani Kimiakan Handes 2008, 61, 273–279.
  • do Amaral, D. N.; Cavalcanti, B. C.; Bezerra, D. P.; Ferreira, P. M.; Castro, R.; de, P.; Sabino, J. R.; Machado, C. M.; Chammas, R.; Pessoa, C.; et al. Docking, Synthesis and Antiproliferative Activity of N-Acylhydrazone Derivatives Designed as Combretastatin A4 Analogues. PLoS One. 2014, 9, e85380. DOI: 10.1371/journal.pone.0085380.
  • Antoszczak, M.; Popiel, K.; Stefańska, J.; Wietrzyk, J.; Maj, E.; Janczak, J.; Michalska, G.; Brzezinski, B.; Huczyński, A. Synthesis, Cytotoxicity and Antibacterial Activity of New Esters of Polyether Antibiotic-Salinomycin. Eur. J. Med. Chem. 2014, 76, 435–444. DOI: 10.1016/j.ejmech.2014.02.031.
  • Chelopo, M. P.; Pawar, S. A.; Sokhela, M. K.; Govender, T.; Kruger, H. G.; Maguire, G. E. Anticancer Activity of Ruthenium(II) Arene Complexes Bearing 1,2,3,4-Tetrahydroisoquinoline Amino Alcohol Ligands. Eur. J. Med. Chem. 2013, 66, 407–414. DOI: 10.1016/j.ejmech.2013.05.048.
  • Fulda, S.; Debatin, K. M. Caspase Activation in Cancer Therapy. In Madame Curie Bioscience Database [Internet]. Landes Biosci. 2013, 1–19.
  • Van Opdenbosch, N.; Lamkanfi, M. Caspases in Cell Death, İnflammation, and Disease. Immunity 2019, 50, 1352–1364. DOI: 10.1016/j.immuni.2019.05.020.
  • McIlwain, D. R.; Berger, T.; Mak, T. W. Caspase Functions in Cell Death and Disease. Cold Spring Harb. Perspect. Biol. 2013, 5, a008656–a008656. DOI: 10.1101/cshperspect.a026716.
  • Acar Çevik, U.; Osmaniye, D.; Sağlik, B. N.; Levent, S.; K. Çavuşoğlu, B.; Karaduman, A. B.; D. Özkay, Ü.; Özkay, Y.; Kaplancikli, Z. A.; Turan, G. Synthesis of New Benzothiazole Derivatives Bearing Thiadiazole as Monoamine Oxidase İnhibitors. Journal of Heterocyclic Chem. 2020, 57, 2225–2233. DOI: 10.1002/jhet.3942.
  • Kaya, B.; Hussin, W.; Yurttaş, L.; Turan-Zitouni, G.; Gençer, H. K.; Baysal, M.; Karaduman, A. B.; Kaplancıklı, Z. A. Design and Synthesis of New 1,3,4-Oxadiazole - Benzothiazole and Hydrazone Derivatives as Promising Chemotherapeutic Agents. Drug Res. (Stuttg) 2017, 67, 275–282. DOI: 10.1055/s-0042-119070.
  • Yurttaş, L.; Demirayak, S.; Ilgın, S.; Atlı, Ö. In Vitro Antitumor Activity Evaluation of Some 1,2,4-Triazine Derivatives Bearing Piperazine Amide Moiety against Breast Cancer Cells. Bioorg. Med. Chem. 2014, 22, 6313–6323. DOI: 10.1016/j.bmc.2014.10.002.
  • Kisa, D.; Koç, E.; Sena, K.; Topcu, B.; İmamoğlu, R. Heterocyclic Compounds with Different Moieties: Synthesis and Evaluation of Biological Activities Assisted with the Computational Study. J. Biomol. Struct. Dyn. 2023, 1–10. DOI: 10.1080/07391102.2023.2268182.
  • Oleg, T.; Olson, A. J. AutoDock Vina: Improving the Speed and Accuracy of Docking with a New Scoring Function, Efficient Optimization, and Multithreading. J. Comput. Chem. 2010, 31, 455–461. DOI: 10.1002/jcc.21334.
  • İmamoğlu, R.; Koç, E.; Kısa, D. Polyphenolic Compounds: Synthesis, Assessment of Antimicrobial Effect and Enzymes İnhibition against İmportant Medicinal Enzymes with Computational Details. Bioorg. Med. Chem. Lett. 2022, 65, 128722. DOI: 10.1016/j.bmcl.2022.128722.
  • Kaya, Z.; İmamoğlu, R.; Ceylan, K. B.; Genç, N.; Kısa, D. Evaluation of Metabolic Enzyme İnhibitory Potency with Molecular Docking Assisted Studies: Phenolic Compound Analysis of Seseli Resinosum. J. Biol. Act. Prod. Nat. 2023, 13, 49–67. DOI: 10.1080/22311866.2023.2186488.

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