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Novel 4-thiazolidinone derivatives bearing imidazo[2,1- b]thiazole moiety: design, synthesis, and antiviral activity evaluation

Yıl 2023, Cilt: 27 Sayı: 2, 924 - 935, 27.06.2025

Faika Başoğlu-ünal Selin Cimok Efe Doğukan Dincel , Lieve Naesens Nuray Ulusoy Güzeldemirci

Öz

This paper aimed to synthesize novel compounds carrying imidazo[2,1-b]thiazole nucleus, characterize
them with various spectroscopic methods, moreover evaluate their antiviral activity. All novel derivatives were
evaluated for their antiviral activity against Coxsackie B4 virus, Respiratory syncytial virus, Influenza A/H1N1 virus,
Influenza A/H3N2, and Influenza B virus. Some of the compounds, particularly the derivatives carrying 4-
methylphenyl and 4-bromophenyl moiety, exhibited higher and comparable activities against both Coxsackie B4 and
Respiratory syncytial viruses, moreover the compounds with N-propyl and N-butyl at thiazolidinone ring showed high
antiviral activities against Influenza Influenza A/H3N2 viruses. Consequently, the results obtained from in vitro assay
data shed light on improving novel antiviral.

Anahtar Kelimeler

Imidazo[2 1-b]thiazole 4-thiazolidinone antiviral activity coxscakie b4 virus influenza

