Synthesis, and docking studies of novel tetrazole-S-alkyl derivatives as antimicrobial agents

References

• Kidd, T. J.; Canton, R.; Ekkelenkamp, M.; Johansen, H. K.; Gilligan, P.; LiPuma, J. J.; Bell, S. C.; Elborn, J. S.; Flume, P. A.; VanDevanter, D. R.; Waters, V. J. Defining Antimicrobial Resistance in Cystic Fibrosis. J. Cyst. Fibros 2018, 17, 696–704. DOI: 10.1016/j.jcf.2018.08.014.
   PubMed Web of Science ®Google Scholar
• Farooq, S.; Ngaini, Z. Microwave‐Assisted Synthesis, Antimicrobial Activities and Molecular Docking of Methoxycarboxylated Chalcone Derived Pyrazoline and Pyrazole Derivatives. Chem. Select 2022, 7, e202103984. DOI: 10.1002/slct.202103984.
   Google Scholar
• Nazariy, T. P.; Vasyl, S. M.; Mykola, D. O. New Convenient Synthesis of 2,3 Diaminotheino[2,3-d]Pyrimidin-4 (3H)-One Derivates from Substituted Alkyl 2-(1H-Tetrazol-1-yl)Thiophene-3-Carboxylates. Tetrahydron 2008, 64, 1430–1434. DOI: 10.1016/j.tet.2007.11.045.
   Web of Science ®Google Scholar
• Cheng-Xi, W.; Ming, B.; Guo-Hua, G. Tetrazolium Compounds: synthesis and Applications in Medicine. Molecules 2015, 20, 5528–5553. DOI: 10.3390/molecules20045528.
   PubMed Web of Science ®Google Scholar
• Kategaonkar, A. H.; Pokalwar, R. U.; Sonar, S. S.; Gawali, V. U.; Shingate, B. B.; Shingare, M. S. Synthesis, in Vitro Antibacterial and Antifungal Evaluations of New α-Hydroxyphosphonate and New α-Acetoxyphosphonate Derivatives of Tetrazolo[1,5- a]Quinolone. Eur. J. Med. Chem. 2010, 45, 1128–1132. DOI: 10.1016/j.ejmech.2009.12.013.
   PubMed Web of Science ®Google Scholar
• Bekhit, A. A.; El-Sayed, O. A.; Aboulmagd, E.; Park, J. Y. Tetrazolo[1,5-a]Quinoline as a Potential Promising New Scaffold for the Synthesis of Novel Anti-İnflammatory and Antibacterial Agents. Eur. J. Med. Chem. 2004, 39, 249–255. DOI: 10.1016/j.ejmech.2003.12.005.
   PubMed Web of Science ®Google Scholar
• Jedhe, G. S.; Paul, D.; Gonnade, R. G.; Santra, M. K.; Hamel, E.; Nguyen, T. L.; Sanjayan, G. J. Correlation of Hydrogen-Bonding Propensity and Anticancer Profile of Tetrazole-Tethered Combretastatin Analogues. Bioorg. Med. Chem. Lett. 2013, 23, 4680–4684. DOI: 10.1016/j.bmcl.2013.06.004.
   PubMed Web of Science ®Google Scholar
• Myznikov, L. V.; Hrabalek, A.; Koldobskii, G. I. Drugs in the Tetrazole Series. Chem. Heterocycl. Compd. 2007, 43, 1–9. DOI: 10.1007/s10593-007-0001-5.
   Google Scholar
• Mekheimer, R. A.; Abuo-Rahma, G. E. D. A.; Abd-Elmonem, M.; Yahia, R.; Hisham, M.; Hayallah, A. M.; Mostafa, S. M.; Abo-Elsoud, F. A.; Sadek, K. U. News-Triazine/Tetrazole Conjugates as Potent Antifungal and Antibacterial Agents: Design, Molecular Docking and Mechanistic Study. J. Mol. Struct. 2022, 1267, 133615. DOI: 10.1016/j.molstruc.2022.133615.
   Web of Science ®Google Scholar
• Demarinis, R. M.; Hoover, J. R. E.; Dunn, G. L.; Actor, P.; Uri, J. V.; Weisbach, J. A. A New Parenteral Cephalosporin. Sk&F 59962: 7-Trifluoromethylthioacetamido-3-(1-Methyl-1H-Tetrazol-5-Ylthiomethyl)-3-Cephem-4-Carboxylic Acid. Chemistry And Structure Activity Relationships. J. Antibiot. (Tokyo) 1975, 28, 463–465. DOI: 10.7164/antibiotics.28.463.
