Research Article
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Synthesis, biological activity evaluation and molecular docking studies of novel thiazole derivatives

Year 2023, Volume: 2 Issue: 1, 1 - 24, 24.04.2023

Derya Osmaniye Uğur Kayiş Ülküye Dudu Gül Yusuf Özkay Zafer Asım Kaplancıklı

https://doi.org/10.55971/EJLS.1270394

Abstract

Resistance to existing drugs develops because of insensible use of antibacterial and antifungal drugs. Therefore, there is a need for the development of new drug candidate compounds. The thiazole ring has many biological activities. It is possible to include antibacterial and antifungal activities among these activities. In addition to these, the thiazole ring has been preferred because it is the bioisostere of the imidazole ring in the structure of many antifungal drugs. For this purpose, within the scope of this study, 7 new thiazole compounds were synthesized, and their structure determinations were carried out using HRMS, 1H-NMR, 13C-NMR spectroscopic methods. Their antibacterial and antifungal activities were investigated by in vitro methods. As a result of activity tests, compound 3e showed activity against C.krusei strain with MIC50=31.25 ug/mL. The potential effectiveness of the compound 3e on the 14alpha-demethylase enzyme (PDB ID:3LD6) was tested by in silico studies.

Keywords

Thiazole Antibacterial Activity Antifungal Activity Molecular Docking

Thanks

As the authors of this study, we thank Anadolu University Faculty of Pharmacy Central Laboratory for their support and contributions.

