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Research Article

Synthesis of new benzimidazole derivatives containing 1,3,4-thiadiazole: their in vitro antimicrobial, in silico molecular docking and molecular dynamic simulations studies

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Pages 899-914 | Received 27 Sep 2022, Accepted 14 Nov 2022, Published online: 24 Nov 2022

References

  • D.M. Livermore, M. Warner, S. Mushtaq, M. Doumith, J. Zhang, and N. Woodford, What remains against carbapenem-resistant enterobacteriaceae? Evaluation of chloramphenicol, ciprofloxacin, colistin, fosfomycin, minocycline, nitrofurantoin, temocillin and tigecycline, Int. J. Antimicrob. Agents 37 (2011), pp. 415–419. doi:10.1016/j.ijantimicag.2011.01.012.
  • S. Basak, P. Singh, and M. Rajurkar, Multidrug resistant and extensively drug resistant bacteria: A study, J. Pathog. 2016 (2016), pp. 1–5. doi:10.1155/2016/4065603.
  • B. Walker, S. Barrett, S. Polasky, V. Galaz, C. Folke, G. Engström, F. Ackerman, K. Arrow, S. Cerpenter, K. Chopra, G. Daily, P. Ehrlich, T. Hughes, N. Kautsky, S. Levin, K.G. Maler, J. Shogren, J. Vincent, T. Xepepedeas, and A. De Zeeuw, Looming global-scale failures and missing institutions, Science 325 (2009), pp. 1345–1346. doi:10.1126/science.1175325.
  • N.S. El-Gohary and M.I. Shaaban, Synthesis and biological evaluation of a new series of benzimidazole derivatives as antimicrobial, antiquorum-sensing and antitumor agents, Eur. J. Med. Chem. 131 (2017), pp. 255–262. doi:10.1016/j.ejmech.2017.03.018.
  • U. Theuretzbacher, Future antibiotics scenarios: Is the tide starting to turn? Int. J. Antimicrob. Agents. 34 (2009), pp. 15–20. doi:10.1016/j.ijantimicag.2009.02.005.
  • M.M. Azevedo, R. Teixeira-Santos, A.P. Silva, L. Cruz, E. Ricardo, C. Pina-Vaz, and A.G. Rodrigues, The effect of antibacterial and non-antibacterial compounds alone or associated with antifugals upon fungi, Front. Microbiol. 6 (2015), pp. 669. doi:10.3389/fmicb.2015.00669.
  • E. Vitaku, D.T. Smith, and J.T. Njardarson, Analysis of the structural diversity, substitution patterns, and frequency of nitrogen heterocycles among US FDA approved pharmaceuticals: Miniperspective, J. Med. Chem. 57 (2014), pp. 10257–10274. doi:10.1021/jm501100b.
  • Y. Li, C. Tan, C. Gao, C. Zhang, X. Luan, X. Chen, Y. Liu, H. Chen, and Y. Jiang, Discovery of benzimidazole derivatives as novel multi-target EGFR, VEGFR-2 and PDGFR kinase inhibitors, Bioorg. Med. Chem. 19 (2011), pp. 4529–4535. doi:10.1016/j.bmc.2011.06.022.
  • S. Tahlan, K. Ramasamy, S.M. Lim, S.A.A. Shah, V. Mani, and B. Narasimhan, Design, synthesis and therapeutic potential of 3-(2-(1H-benzo [d] imidazol-2-ylthio) acetamido)-N-(substituted phenyl) benzamide analogues, Chem. Cent. J. 12 (2018), pp. 1–12. doi:10.1186/s13065-018-0513-3.
  • B.V. Jain, M.R.M. Usman, S.R. Pawar, N.R. Patil, P.J. Patil, and S.N. Sharma, A vegetarian capsule: A review, Int. J. Pharm. Technol. 2 (2012), pp. 10–12.
  • H.B. El-Nassan, Synthesis, antitumor activity and SAR study of novel [1,2,4] triazino [4,5-a] benzimidazole derivatives, Eur. J. Med. Chem. 53 (2012), pp. 22–27. doi:10.1016/j.ejmech.2012.03.028.
  • P.T.M. Nguyen, J.D. Baldeck, J. Olsson, and R.E. Marquis, Antimicrobial actions of benzimidazoles against oral streptococci, Oral Microbiol. Immunol 20 (2005), pp. 93–100. doi:10.1111/j.1399-302X.2004.00197.x.
  • J. Gowda, A.M.A. Khader, B. Kalluraya, and S. Hidayathulla, Synthesis, characterization and antibacterial activity of benzimidazole derivatives carrying quinoline moiety, Indian J. Chem. 50B (2011), pp. 1491–1495.
  • B.V.S. Kumar, S.D. Vaidya, R.V. Kumar, S.B. Bhirud, and R.B. Mane, Synthesis and anti-bacterial activity of some novel 2-(6-fluorochroman-2-yl)-1-alkyl/acyl/aroyl-1H-benzimidazoles, Eur. J. Med. Chem. 41 (2006), pp. 599–604. doi:10.1016/j.ejmech.2006.01.006.
