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Research Articles

Design, synthesis, antimicrobial activity and in silico molecular docking studies of some sulfur containing pyrazole-pyridine hybrids

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Pages 1226-1237 | Received 24 Jan 2022, Accepted 30 May 2022, Published online: 09 Jun 2022

References

  • Manjal, S. K.; Kaur, R.; Bhatia, R.; Kumar, K.; Singh, V.; Shankar, R.; Kaur, R.; Rawal, R. K. Synthetic and Medicinal Perspective of Thiazolidinones: A Review. Bioorg. Chem. 2017, 75, 406–423. DOI: 10.1016/j.bioorg.2017.10.014.
  • Pathania, S.; Narang, R. K.; Rawal, R. K. Role of Sulphur-Heterocycles in Medicinal Chemistry: An Update. Eur. J. Med. Chem. 2019, 180, 486–508. DOI: 10.1016/j.ejmech.2019.07.043.
  • Feng, M.; Tang, B.; Liang, S. H.; Jiang, X. Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry. Curr. Top. Med. Chem. 2016, 16, 1200–1216.
  • Schutte, L.; Teranishi, R. Precursors of Sulfur‐Containing Flavor Compounds. Crit. Rev. Food Sci. Nutr. 1974, 4, 457–505. DOI: 10.1080/104083974095271666.
  • Kim, D. E.; Kim, Y.; Cho, D.-H.; Jeong, S.-Y.; Kim, S.-B.; Suh, N.; Lee, J. S.; Choi, E. K.; Koh, J.-Y.; Hwang, J. J.; Kim, C.-S. Raloxifene Induces Autophagy-Dependent Cell Death in Breast Cancer Cells via the Activation of Amp-Activated Protein Kinase. Mol. Cells 2015, 38, 138–144. DOI: 10.14348/molcells.2015.2193.
  • Nayak, K. R.; Cavendish, J. J. Risk Reduction with Clopidogrel in the Management of Peripheral Arterial Disease. Vasc. Health Risk Manage. 2007, 3, 289–297.
  • Rawal, R.; Murugesan, V.; Katti, S. Structure-Activity Relationship Studies on Clinically Relevant HIV-1 NNRTIs. Curr. Med. Chem. 2012, 19, 5364–5380. DOI: 10.2174/092986712803833326.
  • Herdeiro, M. T.; Soares, S.; Silva, T.; Roque, F.; Figueiras, A. Impact of Rosiglitazone Safety Alerts on Oral Antidiabetic Sales Trends: A Countrywide Study in Portugal. Fundam. Clin. Pharmacol. 2016, 30, 440–449. DOI: 10.1111/fcp.12207.
  • Séïde, M.; Marion, M.; Mateescu, M. A.; Averill-Bates, D. A. The Fungicide Thiabendazole Causes Apoptosis in Rat Hepatocytes. Toxicol. In Vitro 2016, 32, 232–239. DOI: 10.1016/j.tiv.2015.12.018.
  • Rui, R.-M.; Tang, C.-R.; Zhang, C.-T.; Pan, W.-K.; Gan, K.; Luo, R.-H.; Wei, Z.-Q.; Jing, F.-S.; Huang, S.-M.; Yang, L.-M.; et al. C6-Structural Optimizations of 2-Aryl-1H-Pyrazole-S-Dabos: From anti-HIV to anti-DENV Activity. Bioorg. Chem. 2022, 119, 105494. DOI: 10.1016/j.bioorg.2021.105494.
  • Messore, A.; Corona, A.; Madia, V. N.; Saccoliti, F.; Tudino, V.; De Leo, A.; Scipione, L.; De Vita, D.; Amendola, G.; Di Maro, S.; et al. Pyrrolyl Pyrazoles as Non-Diketo Acid Inhibitors of the HIV-1 Ribonuclease H Function of Reverse Transcriptase. ACS Med. Chem. Lett. 2020, 11, 798–805. DOI: 10.1021/acsmedchemlett.9b00617.