References

  • Yang XC, Zeng CM, Avula SR, Peng XM, Geng RX, Zhou CH. Novel coumarin aminophosphonates as potential multitargeting antibacterial agents against Staphylococcus aureus. Eur. J. Med. Chem. (2023); 245: 114891. https://doi.org/10.1016/j.ejmech.2022.114891
  • Zhou XM, Hu YY, Fang B, Zhou CH. Benzenesulfonyl thiazoloimines as unique multitargeting antibacterial agents towards Enterococcus faecalis. Eur. J. Med. Chem. (2023); 115088. https://doi.org/10.1016/j.ejmech.2023.115088
  • Rashdan HR, Abdelmonsef AH, Abou-Krisha MM, Yousef TA. Synthesis, identification, computer-aided docking studies, and ADMET prediction of novel benzimidazo-1, 2, 3-triazole based molecules as potential antimicrobial agents. Molecules (2021); 26(23): 7119. https://doi.org/10.3390/molecules26237119
  • Niu ZX, Wang YT, Zhang SN, Li Y, Chen XB, Wang SQ, Liu HM. Application and synthesis of thiazole ring in clinically approved drugs. Eur. J. Med. Chem (2023); 250: 115172. https://doi.org/10.1016/j.ejmech.2023.115172
  • Hussein AHM, El-Adasy ABA, El-Saghier AM, Olish M, Abdelmonsef AH. Synthesis, characterization, in silico molecular docking, and antibacterial activities of some new nitrogen-heterocyclic analogues based on ap-phenolic unit. RSC Adv. (2022); 12(20): 12607-12621. https://doi.org/10.1039%2Fd2ra01794f
  • Mokariya JA, Rajani DP, Patel MP. 1, 2, 4‐Triazole and benzimidazole fused dihydropyrimidine derivatives: Design, green synthesis, antibacterial, antitubercular, and antimalarial activities. Arch. Pharm. (2022); e2200545. https://doi.org/10.1002/ardp.202200545
  • Nural Y, Ozdemir S, Yalcin MS, Demir B, Atabey H, Seferoglu Z, Ece A. New bis-and tetrakis-1, 2, 3-triazole derivatives: Synthesis, DNA cleavage, molecular docking, antimicrobial, antioxidant activity and acid dissociation constants. Bioorg. Med. Chem. Lett. (2022); 55: 128453. https://doi.org/10.1016/j.bmcl.2021.128453
  • Hu Y, Hu C, Pan G, Yu C, Ansari MF, Bheemanaboina RRY, Cheng Y, Chenghe Z, Zhang, J. Novel chalcone-conjugated, multi-flexible end-group coumarin thiazole hybrids as potential antibacterial repressors against methicillin-resistant Staphylococcus aureus. Eur. J. Med. Chem. (2021); 222: 113628. https://doi.org/10.1016/j.ejmech.2021.113628
  • Sucharitha ER, Krishna TM, Manchal R, Ramesh G, Narsimha S. Fused benzo [1, 3] thiazine-1, 2, 3-triazole hybrids: Microwave-assisted one-pot synthesis, in vitro antibacterial, antibiofilm, and in silico ADME-studies. Bioorg. Med. Chem. Lett. (2021); 47: 128201. https://doi.org/10.1016/j.bmcl.2021.128201
  • Gondru R, Kanugala S, Raj S, Kumar CG, Pasupuleti M, Banothu J, Bavantula R. 1, 2, 3-triazole-thiazole hybrids: Synthesis, in vitro antimicrobial activity and antibiofilm studies. Bioorg. Med. Chem. Lett. (2021); 33: 127746. https://doi.org/10.1016/j.bmcl.2020.127746
  • Salih RHH, Hasan AH, Hussen NH, Hawaiz FE, Hadda TB, Jamalis J, Almalki FA, Adeyinka AS, Coetzee LCC, Oyebamiji, AK. Thiazole-pyrazoline hybrids as potential antimicrobial agent: synthesis, biological evaluation, molecular docking, DFT studies and POM-analysis. J. Mol. Struct. (2023); 1282(10): 135191. https://doi.org/10.1016/j.molstruc.2023.135191
  • Alqurashi RM, Farghaly TA, Sabour R, Shaabana MR. Design, Synthesis, antimicrobial screening and molecular modeling of novel 6, 7 dimethylquinoxalin-2 (1H)-one and thiazole derivatives targeting DNA gyrase enzyme. Bioorg. Chem. (2023); 134: 106433. https://doi.org/10.1016/j.bioorg.2023.106433
  • Nandurkar Y, Shinde A, Bhoye MR, Jagadale S, Mhaske PC. Synthesis and biological screening of new 2-(5-Aryl-1-phenyl-1H-pyrazol-3-yl)-4-aryl thiazole derivatives as potential antimicrobial agents. ACS Omega (2023); 8(9):8743-8754. https://doi.org/10.1021/acsomega.2c08137
  • Meng F, Yan Z, Lu Y, Wang X. Design, synthesis, and antifungal activity of flavonoid derivatives containing thiazole moiety. Chem. Pap. (2022); 77:877-885. https://doi.org/10.1007/s11696-022-02522-4
  • Jagadeesan S, Karpagam S. Novel series of N-acyl substituted indole based piperazine, thiazole and tetrazoles as potential antibacterial, antifungal, antioxidant and cytotoxic agents, and their docking investigation as potential Mcl-1 inhibitors. J. Mol. Struct. (2023); 1271: 134013. https://doi.org/10.1016/j.molstruc.2022.134013
  • Wikler MA. Methods for dilution antimicrobial susceptibility tests for bacteria that growl aerobically: approved standard. Clsi (Nccls) (2006); 26: M7-A7.
  • Evren AE, Dawbaa S, Nuha D, Yavuz ŞA, Gül ÜD, Yurttaş L. Design and synthesis of new 4-methylthiazole derivatives: In vitro and in silico studies of antimicrobial activity. J. Mol. Struct. (2021); 1241: 130692. https://doi.org/10.1016/j.molstruc.2021.130692
  • Swiss Institute of Bioinformatics. SwissADME. Retrieved December 1 2022 from http://www.swissadme.ch/index.php#
  • Strushkevich N, Usanov SA, Park HW. Structural basis of human CYP51 inhibition by antifungal azoles. J. Mol. Biol. (2010); 397(4): 1067-1078. https://doi.org/10.1016/j.jmb.2010.01.075
  • Maestro, Schrödinger, LLC: New York, NY, USA 2020.
  • Schrödinger, Schrödinger, LLC, New York, NY, USA 2020.
  • Schrödinger, Schrödinger, LLC: New York, NY, USA 2020.
  • Borra RC, Lotufo MA, Gagioti SM, Barros FDM, Andrade PM. A simple method to measure cell viability in proliferation and cytotoxicity assays. Braz. Oral. Res. (2009); 23: 255-262. https://doi.org/10.1590/S1806-83242009000300006
  • Palomino JC, Martin A, Camacho M, Guerra H, Swings J, Portaels F. Resazurin microtiter assay plate: simple and inexpensive method for detection of drug resistance in Mycobacterium tuberculosis. AMACCQ (2022); 46(8): 2720-2722. https://doi.org/10.1128/AAC.46.8.2720-2722.2002
  • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. (2012); 64: 4-17. https://doi.org/10.1016/S0169-409X(00)00129-0
  • Daina A, Michielin O, Zoete V. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci. Rep. (2017); 7(1): 42717.