Kaynakça

  • K.F. Atta, O.O. Farahat, A.Z. Ahmed, M.G. Marei, Synthesis and antibacterial activities of novel imidazo[2,1-b]-1,3,4-thiadiazoles, Molecules 16(7) (2011) 5496-506. https://doi.org/10.3390/molecules16075496.
  • N.U. Guzeldemirci, O. Kucukbasmaci, Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety, Eur J Med Chem 45(1) (2010) 63-8. https://doi.org/10.1016/j.ejmech.2009.09.024.
  • N. Ulusoy Guzeldemirci, B. Karaman, O. Kucukbasmaci, Antibacterial, Antitubercular and Antiviral Activity Evaluations of Some Arylidenehydrazide Derivatives Bearing Imidazo[2,1- b]thiazole Moiety, Turk J Pharm Sci 14(2) (2017) 157-163. https://doi.org/10.4274/tjps.25743.
  • F. Basoglu, N. Ulusoy-Guzeldemirci, G. Akalin-Ciftci, S. Cetinkaya, A. Ece, Novel imidazo[2,1- b]thiazole-based anticancer agents as potential focal adhesion kinase inhibitors: synthesis, in silico, and in vitro evaluation, Chem Biol Drug Des (2021). https://doi.org/10.1111/cbdd.13896.
  • A.R. Ali, E.R. El-Bendary, M.A. Ghaly, I.A. Shehata, Synthesis, in vitro anticancer evaluation and in silico studies of novel imidazo[2,1-b]thiazole derivatives bearing pyrazole moieties, Eur J Med Chem 75 (2014) 492-500. https://doi.org/10.1016/j.ejmech.2013.12.010.
  • N.Y. Wang, Y. Xu, W.Q. Zuo, K.J. Xiao, L. Liu, X.X. Zeng, X.Y. You, L.D. Zhang, C. Gao, Z.H. Liu, T.H. Ye, Y. Xia, Y. Xiong, X.J. Song, Q. Lei, C.T. Peng, H. Tang, S.Y. Yang, Y.Q. Wei, L.T. Yu, Discovery of imidazo[2,1-b]thiazole HCV NS4B inhibitors exhibiting synergistic effect with other direct-acting antiviral agents, J Med Chem 58(6) (2015) 2764-78. https://doi.org/10.1021/jm501934n.
  • A. Andreani, M. Rambaldi, A. Locatelli, R. Bossa, I. Galatulas, G. Salvatore, Antitumor and cardiotonic activity of imidazo[2,1-b]thiazole guanylhydrazones, In Vivo 8(6) (1994) 1031-2.
  • N. Scheinfeld, J.D. Rosenberg, J.M. Weinberg, Levamisole in dermatology : a review, Am J Clin Dermatol 5(2) (2004) 97-104. https://doi.org/10.2165/00128071-200405020-00004.
  • Drugs@FDA: FDA-Approved Drugs. https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo =020035.
  • A. Petrou, M. Fesatidou, A. Geronikaki, Thiazole Ring-A Biologically Active Scaffold, Molecules 26(11) (2021). https://doi.org/10.3390/molecules26113166.
  • K.A. Szychowski, B. Skora, A. Kryshchyshyn-Dylevych, D. Kaminskyy, K. Rybczynska- Tkaczyk, R. Lesyk, J. Gminski, Induction of Cyp450 enzymes by 4-thiazolidinone-based derivatives in 3T3-L1 cells in vitro, Naunyn Schmiedebergs Arch Pharmacol 394(5) (2021) 915-927. https://doi.org/10.1007/s00210-020-02025-7.
  • R. Tahmasvand, P. Bayat, S.M. Vahdaniparast, S. Dehghani, Z. Kooshafar, S. Khaleghi, A. Almasirad, M. Salimi, Design and synthesis of novel 4-thiazolidinone derivatives with promising anti-breast cancer activity: Synthesis, characterization, in vitro and in vivo results, Bioorg Chem 104 (2020) 104276. https://doi.org/10.1016/j.bioorg.2020.104276.
  • K. Szabo, R. Maccari, R. Ottana, G. Gyemant, Extending the investigation of 4-thiazolidinone derivatives as potential multi-target ligands of enzymes involved in diabetes mellitus and its long- term complications: A study with pancreatic alpha-amylase, Carbohydr Res 499 (2021) 108220. https://doi.org/10.1016/j.carres.2020.108220.
  • N.U. Güzeldemirci, Pehlivan, E., Naesens, L., Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo [2,1-b] thiazole moiety, Marmara Pharm. J 22(2) (2018) 237-248.
  • G. Cihan-Ustundag, E. Gursoy, L. Naesens, N. Ulusoy-Guzeldemirci, G. Capan, Synthesis and antiviral properties of novel indole-based thiosemicarbazides and 4-thiazolidinones, Bioorg Med Chem 24(2) (2016) 240-6. https://doi.org/10.1016/j.bmc.2015.12.008.
  • N. Ulusoy Güzeldemirci, E. Pehlivan, L. Naesens, Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety, Marmara Pharmaceutical Journal 22 (2017) 237-348.
  • A. Chotera-Ouda, A. Wróblewska, P. Tokarz, C.V. Stevens, Thiazoles, in: D. Black, J. Cossy, C. Stevens (Eds.), Journal: Comprehensive Heterocyclic Chemistry IV2022, pp. 530-623.
  • F. Basoglu, N. Ulusoy-Guzeldemirci, G. Akalin-Ciftci, S. Cetinkaya, A. Ece, Novel imidazo[2,1- b]thiazole-based anticancer agents as potential focal adhesion kinase inhibitors: Synthesis, in silico and in vitro evaluation, Chem Biol Drug Des 98(2) (2021) 270-282. https://doi.org/10.1111/cbdd.13896.
  • A. Deep, P. Kumar, B. Narasimhan, K. Ramasamy, V. Mani, R.K. Mishra, A.B. Majeed, Synthesis, antimicrobial, anticancer evaluation of 2-(aryl)-4- thiazolidinone derivatives and their QSAR studies, Curr Top Med Chem 15(11) (2015) 990-1002. https://doi.org/10.2174/1568026615666150317221849.
  • N. Ulusoy Guzeldemirci, S. Cimok, N. Das-Evcimen, M. Sarikaya, Synthesis and Aldose Reductase Inhibitory Effect of Some New Hydrazinecarbothioamides and 4-Thiazolidinones Bearing an Imidazo[2,1-b]Thiazole Moiety, Turk J Pharm Sci 16(1) (2019) 1-7. https://doi.org/10.4274/tjps.05900.
  • S. Holota, A. Kryshchyshyn, H. Derkach, Y. Trufin, I. Demchuk, A. Gzella, P. Grellier, R. Lesyk, Synthesis of 5-enamine-4-thiazolidinone derivatives with trypanocidal and anticancer activity, Bioorg Chem 86 (2019) 126-136. https://doi.org/10.1016/j.bioorg.2019.01.045.
  • Significant Research Advances Enabled by HeLa Cells. https://osp.od.nih.gov/scientific- sharing/hela-cells-timeline/. 2022).
  • E. Vanderlinden, F. Goktas, Z. Cesur, M. Froeyen, M.L. Reed, C.J. Russell, N. Cesur, L. Naesens, Novel inhibitors of influenza virus fusion: structure-activity relationship and interaction with the viral hemagglutinin, J Virol 84(9) (2010) 4277-88. https://doi.org/10.1128/JVI.02325-09.