  • Hassan, G. S.; Rahman, D. E. A.; Abdelmajeed, E. A.; Refaey, R. H.; Salem, M. A.; Nissan, Y. M. New Pyrazole Derivatives: Synthesis, anti-Inflammatory Activity, Cycloxygenase Inhibition Assay and Evaluation of Mpges. Eur. J. Med. Chem. 2019, 171, 332–342. DOI: 10.1016/j.ejmech.2019.03.052.
  • Nayak, S. G.; Poojary, B.; Kamat, V. Novel Pyrazole‐Clubbed Thiophene Derivatives via Gewald Synthesis as Antibacterial and anti‐Inflammatory Agents. Arch. Pharm. 2020, 353, 2000103. DOI: 10.1002/ardp.202000103.
  • Yang, Z.; Li, P.; Gan, X. Novel Pyrazole-Hydrazone Derivatives Containing an Isoxazole Moiety: Design, Synthesis, and Antiviral Activity. Molecules 2018, 23, 1798–1809. DOI: 10.3390/molecules23071798.
  • Ansari, A.; Ali, A.; Asif, M.; Shamsuzzaman, S. Microwave-Assisted Mgo NP Catalyzed One-Pot Multicomponent Synthesis of Polysubstituted Steroidal Pyridines. New J. Chem. 2018, 42, 184–197. DOI: 10.1039/C7NJ03742B.
  • Bekhit, A. A.; Saudi, M. N.; Hassan, A. M.; Fahmy, S. M.; Ibrahim, T. M.; Ghareeb, D.; El-Seidy, A. M.; Nasralla, S. N.; Bekhit, A. E. D. A. Synthesis, in Silico Experiments and Biological Evaluation of 1,3,4-trisubstituted pyrazole derivatives as antimalarial agents . Eur. J. Med. Chem. 2019, 163, 353–366. DOI: 10.1016/j.ejmech.2018.11.067.
  • Kumar, G.; Tanwar, O.; Kumar, J.; Akhter, M.; Sharma, S.; Pillai, C. R.; Alam, M. M.; Zama, M. S. Pyrazole-Pyrazoline as Promising Novel Antimalarial Agents: A Mechanistic Study. Eur. J. Med. Chem. 2018, 149, 139–147. DOI: 10.1016/j.ejmech.2018.01.082.
  • Liu, C. Y.; Jiang, X. X.; Zhu, Y. H.; Wei, D. N. Metabotropic Glutamate Receptor 5 Antagonist 2-Methyl-6-(Phenylethynyl)Pyridine Produces Antidepressant Effects in Rats: Role of Brain-Derived Neurotrophic Factor. Neuroscience 2012, 223, 219–224. DOI: 10.1016/j.neuroscience.2012.08.010.
  • Singh, K.; Pal, R.; Khan, S. A.; Kumar, B.; Akhtar, M. J. Insights into the Structure Activity Relationship of Nitrogen-Containing Heterocyclics for the Development of Antidepressant Compounds: An Updated Review. J. Mol. Struct. 2021, 1237, 130369. DOI: 10.1016/j.molstruc.2021.130369.
  • Desai, N. C.; Bhatt, K.; Jadeja, D. J.; Mehta, H. K.; Khedkar, V. M.; Sarkar, D. Conventional and Microwave‐Assisted Organic Synthesis of Novel Antimycobacterial Agents Bearing Furan and Pyridine Hybrids. Drug. Dev. Res. 2022, 83, 416–431. DOI: 10.1002/ddr.21872.
  • Desai, N. C.; Trivedi, A.; Somani, H.; Jadeja, K. A.; Vaja, D.; Nawale, L.; Khedkar, V. M.; Sarkar, D. Synthesis, Biological Evaluation, and Molecular Docking Study of Pyridine Clubbed 1,3,4-Oxadiazoles as Potential Antituberculars. Synth. Commun. 2018, 48, 524–540. DOI: 10.1080/00397911.2017.1410892.
  • Helal, M. H.; El-Awdan, S. A.; Salem, M. A.; Abd-Elaziz, T. A.; Moahamed, Y. A.; El-Sherif, A. A.; Mohamed, G. A. M. Synthesis, Biological Evaluation and Molecular Modeling of Novel Series of Pyridine Derivatives as Anticancer, anti-Inflammatory and Analgesic Agents. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2015, 135, 764–773. DOI: 10.1016/j.saa.2014.06.145.