Year 2023, Volume: 2 Issue: 1, 1 - 24, 24.04.2023

Derya Osmaniye Uğur Kayiş Ülküye Dudu Gül Yusuf Özkay Zafer Asım Kaplancıklı

https://doi.org/10.55971/EJLS.1270394

Abstract

References

  • Yang XC, Zeng CM, Avula SR, Peng XM, Geng RX, Zhou CH. Novel coumarin aminophosphonates as potential multitargeting antibacterial agents against Staphylococcus aureus. Eur. J. Med. Chem. (2023); 245: 114891. https://doi.org/10.1016/j.ejmech.2022.114891
  • Zhou XM, Hu YY, Fang B, Zhou CH. Benzenesulfonyl thiazoloimines as unique multitargeting antibacterial agents towards Enterococcus faecalis. Eur. J. Med. Chem. (2023); 115088. https://doi.org/10.1016/j.ejmech.2023.115088
  • Rashdan HR, Abdelmonsef AH, Abou-Krisha MM, Yousef TA. Synthesis, identification, computer-aided docking studies, and ADMET prediction of novel benzimidazo-1, 2, 3-triazole based molecules as potential antimicrobial agents. Molecules (2021); 26(23): 7119. https://doi.org/10.3390/molecules26237119
  • Niu ZX, Wang YT, Zhang SN, Li Y, Chen XB, Wang SQ, Liu HM. Application and synthesis of thiazole ring in clinically approved drugs. Eur. J. Med. Chem (2023); 250: 115172. https://doi.org/10.1016/j.ejmech.2023.115172
  • Hussein AHM, El-Adasy ABA, El-Saghier AM, Olish M, Abdelmonsef AH. Synthesis, characterization, in silico molecular docking, and antibacterial activities of some new nitrogen-heterocyclic analogues based on ap-phenolic unit. RSC Adv. (2022); 12(20): 12607-12621. https://doi.org/10.1039%2Fd2ra01794f
  • Mokariya JA, Rajani DP, Patel MP. 1, 2, 4‐Triazole and benzimidazole fused dihydropyrimidine derivatives: Design, green synthesis, antibacterial, antitubercular, and antimalarial activities. Arch. Pharm. (2022); e2200545. https://doi.org/10.1002/ardp.202200545
  • Nural Y, Ozdemir S, Yalcin MS, Demir B, Atabey H, Seferoglu Z, Ece A. New bis-and tetrakis-1, 2, 3-triazole derivatives: Synthesis, DNA cleavage, molecular docking, antimicrobial, antioxidant activity and acid dissociation constants. Bioorg. Med. Chem. Lett. (2022); 55: 128453. https://doi.org/10.1016/j.bmcl.2021.128453
  • Hu Y, Hu C, Pan G, Yu C, Ansari MF, Bheemanaboina RRY, Cheng Y, Chenghe Z, Zhang, J. Novel chalcone-conjugated, multi-flexible end-group coumarin thiazole hybrids as potential antibacterial repressors against methicillin-resistant Staphylococcus aureus. Eur. J. Med. Chem. (2021); 222: 113628. https://doi.org/10.1016/j.ejmech.2021.113628
  • Sucharitha ER, Krishna TM, Manchal R, Ramesh G, Narsimha S. Fused benzo [1, 3] thiazine-1, 2, 3-triazole hybrids: Microwave-assisted one-pot synthesis, in vitro antibacterial, antibiofilm, and in silico ADME-studies. Bioorg. Med. Chem. Lett. (2021); 47: 128201. https://doi.org/10.1016/j.bmcl.2021.128201
  • Gondru R, Kanugala S, Raj S, Kumar CG, Pasupuleti M, Banothu J, Bavantula R. 1, 2, 3-triazole-thiazole hybrids: Synthesis, in vitro antimicrobial activity and antibiofilm studies. Bioorg. Med. Chem. Lett. (2021); 33: 127746. https://doi.org/10.1016/j.bmcl.2020.127746
  • Salih RHH, Hasan AH, Hussen NH, Hawaiz FE, Hadda TB, Jamalis J, Almalki FA, Adeyinka AS, Coetzee LCC, Oyebamiji, AK. Thiazole-pyrazoline hybrids as potential antimicrobial agent: synthesis, biological evaluation, molecular docking, DFT studies and POM-analysis. J. Mol. Struct. (2023); 1282(10): 135191. https://doi.org/10.1016/j.molstruc.2023.135191
