Silica catalyzed one pot synthesis of hybrid thiazolidin-4-one derivatives as anti-tubercular and anti-inflammatory agent by attenuating COX-2 pathway

References

• World Health Organisation. Antimicrobial Resistance: Global Report on Surveillance; WHO: Geneva, Switzerland, 2014.
   Google Scholar
• Dutt, A. K.; Stead, W. W. Epidemiology and Host Factors: Tuberculosis and Nontuberculous Mycobacterial Infection. 4th ed.; W.B. Saunders Company: Philadelphia, PA, 1999.
   Google Scholar
• Maher, D.; Floyd, K.; Raviglione, M. Strategic Framework to Decrease the Burden of TB/HIV Stop TB Department and Department of HIV/AIDS; World Health Organisation: Geneva, Switzerland, 2002. http://whqlibdoc.who.int/hq/2002/WHO_CDS_TB_2002.296.pdf.
   Google Scholar
• Dye, C. The TB Epidemic 2002–2020 (Abstract). Program of 4th World Congress Tuberculosis. Washington DC, 2002. Tuberculosis, 83, 1–3, 1–220.
   Google Scholar
• Rattan, A.; Kalia, A.; Ahmad, N. Multidrug-Resistant Mycobacterium Tuberculosis: Molecular Perspectives. Emerg. Infect. Dis. 1998, 4, 195. DOI: 10.3201/eid0402.980207.
   PubMed Web of Science ®Google Scholar
• Patel, H. M.; Noolvi, M. N.; Sethi, N. S. Synthesis and Antitubercular Evaluation of Imidazo[2,1-b][1,3,4]Thiadiazole Derivatives. Arab. J. Chem. 2017, 10, S996–S1002. DOI: 10.1016/j.arabjc.2013.01.001.
   Web of Science ®Google Scholar
• Campbell, P.; Banks, C. Reviews. Inflammation 2008, 454, 7203–7203.
   Google Scholar
• Kaufmann, S. H. E.; Dorhoi, A. Inflammation in Tuberculosis: Interactions, Imbalances and Interventions. Curr. Opin. Immunol. 2013, 25, 441–449. DOI: :. doi:10.1016/j.coi.2013.05.005. doi:DOI.
   PubMed Web of Science ®Google Scholar
• Cassano, P.; Lattanzi, L.; Soldani, F.; Navari, S.; Battistini, G.; Gemignani, A.; Cassano, G. B. Pramipexole in Treatment-Resistant Depression: An Extended Follow-up. Depress. Anxiety 2004, 20, 131–138. DOI: 10.1002/da.20038.
   PubMed Web of Science ®Google Scholar
• Sharma, P. C.; Sinhmar,A.; Sharma, A.; Rajak, H.; Pathak, D. P. Medicinal Significance of Benzothiazole Scaffold: An Insight View. J. Enzyme Inhib. Med. Chem. 2013, 28, 240–266. DOI: 10.3109/14756366.2012.720572.
   PubMed Web of Science ®Google Scholar
• Christian, N. Inflammation: Causes, Symptoms and Treatment. Medical News Today, November 24, 2017, pp 12. www.medicalnewstoday.%0Acom/articles/248423.php.
   Google Scholar
• Rostom, A.; Dube, C.; Wells, G. A.; Tugwell, P.; Welch, V.; Jolicoeur, E.; McGowan, J.; Lanas, A. Prevention of NSAID-Induced Gastroduodenal Ulcers (Review). Cochrane Database Syst. Rev. 2002, 4, CD002296. DOI: 10.1002/14651858.CD002296.
   Google Scholar
• Lee, A.; Cooper, M. G.; Craig, J. C.; Knight, J. F.; Keneally, J. P. Effects of Nonsteroidal Anti-Inflammatory Drugs on Postoperative Renal Function in Adults with Normal Renal Function. Cochrane Database Syst. Rev. 2007. DOI: 10.1002/14651858.CD002765.pub2.
   Web of Science ®Google Scholar
• Ugwu, D. I.; Okoro, U. C.; Ukoha, P. O.; Gupta, A.; Okafor, S. N. Novel Anti-Inflammatory and Analgesic Agents: Synthesis, Molecular Docking and In Vivo Studies. J. Enzyme Inhib. Med. Chem. 2018, 33, 405–415. DOI: 10.1080/14756366.2018.1426573.