Yıl 2023, Cilt: 27 Sayı: 2, 924 - 935, 27.06.2025

Faika Başoğlu-ünal Selin Cimok Efe Doğukan Dincel , Lieve Naesens Nuray Ulusoy Güzeldemirci

Öz

Kaynakça

  • K.F. Atta, O.O. Farahat, A.Z. Ahmed, M.G. Marei, Synthesis and antibacterial activities of novel imidazo[2,1-b]-1,3,4-thiadiazoles, Molecules 16(7) (2011) 5496-506. https://doi.org/10.3390/molecules16075496.
  • N.U. Guzeldemirci, O. Kucukbasmaci, Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety, Eur J Med Chem 45(1) (2010) 63-8. https://doi.org/10.1016/j.ejmech.2009.09.024.
  • N. Ulusoy Guzeldemirci, B. Karaman, O. Kucukbasmaci, Antibacterial, Antitubercular and Antiviral Activity Evaluations of Some Arylidenehydrazide Derivatives Bearing Imidazo[2,1- b]thiazole Moiety, Turk J Pharm Sci 14(2) (2017) 157-163. https://doi.org/10.4274/tjps.25743.
  • F. Basoglu, N. Ulusoy-Guzeldemirci, G. Akalin-Ciftci, S. Cetinkaya, A. Ece, Novel imidazo[2,1- b]thiazole-based anticancer agents as potential focal adhesion kinase inhibitors: synthesis, in silico, and in vitro evaluation, Chem Biol Drug Des (2021). https://doi.org/10.1111/cbdd.13896.
  • A.R. Ali, E.R. El-Bendary, M.A. Ghaly, I.A. Shehata, Synthesis, in vitro anticancer evaluation and in silico studies of novel imidazo[2,1-b]thiazole derivatives bearing pyrazole moieties, Eur J Med Chem 75 (2014) 492-500. https://doi.org/10.1016/j.ejmech.2013.12.010.
  • N.Y. Wang, Y. Xu, W.Q. Zuo, K.J. Xiao, L. Liu, X.X. Zeng, X.Y. You, L.D. Zhang, C. Gao, Z.H. Liu, T.H. Ye, Y. Xia, Y. Xiong, X.J. Song, Q. Lei, C.T. Peng, H. Tang, S.Y. Yang, Y.Q. Wei, L.T. Yu, Discovery of imidazo[2,1-b]thiazole HCV NS4B inhibitors exhibiting synergistic effect with other direct-acting antiviral agents, J Med Chem 58(6) (2015) 2764-78. https://doi.org/10.1021/jm501934n.
  • A. Andreani, M. Rambaldi, A. Locatelli, R. Bossa, I. Galatulas, G. Salvatore, Antitumor and cardiotonic activity of imidazo[2,1-b]thiazole guanylhydrazones, In Vivo 8(6) (1994) 1031-2.
  • N. Scheinfeld, J.D. Rosenberg, J.M. Weinberg, Levamisole in dermatology : a review, Am J Clin Dermatol 5(2) (2004) 97-104. https://doi.org/10.2165/00128071-200405020-00004.
  • Drugs@FDA: FDA-Approved Drugs. https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo =020035.
  • A. Petrou, M. Fesatidou, A. Geronikaki, Thiazole Ring-A Biologically Active Scaffold, Molecules 26(11) (2021). https://doi.org/10.3390/molecules26113166.
  • K.A. Szychowski, B. Skora, A. Kryshchyshyn-Dylevych, D. Kaminskyy, K. Rybczynska- Tkaczyk, R. Lesyk, J. Gminski, Induction of Cyp450 enzymes by 4-thiazolidinone-based derivatives in 3T3-L1 cells in vitro, Naunyn Schmiedebergs Arch Pharmacol 394(5) (2021) 915-927. https://doi.org/10.1007/s00210-020-02025-7.
  • R. Tahmasvand, P. Bayat, S.M. Vahdaniparast, S. Dehghani, Z. Kooshafar, S. Khaleghi, A. Almasirad, M. Salimi, Design and synthesis of novel 4-thiazolidinone derivatives with promising anti-breast cancer activity: Synthesis, characterization, in vitro and in vivo results, Bioorg Chem 104 (2020) 104276. https://doi.org/10.1016/j.bioorg.2020.104276.