  • Ibrahim, H. M.; Behbehani, H. The First Q-Tube Based High-Pressure Synthesis of anti-Cancer Active Thiazolo [4, 5-C] Pyridazines via the [4 + 2] Cyclocondensation of 3-Oxo-2-Arylhydrazonopropanals with 4-Thiazolidinones. Sci. Rep. 2020, 10, 1–15. DOI: 10.1038/s41598-020-63453-2.
  • Cihan-Üstündağ, G.; Şatana, D.; Özhan, G.; Çapan, G. Indole-Based Hydrazide-Hydrazones and 4-Thiazolidinones: Synthesis and Evaluation as Antitubercular and Anticancer Agents. J. Enzyme Inhib. Med. Chem. 2016, 31, 369–380. DOI: 10.3109/14756366.2015.1024673.
  • Hebishy, A. M.; Abdelfattah, M. S.; Elmorsy, A.; Elwahy, A. H. Novel Bis (Thiazolidin-4-Ones) Linked to Aliphatic or Aromatic Spacers: Synthesis, Characterization, and Anticancer Evaluation. J. Sulfur Chem. 2021, 42, 149–166. DOI: 10.1080/17415993.2020.1823978.
  • Desai, N. C.; Jadeja, K. A.; Jadeja, D. J.; Khedkar, V. M.; Jha, P. C. Design, Synthesis, Antimicrobial Evaluation, and Molecular Docking Study af Some 4-Thiazolidinone Derivatives Containing Pyridine and Quinazoline Moiety. Synth. Commun. 2020, 51, 1–963. DOI: 10.1080/00397911.2020.1861302.
  • Desai, N. C.; Joshi, V. V.; Rajpara, K. M.; Makwana, A. H. A New Synthetic Approach and in Vitro Antimicrobial Evaluation af Novel Imidazole Incorporated 4-Thiazolidinone Motifs. Arab. J. Chem. 2017, 10, S589–S599. DOI: 10.1016/j.arabjc.2012.10.020.
  • Desai, N. C.; Rupala, Y. M.; Khasiya, A. G.; Shah, K. N.; Pandit, U. P.; Khedkar, V. M. Synthesis, Biological Evaluation, and Molecular Docking Study of Thiophene‐, Piperazine‐, and Thiazolidinone‐Based Hybrids as Potential Antimicrobial Agents. J. Heterocycl. Chem. 2022, 59, 75–87. DOI: 10.1002/jhet.4366.
  • Subhedar, D. D.; Shaikh, M. H.; Khan, F. A. K.; Sangshetti, J. N.; Khedkar, V. M.; Shingate, B. B. Facile Synthesis of New N-Sulfonamidyl-4-Thiazolidinone Derivatives and Their Biological Evaluation. New J. Chem. 2016, 40, 3047–3058. DOI: 10.1039/C6NJ00021E.
  • Djukic, M.; Fesatidou, M.; Xenikakis, I.; Geronikaki, A.; Angelova, V. T.; Savic, V.; Pasic, M.; Krilovic, B.; Djukic, D.; Gobeljic, B.; et al. In Vitro Antioxidant Activity of Thiazolidinone Derivatives of 1,3-thiazole and 1,3,4-thiadiazole . Chem. Biol. Interact. 2018, 286, 119–131. DOI: 10.1016/j.cbi.2018.03.013.
  • Cihan-Üstündağ, G.; Gürsoy, E.; Naesens, L.; Ulusoy-Güzeldemirci, N.; Çapan, G. Synthesis and Antiviral Properties of Novel Indole-Based Thiosemicarbazides and 4-Thiazolidinones. Bioorg. Med. Chem. 2016, 24, 240–246. DOI: 10.1016/j.bmc.2015.12.008.