   PubMed Web of Science ®Google Scholar
• Caughey, G. E.; Roughead, E. E.; Pratt, N.; Killer, G.; Gilbert, A. L. Stroke Risk and NSAIDs: An Australian Population-Based Study. Med. J. Aust. 2011, 195, 525–529. DOI: 10.5694/mja11.10055.
   PubMed Web of Science ®Google Scholar
• Varas-Lorenzo, C.; Riera-Guardia, N.; Calingaert, B.; Castellsague, J.; Pariente, A.; Scotti, L.; Sturkenboom, M.; Perez-Gutthann, S. Stroke Risk and NSAIDs: A Systematic Review of Observational Studies. Pharmacoepidemiol. Drug Saf. 2011, 20, 12225–12236. DOI: 10.1002/pds.2227.
   Web of Science ®Google Scholar
• Badr, S. M.; Barwa, R. M. Synthesis of Some New [1,2,4]Triazolo[3,4-b][1,3,4]Thiadiazines and [1,2,4]Triazolo[3,4-b][1,3,4] Thiadiazoles Starting from 5-Nitro-2-Furoic Acid and Evaluation of Their Antimicrobial Activity. Bioorg. Med. Chem. 2011, 19, 4506–4512. DOI: 10.1016/j.bmc.2011.06.024.
   PubMed Web of Science ®Google Scholar
• Miyahara, M.; Nakadate, M.; Sueyoshi, S.; Tanno, M.; Miyahara, M.; Kamiya, S. Antitumor Activity of 2-Acylamino-1,3,4-Thiadiazoles and Related Compounds. Chem. Pharm. Bull. 1982, 30, 4402–4406. DOI: 10.1248/cpb.30.4402.
   PubMed Web of Science ®Google Scholar
• Chen, Z.; Xu, W.; Liu, K.; Yang, S.; Fan, H.; Bhadury, P. S.; Huang, D.-Y.; Zhang, Y. Synthesis and Antiviral Activity of 5-(4-Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides. Molecules 2010, 15, 9046. DOI: 10.3390/molecules15129046.
   PubMed Web of Science ®Google Scholar
• Al‐Masoudi, N. A.; Al‐Soud, Y. A.; Al‐Masoudi, W. A. Thiosugar Nucleosides. Synthesis and Biological Activity of 1,3,4-Thiadiazole, Thiazoline and Thiourea Derivatives of 5-thio-D-Glucose. Nucleos. Nucleot. Nucl Acids. 2004, 23, 1739–1749. DOI: 10.1081/NCN-200034040.
   PubMed Web of Science ®Google Scholar
• Maddila, S.; Lavanya, P.; Jonnalagadda, S. B. Synthesis and Antimicrobial Studies of Novel (2-Benzylidene)-Phenylureido-Thiazolopyrimidine Derivatives. Chemija 2012, 23, 124–130.
   Web of Science ®Google Scholar
• Maddila, S.; Jonnalagadda, S. B. New Class of Triazole Derivatives and Their Antimicrobial Activity. Lett. Drug Des. Discov. 2012, 9, 687–693. DOI: 10.2174/157018012801319526.
   Web of Science ®Google Scholar
• Santhosh, K. G.; Poornachandra, Y.; Ratnakar, R. K.; Ganesh Kumar, C.; Narsaiah, B.. Synthesis of Novel Triazolothione, Thiadiazole, Triazole-Functionalized Furo/Thieno[2,3-b]Pyridine Derivatives and Their Antimicrobial Activity. Synth. Commun. 2017, 47, 1864–1873. DOI: 10.1080/00397911.2017.1354379.
   Web of Science ®Google Scholar
• Khan, I.; Ali, S.; Hameed, S.; Rama, N. H.; Hussain, M. T.; Wadood, A.; Uddin, R.; Ul-Haq, A.; Khan, A.; Ali, S.; Choudhary, I. Synthesis, Antioxidant Activities and Urease Inhibition of Some New 1,2,4-Triazole and 1,3,4-Thiadiazole Derivatives. Eur. J. Med. Chem. 2010. DOI: 10.1016/j.ejmech.2010.08.034.