   PubMed Web of Science ®Google Scholar
• Sangal, S. K.; Ashok, Kumar, A. Synthesis of Some New Antifungal Tetrazolyl Sulphides. J. Indian Chem. Soc. 1986, 63, 351.
   Web of Science ®Google Scholar
• Alam, M.; Nami, S. A.; Husain, A.; Lee, D.; Park, S. Synthesis, Characterization, X-Ray Diffraction, Antimicrobial and İn Vitro Cytotoxicity Studies of 7a-Aza-B-Homostigmast-5-Eno [7a,7-d] Tetrazole. C. R. Chim. 2013, 16, 201–206. DOI: 10.1016/j.crci.2012.12.018.
   Web of Science ®Google Scholar
• Karabanovich, G.; Roh, J.; Smutný, T.; Němeček, J.; Vicherek, P.; Stolaříková, J.; Vejsová, M.; Dufková, I.; Vávrová, K.; Pávek, P.; et al. 1-Substituted-5-[(3,5-Dinitrobenzyl)Sulfanyl]-1H-Tetrazoles and Their İsostericanalogs: A New Class of Selective Antitubercular Agents Active against Drug-Susceptible and Multidrug-Resistant Mycobacteria. Eur. J. Med. Chem. 2014, 82, 324–323. DOI: 10.1016/j.ejmech.2014.05.069.
   PubMed Web of Science ®Google Scholar
• Pegklidou, K.; Koukoulitsa, C.; Nicolaou, I.; Demopoulos, V. J. Design and Synthesis of Novel Series of Pyrrole Based Chemotypes and Their Evaluation as Selective Aldose Reductase İnhibitors. A Case of Bioisosterism between a Carboxylic Acid Moiety and That of a Tetrazole. Bioorg. Med. Chem. 2010, 18, 2107–2114. DOI: 10.1016/j.bmc.2010.02.010.
   PubMedGoogle Scholar
• Guo, C. C.; Tong, R. B.; Li, K. L. Chloroalkyl Piperazine and Nitrogen Mustard Porphyrins: synthesis and Anticancer Activity. Bioorg. Med. Chem. 2004, 12, 2469–2475. DOI: 10.1016/j.bmc.2004.01.045.
   PubMed Web of Science ®Google Scholar
• Vitaku, E.; Smith, D. T.; Njardarson, J. T. Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals. J. Med. Chem. 2014, 57, 10257–10274. DOI: 10.1021/jm501100b.
   PubMed Web of Science ®Google Scholar
• Vo, C. V. T.; Bode, J. W. Synthesis of Saturated N-Heterocycles. J. Org. Chem. 2014, 79, 2809–2815. DOI: 10.1021/jo5001252.
   PubMed Web of Science ®Google Scholar
• Kanth, S.; Nagaraja, A.; Puttaiahgowda, Y. M. Polymeric Approach to Combat Drug-Resistant Methicillin-Resistant Staphylococcus aureus. J. Mater. Sci. 2021, 56, 7265–7285. DOI: 10.1007/s10853-021-05776-7.
   PubMed Web of Science ®Google Scholar
• Jalageri, M. D.; Puttaiahgowda.; Y. M.; Hariprasad. Design and Antimicrobial Activity of Piperazine Polymer Nanocomposite. Mater. Today: Proc. 2019, 15, 262–267. DOI: 10.1016/j.matpr.2019.05.003.
   Google Scholar
• Akshatha, N.; Yashoda, M. P. Synthesis of Environmental-Friendly Polymer Nanocomposite against Pathogenic Microorganism. Mater. Today: Proc. 2019, 15, 273–276. DOI: 10.1016/j.matpr.2019.05.005.
   Google Scholar
• Liu, H.; Huang, J.; Wang, J.; Wang, I.; Liu, M.; Wang, B.; Guo, H.; Lu, Y. Synthesis, Antimycobacterial and Antibacterial Evaluation of l-[(1R, 2S)-2-Fluorocyclopropyl]Fluoroquinolone Derivatives Containing an Oxime Functional Moiety. Eur. J. Med. Chem. 2014, 86, 628–638. DOI: 10.1016/j.ejmech.2014.09.029.