  • Alqurashi RM, Farghaly TA, Sabour R, Shaabana MR. Design, Synthesis, antimicrobial screening and molecular modeling of novel 6, 7 dimethylquinoxalin-2 (1H)-one and thiazole derivatives targeting DNA gyrase enzyme. Bioorg. Chem. (2023); 134: 106433. https://doi.org/10.1016/j.bioorg.2023.106433
  • Nandurkar Y, Shinde A, Bhoye MR, Jagadale S, Mhaske PC. Synthesis and biological screening of new 2-(5-Aryl-1-phenyl-1H-pyrazol-3-yl)-4-aryl thiazole derivatives as potential antimicrobial agents. ACS Omega (2023); 8(9):8743-8754. https://doi.org/10.1021/acsomega.2c08137
  • Meng F, Yan Z, Lu Y, Wang X. Design, synthesis, and antifungal activity of flavonoid derivatives containing thiazole moiety. Chem. Pap. (2022); 77:877-885. https://doi.org/10.1007/s11696-022-02522-4
  • Jagadeesan S, Karpagam S. Novel series of N-acyl substituted indole based piperazine, thiazole and tetrazoles as potential antibacterial, antifungal, antioxidant and cytotoxic agents, and their docking investigation as potential Mcl-1 inhibitors. J. Mol. Struct. (2023); 1271: 134013. https://doi.org/10.1016/j.molstruc.2022.134013
  • Wikler MA. Methods for dilution antimicrobial susceptibility tests for bacteria that growl aerobically: approved standard. Clsi (Nccls) (2006); 26: M7-A7.
  • Evren AE, Dawbaa S, Nuha D, Yavuz ŞA, Gül ÜD, Yurttaş L. Design and synthesis of new 4-methylthiazole derivatives: In vitro and in silico studies of antimicrobial activity. J. Mol. Struct. (2021); 1241: 130692. https://doi.org/10.1016/j.molstruc.2021.130692
  • Swiss Institute of Bioinformatics. SwissADME. Retrieved December 1 2022 from http://www.swissadme.ch/index.php#
  • Strushkevich N, Usanov SA, Park HW. Structural basis of human CYP51 inhibition by antifungal azoles. J. Mol. Biol. (2010); 397(4): 1067-1078. https://doi.org/10.1016/j.jmb.2010.01.075
  • Maestro, Schrödinger, LLC: New York, NY, USA 2020.
  • Schrödinger, Schrödinger, LLC, New York, NY, USA 2020.
  • Schrödinger, Schrödinger, LLC: New York, NY, USA 2020.
  • Borra RC, Lotufo MA, Gagioti SM, Barros FDM, Andrade PM. A simple method to measure cell viability in proliferation and cytotoxicity assays. Braz. Oral. Res. (2009); 23: 255-262. https://doi.org/10.1590/S1806-83242009000300006
  • Palomino JC, Martin A, Camacho M, Guerra H, Swings J, Portaels F. Resazurin microtiter assay plate: simple and inexpensive method for detection of drug resistance in Mycobacterium tuberculosis. AMACCQ (2022); 46(8): 2720-2722. https://doi.org/10.1128/AAC.46.8.2720-2722.2002
  • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. (2012); 64: 4-17. https://doi.org/10.1016/S0169-409X(00)00129-0
  • Daina A, Michielin O, Zoete V. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Sci. Rep. (2017); 7(1): 42717.
There are 26 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences
Journal Section Research Articles
Authors

Derya Osmaniye 0000-0002-0499-436X

Uğur Kayiş 0000-0003-0020-0857

Ülküye Dudu Gül 0000-0001-6443-1633

Yusuf Özkay 0000-0001-8815-153X

Zafer Asım Kaplancıklı 0000-0003-2252-0923

Publication Date April 24, 2023
Submission Date March 24, 2023
Published in Issue Year 2023 Volume: 2 Issue: 1

Cite

Vancouver Osmaniye D, Kayiş U, Gül ÜD, Özkay Y, Kaplancıklı ZA. Synthesis, biological activity evaluation and molecular docking studies of novel thiazole derivatives. Eur J Life Sci. 2023;2(1):1-24.
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