  • K. Szabo, R. Maccari, R. Ottana, G. Gyemant, Extending the investigation of 4-thiazolidinone derivatives as potential multi-target ligands of enzymes involved in diabetes mellitus and its long- term complications: A study with pancreatic alpha-amylase, Carbohydr Res 499 (2021) 108220. https://doi.org/10.1016/j.carres.2020.108220.
  • N.U. Güzeldemirci, Pehlivan, E., Naesens, L., Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo [2,1-b] thiazole moiety, Marmara Pharm. J 22(2) (2018) 237-248.
  • G. Cihan-Ustundag, E. Gursoy, L. Naesens, N. Ulusoy-Guzeldemirci, G. Capan, Synthesis and antiviral properties of novel indole-based thiosemicarbazides and 4-thiazolidinones, Bioorg Med Chem 24(2) (2016) 240-6. https://doi.org/10.1016/j.bmc.2015.12.008.
  • N. Ulusoy Güzeldemirci, E. Pehlivan, L. Naesens, Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety, Marmara Pharmaceutical Journal 22 (2017) 237-348.
  • A. Chotera-Ouda, A. Wróblewska, P. Tokarz, C.V. Stevens, Thiazoles, in: D. Black, J. Cossy, C. Stevens (Eds.), Journal: Comprehensive Heterocyclic Chemistry IV2022, pp. 530-623.
  • F. Basoglu, N. Ulusoy-Guzeldemirci, G. Akalin-Ciftci, S. Cetinkaya, A. Ece, Novel imidazo[2,1- b]thiazole-based anticancer agents as potential focal adhesion kinase inhibitors: Synthesis, in silico and in vitro evaluation, Chem Biol Drug Des 98(2) (2021) 270-282. https://doi.org/10.1111/cbdd.13896.
  • A. Deep, P. Kumar, B. Narasimhan, K. Ramasamy, V. Mani, R.K. Mishra, A.B. Majeed, Synthesis, antimicrobial, anticancer evaluation of 2-(aryl)-4- thiazolidinone derivatives and their QSAR studies, Curr Top Med Chem 15(11) (2015) 990-1002. https://doi.org/10.2174/1568026615666150317221849.
  • N. Ulusoy Guzeldemirci, S. Cimok, N. Das-Evcimen, M. Sarikaya, Synthesis and Aldose Reductase Inhibitory Effect of Some New Hydrazinecarbothioamides and 4-Thiazolidinones Bearing an Imidazo[2,1-b]Thiazole Moiety, Turk J Pharm Sci 16(1) (2019) 1-7. https://doi.org/10.4274/tjps.05900.
  • S. Holota, A. Kryshchyshyn, H. Derkach, Y. Trufin, I. Demchuk, A. Gzella, P. Grellier, R. Lesyk, Synthesis of 5-enamine-4-thiazolidinone derivatives with trypanocidal and anticancer activity, Bioorg Chem 86 (2019) 126-136. https://doi.org/10.1016/j.bioorg.2019.01.045.
  • Significant Research Advances Enabled by HeLa Cells. https://osp.od.nih.gov/scientific- sharing/hela-cells-timeline/. 2022).
  • E. Vanderlinden, F. Goktas, Z. Cesur, M. Froeyen, M.L. Reed, C.J. Russell, N. Cesur, L. Naesens, Novel inhibitors of influenza virus fusion: structure-activity relationship and interaction with the viral hemagglutinin, J Virol 84(9) (2010) 4277-88. https://doi.org/10.1128/JVI.02325-09.
Toplam 23 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Farmasotik Kimya
Bölüm Articles
Yazarlar