   PubMed Web of Science ®Google Scholar
• Yolal, M.; Basoglu, S.; Bektas, H.; Demirci, S.; Karaoglu, S. A.; Demirbas, A. Synthesis of Eperezolid-like Molecules and Evaluation of Their Antimicrobial Activities. Russ. J. Bioorg. Chem. 2012, 5, 539–549. DOI: 10.1134/S106816201205010X.
   Google Scholar
• Wang, X.; Wei, W.; Wang, P.; Tang, Y. T.; Deng, R. C.; Li, B.; Zhou, S. S.; Zhang, J. W.; Zhang, L.; Xiao, Z. P.; et al.Novel 3-Arylfuran-2(5H)-One-Fluoroquinolone Hybrid: Design, Synthesis and Evaluation as Antibacterial Agent. Bioorg. Med. Chem. 2014, 22, 3620–3628. DOI: 10.1016/j.bmc.2014.05.018.
   PubMed Web of Science ®Google Scholar
• Upadhayaya, R. S.; Sinha, N.; Jain, S.; Kishore, N.; Chandra, R.; Arora, S. K. Optically Active Antifungal Azoles: Synthesis and Antifungal Activity of (2R,3S)-2-(2,4-di-Fluorophenyl)-3-(5-{2-[4-Aryl-Piperazin-1-yl]-Ethyl}-Tetrazol-2-yl/1-yl)-1-[1,2,4]- Triazol-1-yl-Butan-2-ol. Bioorg. Med. Chem. 2004, 12, 2225–2238. DOI: 10.1016/j.bmc.2004.02.014.
   PubMed Web of Science ®Google Scholar
• Basoglu, S.; Ulker, S.; Alpay-Karaoglu, S.; Demirbas, N. Microwave-Assisted Synthesis of Some Hybrid Molecules Containing Penicillanic Acid or Cephalosporanic Acid Moieties and İnvestigation of Their Biological Activities. Med. Chem. Res. 2014, 23, 3128–3143. DOI: 10.1007/s00044-013-0898-4.
   PubMed Web of Science ®Google Scholar
• Teng, Y.; Zhou, Q. X.; Gao, P. Applications and Challenges of Elemental Sulfur, Nanosulfur, Polymeric Sulfur, Sulfur Composites, and Plasmonic Nanostructures. CRC Crit. Rev. Environ. Control 2019, 49, 2314–2358. DOI: 10.1080/10643389.2019.1609856.
   Web of Science ®Google Scholar
• Shankar, S.; Pangeni, R.; Park, J. W.; Rhim, J. W. Preparation of Sulfur Nanoparticles and Their Antibacterial Activity and Cytotoxic Effect. Mater. Sci. Eng. C Mater. Biol. Appl. 2018, 92, 508–517. DOI: 10.1016/j.msec.2018.07.015.
   PubMed Web of Science ®Google Scholar
• Zimmerman, M. T.; Bayse, C. A.; Ramoutar, R. R.; Brumaghim, J. L. Sulfur and Selenium Antioxidants: challenging Radical Scavenging Mechanisms and Developing Structure-Activity Relationships Based on Metal Binding. J. Inorg. Biochem. 2015, 145, 30–40. DOI: 10.1016/j.jinorgbio.2014.12.020.
   PubMed Web of Science ®Google Scholar
• Li, P.; Tian, P. Y.; Chen, Y. Z.; Song, X. P.; Xue, W.; Jin, L. H.; Hu, D. Y.; Yang, S.; Song, B. Novel Bisthioether Derivatives Containing a 1,3,4-Oxadiazole Moiety: Design, Synthesis, Antibacterial and Nematocidal Activities. Pest Manag. Sci. 2018, 74, 844–852. doi:10.1002/ps.476229024290.
   PubMed Web of Science ®Google Scholar
• Schenone, S.; Bruno, O.; Ranise, A.; Bondavalli, F.; Filippelli, W.; Rossi, F.; Falcone, G. Synthesis and Anti-İnflammatory Activity of Esters Derived from 5-Aryl-1,2-Dihydro-2-(2-Hydroxyethyl)-3H-1,2,4-Triazole-3-Thiones. II Farmaco 1998, 53, 590–593. DOI: 10.1016/S0014-827X(98)00074-3.