  • Barbosa, V. A.; Baréa, P.; Mazia, R. S.; Ueda-Nakamura, T.; da Costa, W. F.; Foglio, M. A.; Goes Ruiz, A. L. T.; de Carvalho, J. E.; Vendramini–Costa, D. B.; Nakamura, C. V.; Sarragiotto, M. H. Synthesis and Evaluation of Novel Hybrids Β-Carboline-4-Thiazolidinones as Potential Antitumor and Antiviral Agents. Eur. J. Med. Chem. 2016, 124, 1093–1104. DOI: 10.1016/j.ejmech.2016.10.018.
  • War, J. A.; Srivastava, S. K.; Srivastava, S. D. Design, Synthesis and DNA-Binding Study of Some Novel Morpholine Linked Thiazolidinone Derivatives. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2017, 173, 270–278. DOI: 10.1016/j.saa.2016.07.054.
  • Shoichet, B. K.; McGovern, S. L.; Wei, B.; Irwin, J. J. Lead Discovery Using Molecular Docking. Curr. Opin. Chem. Biol. 2002, 6, 439–446. DOI: 10.1016/S1367-5931(02)00339-3.
  • Friesner, R. A.; Murphy, R. B.; Repasky, M. P.; Frye, L. L.; Greenwood, J. R.; Halgren, T. A.; Sanschagrin, P. C.; Mainz, D. T. Extra Precision Glide: Docking and Scoring Incorporating a Model of Hydrophobic Enclosure for protein-ligand complexes. J. Med. Chem. 2006, 49, 6177–6196. DOI: 10.1021/jm051256o.
  • Halgren, T. A.; Murphy, R. B.; Friesner, R. A.; Beard, H. S.; Frye, L. L.; Pollard, W. T.; Banks, J. L. Glide: A New Approach for Rapid, Accurate Docking and Scoring. 2. Enrichment Factors in Database Screening. J. Med. Chem. 2004, 47, 1750–1759. DOI: 10.1021/jm030644s.
  • Friesner, R. A.; Banks, J. L.; Murphy, R. B.; Halgren, T. A.; Klicic, J. J.; Mainz, D. T.; Repasky, M. T.; Knoll, E. H.; Shelley, M.; Perry, J. K.; et al. Glide: A New Approach for Rapid, Accurate Docking and Scoring. 1. Method and Assessment of Docking Accuracy. J. Med. Chem. 2004, 47, 1739–1749. DOI: 10.1021/jm0306430.
  • Collin, F.; Karkare, S.; Maxwell, A. Exploiting Bacterial DNA Gyrase as a Drug Target: Current State and Perspectives. Appl. Microbiol. Biotechnol. 2011, 92, 479–497. DOI: 10.1007/s00253-011-3557-z.
  • Pommier, Y. Drugging Topoisomerases: Lessons and Challenges. ACS Chem. Biol. 2013, 8, 82–95. DOI: 10.1021/cb300648v.
  • Ehmann, D. E.; Lahiri, S. D. Novel Compounds Targeting Bacterial DNA Topoisomerase/DNA Gyrase. Curr. Opin. Pharmacol. 2014, 18, 76–83. DOI: 10.1016/j.coph.2014.09.007.
  • Halford, J. C.; Cooper, G. D.; Dovey, T. M.; Ishii, Y.; Rodgers, J.; Blundell, J. E. The Psychopharmacology of Appetite: Targets for Potential anti-Obesity Agents. Curr. Med. Chem.-Cent. Nerv. Syst. Agents. 2003, 3, 283–310. DOI: 10.2174/1568015033477695.
  • Desai, N.; Shihory, N.; Khasiya, A.; Pandit, U.; Khedkar, V. Quinazoline Clubbed Thiazole and 1, 3, 4-Oxadiazole Heterocycles: Synthesis, Characterization, Antibacterial Evaluation, and Molecular Docking Studies. Phosphorus Sulfur Silicon Relat. Elem. 2021, 196, 569–577. DOI: 10.1080/10426507.2021.1871732.
  • Desai, N. C.; Joshi, S. B.; Khedkar, V. M. Synthesis, Antimicrobial Activity and Molecular Docking of Pyrazole Bearing the Benzodiazepine Moiety. Anal. Chem. Lett. 2020, 10, 307–320. DOI: 10.1080/22297928.2020.1785325.
  • Schrödinger Release 2021-4: Maestro; Schrödinger, LLC, New York, 2021.

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