Faika Başoğlu-ünal

Selin Cimok 0000-0002-6021-4065

Efe Doğukan Dincel 0000-0002-5445-0600

Lieve Naesens 0000-0001-9742-9302

Nuray Ulusoy Güzeldemirci 0000-0002-4495-4282

Yayımlanma Tarihi 27 Haziran 2025
Yayımlandığı Sayı Yıl 2023 Cilt: 27 Sayı: 2

Kaynak Göster

APA Başoğlu-ünal, F., Cimok, S., Dincel, E. D., Naesens, L., vd. (2025). Novel 4-thiazolidinone derivatives bearing imidazo[2,1- b]thiazole moiety: design, synthesis, and antiviral activity evaluation. Journal of Research in Pharmacy, 27(2), 924-935.
AMA Başoğlu-ünal F, Cimok S, Dincel ED, Naesens L, Ulusoy Güzeldemirci N. Novel 4-thiazolidinone derivatives bearing imidazo[2,1- b]thiazole moiety: design, synthesis, and antiviral activity evaluation. J. Res. Pharm. Haziran 2025;27(2):924-935.
Chicago Başoğlu-ünal, Faika, Selin Cimok, Efe Doğukan Dincel, Lieve Naesens, ve Nuray Ulusoy Güzeldemirci. “Novel 4-Thiazolidinone Derivatives Bearing imidazo[2,1- b]thiazole Moiety: Design, Synthesis, and Antiviral Activity Evaluation”. Journal of Research in Pharmacy 27, sy. 2 (Haziran 2025): 924-35.
EndNote Başoğlu-ünal F, Cimok S, Dincel ED, Naesens L, Ulusoy Güzeldemirci N (01 Haziran 2025) Novel 4-thiazolidinone derivatives bearing imidazo[2,1- b]thiazole moiety: design, synthesis, and antiviral activity evaluation. Journal of Research in Pharmacy 27 2 924–935.
IEEE F. Başoğlu-ünal, S. Cimok, E. D. Dincel, L. Naesens, ve N. Ulusoy Güzeldemirci, “Novel 4-thiazolidinone derivatives bearing imidazo[2,1- b]thiazole moiety: design, synthesis, and antiviral activity evaluation”, J. Res. Pharm., c. 27, sy. 2, ss. 924–935, 2025.
ISNAD Başoğlu-ünal, Faika vd. “Novel 4-Thiazolidinone Derivatives Bearing imidazo[2,1- b]thiazole Moiety: Design, Synthesis, and Antiviral Activity Evaluation”. Journal of Research in Pharmacy 27/2 (Haziran 2025), 924-935.
JAMA Başoğlu-ünal F, Cimok S, Dincel ED, Naesens L, Ulusoy Güzeldemirci N. Novel 4-thiazolidinone derivatives bearing imidazo[2,1- b]thiazole moiety: design, synthesis, and antiviral activity evaluation. J. Res. Pharm. 2025;27:924–935.
MLA Başoğlu-ünal, Faika vd. “Novel 4-Thiazolidinone Derivatives Bearing imidazo[2,1- b]thiazole Moiety: Design, Synthesis, and Antiviral Activity Evaluation”. Journal of Research in Pharmacy, c. 27, sy. 2, 2025, ss. 924-35.
Vancouver Başoğlu-ünal F, Cimok S, Dincel ED, Naesens L, Ulusoy Güzeldemirci N. Novel 4-thiazolidinone derivatives bearing imidazo[2,1- b]thiazole moiety: design, synthesis, and antiviral activity evaluation. J. Res. Pharm. 2025;27(2):924-35.