   PubMedGoogle Scholar
• Gülerman, N. N.; Dogan, H. N.; Rollas, S.; Johansson, C.; Celik, C. Synthesis and Structure Elucidation of Some New Thioether Derivatives of 1,2,4-Triazoline-3-Thiones and Their Antimicrobial Activities. Farmaco 2001, 56, 953–958. DOI: 10.1016/S0014-827X(01)01167-3.[PMC].[11829116.
   PubMedGoogle Scholar
• Li, Y. H.; Zhang, B.; Yang, H. K.; Li, Q.; Diao, P. C.; You, W. W.; Zhao, P. L. Design, Synthesis and Biological Evaluation of Novel Alkylsulfanyl-1,2,4-Triazoles as Cis-Restricted Combretastatin A-4 Analogues. Eur. J. Med. Chem. 2017, 125, 1098–1106. DOI: 10.1016/j.ejmech.2016.10.051.
   PubMed Web of Science ®Google Scholar
• Maertens, J. A. History of the Development of Azole Derivatives. Clin. Microbiol. Infect. 2004, 10, 1–10. DOI: 10.1111/j.1470-9465.2004.00841.x.
   PubMed Web of Science ®Google Scholar
• Kawsar, S. M.; Hosen, M. A.; El Bakri, Y.; Ahmad, S.; Affi, S. T.; Goumri-Said, S. In Silico Approach for Potential Antimicrobial Agents through Antiviral, Molecular Docking, Molecular Dynamics, Pharmacokinetic and Bioactivity Predictions of Galactopyranoside Derivatives. Arab. J. Basic Appl. Sci. 2022, 29, 99–112. DOI: 10.1080/25765299.2022.2068275.
   Google Scholar
• Çevik, U. A.; Celik, I.; Mella, J.; Mellado, M.; Özkay, Y.; Kaplancıklı, Z. A. Design, Synthesis, and Molecular Modeling Studies of a Novel Benzimidazole as an Aromatase Inhibitor. ACS Omega 2022, 7, 16152–16163. DOI: 10.1021/acsomega.2c01497.
   PubMed Web of Science ®Google Scholar
• Acar Çevik, U.; Sağlık, B. N.; Osmaniye, D.; Levent, S.; Kaya Çavuşoğlu, B.; Karaduman, A. B.; Atlı Eklioğlu, Ö.; Özkay, Y.; Kaplancıklı, Z. A. Synthesis, Anticancer Evaluation and Molecular Docking Studies of New Benzimidazole-1,3,4-Oxadiazole Derivatives as Human Topoisomerase Types I Poison. J. Enzyme Inhib. Med. Chem. 2020, 35, 1657–1673. DOI: 10.1080/14756366.2020.1806831.
   PubMed Web of Science ®Google Scholar
• Çevik, U. A.; Celik, I.; Işık, A.; Pillai, R. R.; Tallei, T. E.; Yadav, R.; Ozkay, Y.; Kaplancıklı, Z. A. Synthesis, Molecular Modeling, Quantum Mechanical Calculations and ADME Estimation Studies of Benzimidazole-Oxadiazole Derivatives as Potent Antifungal Agents. J. Mol. Struct. 2022, 1252, 132095. DOI: 10.1016/j.molstruc.2021.132095.
   Web of Science ®Google Scholar
• Hargrove, T. Y.; Friggeri, L.; Wawrzak, Z.; Qi, A.; Hoekstra, W. J.; Schotzinger, R. J.; York, J. D.; Guengerich, F. P.; Lepesheva, G. I. Structural Analyses of Candida albicans Sterol 14α-Demethylase Complexed with Azole Drugs Address the Molecular Basis of Azole-Mediated İnhibition of Fungal Sterol Biosynthesis. J. Biol. Chem. 2017, 292, 6728–6743. DOI: 10.1074/jbc.M117.778308.
   PubMed Web of Science ®Google Scholar
• Repasky, M. P.; Murphy, R. B.; Banks, J. L.; Greenwood, J. R.; Tubert-Brohman, I.; Bhat, S.; Friesner, R. A. Docking Performance of the Glide Program as Evaluated on the Astex and DUD Datasets: A Complete Set of Glide SP Results and Selected Results for a New Scoring Function İntegrating WaterMap and Glide. J. Comput. Aided Mol. Des. 2012, 26, 787–799. DOI: 10.1007/s10822-012-9575-9.
   PubMed Web of Science ®Google Scholar