  • Y. Özkay, Y. Tunalı, H. Karaca, and İ. Işıkdağ, Antimicrobial activity and a SAR study of some novel benzimidazole derivatives bearing hydrazone moiety, Eur. J. Med. Chem. 45 (2010), pp. 3293–3298. doi:10.1016/j.ejmech.2010.04.012.
  • B.G. Youssif, S.G. Abdel-Moty, and I.M. Sayed, Synthesis and biological evaluation of some novel 1, 2, 3-triazol-N-arylidene Acetohydrazide incorporating benzimidazole ring moiety as potential antimicrobial agents, J. Curr. Chem. Pharm. Sci. 4 (2014), pp. 54–64.
  • N.S. Pawar, D.S. Dalal, S.R. Shimpi, and P.P. Mahulikar, Studies of antimicrobial activity of N-alkyl and N-acyl 2-(4-thiazolyl)-1H-benzimidazoles, Eur. J. Pharm. Sci. 21 (2004), pp. 115–118. doi:10.1016/j.ejps.2003.09.001.
  • K.F. Ansari and C. Lal, Synthesis, physicochemical properties and antimicrobial activity of some new benzimidazole derivatives, Eur. J. Med. Chem. 44 (2009), pp. 4028–4033. doi:10.1016/j.ejmech.2009.04.037.
  • E. Menteşe, F. Yılmaz, N. Baltaş, O. Bekircan, and B. Kahveci, Synthesis and antioxidant activities of some new triheterocyclic compounds containing benzimidazole, thiophene, and 1,2,4-triazole rings, J. Enzyme Inhib. Med. Chem. 30 (2015), pp. 435–441. doi:10.3109/14756366.2014.943203.
  • E. Menteşe, F. Yılmaz, M. Emirik, S. Ülker, and B. Kahveci, Synthesis, molecular docking and biological evaluation of some benzimidazole derivatives as potent pancreatic lipase inhibitors, Bioorg. Chem. 76 (2018), pp. 478–486. doi:10.1016/j.bioorg.2017.12.023.
  • T. Elavarasan, D.P. Bhakiaraj, and M. Gopalakrishnan, Synthesis, spectral analysis, in vitro microbiological evaluation, and molecular docking studies of some novel 1-(1-aryl-1H-tetrazol-5-yl)-2-(piperidin-1-yl) ethanone derivatives, Int. Sch. Res. Notices 2014 (2014), pp. 1–9.
  • D. Łowicki and P. Przybylski, Cascade synthetic strategies opening access to medicinal-relevant aliphatic 3-and 4-membered N-heterocyclic scaffolds, Eur. J. Med. Chem. 238 (2022), pp. 114438. doi:10.1016/j.ejmech.2022.114438.
  • D. Łowicki and P. Przybylski, Tandem construction of biological relevant aliphatic 5-membered N-heterocycles, Eur. J. Med. Chem. 235 (2022), pp. 114303. doi:10.1016/j.ejmech.2022.114303.
  • W. Huang, P.L. Zhao, C.L. Liu, Q. Chen, Z.M. Liu, and G.F. Yang, Design, synthesis, and fungicidal activities of new strobilurin derivatives, J. Agric. Food Chem. 55 (2007), pp. 3004–3010. doi:10.1021/jf0632987.
  • L. Yang, Q. Liu, H. Liu, D. Chen, H. Li, Z. Chen, and W. Xu, Synthesis and antimicrobial bioassays of 1,3,4-thiadiazole sulfone derivatives containing amide moiety: A study based on molecular dynamics (MD) simulations, MM/GBSA, and molecular docking, J. Saudi Chem. Soc. 26 (2022), pp. 101415. doi:10.1016/j.jscs.2021.101415.
  • M.A. Wikler, Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically: Approved standard, CLSI (Nccls), 26 (2006), pp. M7–A7.
  • A. Espinel-Ingroff, B. Arthington-Skaggs, N. Iqbal, D. Ellis, M.A. Pfaller, S. Messer, M. Rinaldi, A. Fothergill, D.L. Gibbs, and A. Wang, Multicenter evaluation of a new disk agar diffusion method for susceptibility testing of filamentous fungi with voriconazole, posaconazole, itraconazole, amphotericin B, and caspofungin, J. Clin. Microbiol. 45 (2007), pp. 1811–1820. doi:10.1128/JCM.00134-07.
  • A.E. Evren, L. Yurttas, and M. Yılmaz-Cankilic, Synthesis of novel N -(naphthalen-1-yl)propanamide derivatives and evaluation their antimicrobial activity, Phosphorus Sulfur Silicon Relat. Elem. 195 (2020), pp. 158–164. doi:10.1080/10426507.2019.1657428.
  • Maestro. Schrödinger, Schrödinger Release 2020-3. Schrödinger, LLC, New York, NY, 2020. https://www.schrodinger.com.tr/products/maestro
  • LigPrep. Schrödinger, Schrödinger Release 2020-3. Schrödinger, LLC, New York, NY, 2020. https://www.schrodinger.com.tr/products/ligprep
  • Glide. Schrödinger, Schrödinger Release 2020-3, Schrödinger, LLC, New York, NY, 2020. https://www.schrodinger.com.tr/products/glide
  • Desmond Molecular Dynamics System. D. E. Shaw Research. Maestro-Desmond Interoperability Tools, Schrödin-ger, New York, NY, 2021. https://www.schrodinger.com/products/desmond
  • B. Eren and Y. Bekdemir, Simple, mild, and highly efficient synthesis of 2-substituted benzimidazoles and bis-benzimidazoles, Quím. Nova. 37 (2014), pp. 643–647. doi:10.5935/0100-4042.20140096.
  • K.J. Fishel, A.L. Gulledge, A.T. Pingitore, J.P. Hoffman, W.P. Steckle Jr, and B.C. Benicewicz, Solution polymerization of polybenzimidazole, J. Polym. Sci. 54 (2016), pp. 1795–1802. doi:10.1002/pola.28041.
  • H.A. Abdel-Aziz, T. Elsaman, M.I. Attia, and A.M. Alanazi, The reaction of ethyl 2-oxo-2 H-chromene-3-carboxylate with hydrazine hydrate, Molecules 18 (2013), pp. 2084–2095. doi:10.3390/molecules18022084.
  • D. Roy, K. Todd, and M. John, Gauss View, Semichem. Inc., Shawnee Mission, KS, USA, 2009. ( Version 5).
  • I. Celik, G. Ayhan‐Kılcıgil, A. Karayel, B. Guven, and A. Onay‐Besikci, Synthesis, molecular docking, in silico ADME, and EGFR kinase inhibitor activity studies of some new benzimidazole derivatives bearing thiosemicarbazide, triazole, and thiadiazole, J. Heterocyclic Chem. 59 (2022), pp. 371–387. doi:10.1002/jhet.4431.
  • Y. Hu, C.Y. Li, X.M. Wang, Y.H. Yang, and H.L. Zhu, 1,3,4-Thiadiazole: Synthesis, reactions, and applications in medicinal, agricultural, and materials chemistry, Chem. Rev. 114 (2014), pp. 5572–5610. doi:10.1021/cr400131u.
  • D.R. Guda, H.M. Cho, and M.E. Lee, Mild and convenient one-pot synthesis of 2-amino-1, 3, 4-thiadiazoles using trimethylsilyl isothiocyanate (TMSNCS), RSC Adv. 3 (2013), pp. 6813–6816. doi:10.1039/c3ra00159h.
  • I. Çoruh, S. Rollas, S. Turan, and J. Akbuğa, Synthesis and evaluation of cytotoxic activities of some 1, 4-disubstituted thiosemicarbazides, 2,5-disubstituted-1,3,4-thiadiazoles and 1,2,4-triazole-5-thiones derived from benzilic acid hydrazide, Marmara Pharma. J. 1 (2012), pp. 56–63. doi:10.12991/201216421.
  • A.E. Evren, S. Dawbaa, N.U.H.A. Demokrat, Ş.A. Yavuz, Ü.D. Gül, and L. Yurttaş, Design and synthesis of new 4-methylthiazole derivatives: In vitro and in silico studies of antimicrobial activity, J. Mol. Struct. 1241 (2021), pp. 130692. doi:10.1016/j.molstruc.2021.130692.
  • A.A. Adhreai, M. ALSaeedy, M. Farooqui, A. Alrabie, I. Al-Qadsy, and U. Al-Timari, Stereoselective synthesis of novel chiral open-chain d-ribose and d-glucose-derived nitrones through 1, 3-dipolar cycloaddition of maleimide and maleic acid and investigation of their antimicrobial activity via molecular docking and ADMET studies, J. Mol. Struct. 1256 (2022), pp. 132481. doi:10.1016/j.molstruc.2022.132481.
  • X.C. Yang, P.L. Zhang, K.V. Kumar, S. Li, R.X. Geng, and C.H. Zhou, Discovery of unique thiazolidinone-conjugated coumarins as novel broad spectrum antibacterial agents, Eur. J. Med. Chem. 232 (2022), pp. 114192. doi:10.1016/j.ejmech.2022.114192.
  • M. Brvar, A. Perdih, M. Renko, G. Anderluh, D. Turk, and T. Solmajer, Structure-based discovery of substituted 4, 5′-bithiazoles as novel DNA gyrase inhibitors, J. Med. Chem. 55 (2012), pp. 6413–6426. doi:10.1021/jm300395d.
  • S.S. Ahmad, M. Sinha, K. Ahmad, M. Khalid, and I. Choi, Study of Caspase 8 inhibition for the management of Alzheimer’s disease: A molecular docking and dynamics simulation, Molecules 25 (2020), pp. 2071. doi:10.3390/molecules25092071.

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