   Web of Science ®Google Scholar
• Invidiata, F. P.; Simoni, D.; Scintu, F.; Pinna, N. 3,6-Disubstituted 1,2,4-Triazolo[3,4-b][1,3,4]Thiadiazoles: Synthesis, Antimicrobial and Antiviral Activity. II. Farmaco 1996, 51, 659–664.
   PubMedGoogle Scholar
• Gadad, A. K.; Palkar, M. B.; Anand, K.; Noolvi, M. N.; Boreddy, T. S.; Wagwade, J. Synthesis and Biological Evaluation of 2-Trifluoromethyl/Sulfonamido-5,6-Diaryl Substituted Imidazo[2,1-b]-1,3,4-Thiadiazoles: A Novel Class of Cyclooxygenase-2 Inhibitors. Bioorganic Med. Chem. 2008, 16, 276–283. DOI: 10.1016/j.bmc.2007.09.038.
   PubMed Web of Science ®Google Scholar
• Stillings, M. R.; Welbourn, A. P.; Walter, D. S. Substituted 1,3,4-Thiadiazoles with Anticonvulsant Activity. 2. Aminoalkyl Derivatives. J. Med. Chem. 1986, 29, 2280–2284. DOI: 10.1021/jm00161a025.
   PubMed Web of Science ®Google Scholar
• Rostom, S. A. F.; El-Ashmawy, I. M.; Abd El Razik, H. A.; et al. Design and Synthesis of Some Thiazolyl and Thiadiazolyl Derivatives of Antipyrine as Potential Non-Acidic Anti-Inflammatory, Analgesic and Antimicrobial Agents. Bioorg. Med. Chem. 2009, 17, 882–889. DOI: 10.1016/j.bmc.2008.11.035.
   PubMed Web of Science ®Google Scholar
• Petersen, K. F.; Krssak, M.; Inzucchi, S.; Cline, G. W.; Dufour, S.; Shulman, G. I. Mechanism of Troglitazone Action in Type 2 Diabetes. Diabetes 2000, 49, 827–831. DOI: 10.2337/diabetes.49.5.827.
   PubMed Web of Science ®Google Scholar
• Plutzky, J. The Potential Role of Peroxisome Proliferator-Activated Receptors on Inflammation in Type 2 Diabetes Mellitus and Atherosclerosis. Am. J. Cardiol. 2003, 92, 34–41. DOI: 10.1016/S0002-9149(03)00614-3.
   Web of Science ®Google Scholar
• Willson, T. M.; Wahli, W. Peroxisome Proliferator-Activated Receptor Agonists. Curr. Opin. Chem. Biol. 1997, 1, 235–241. DOI: 10.1016/S1367-5931(97)80015-4.
   PubMed Web of Science ®Google Scholar
• Baselga, J.; Mendelsohn, J. Status of Epidermal Growth Factor Receptor Antagonists in the Biology and Treatment of Cancer. J. Clin. Oncol. 2003, 21, 2787. DOI: 10.1200/JCO.2003.01.504.
   PubMed Web of Science ®Google Scholar
• Dömling, A.; Ugi, I. Multicomponent Reactions with Isocyanides. Angew. Chem. Int. Ed. Engl. 2000, 39, 3168–3210. DOI: 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U.
   PubMed Web of Science ®Google Scholar
• Bienayme, H.; Hulme, C.; Oddon, G. Maximizing Synthetic Efficiency: Multi-Component Transformations Lead the Way. Chem. Eur. J. 2000, 6, 3321–3329. DOI: 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO;2-A.
   PubMed Web of Science ®Google Scholar
• Orru, R. V. A.; Greef, M. d. Recent Advances in Solution-Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds. Synthesis 2003, 10, 1471–1499. DOI: 10.1055/s-2003-40507.
   Web of Science ®Google Scholar
• Datar, P. A.; Deokule, T. A. Design and Synthesis of Thiadiazole Derivatives as Antidiabetic Agents. Med. Chem. 2014, 4, 390–399.
   Google Scholar
• Lipinski, C. A. Lead- and Drug-like Compounds: The Rule-of-Five Revolution. Drug Discov. Today Technol. 2004, 1, 337–341. DOI: 10.1016/j.ddtec.2004.11.007.
   PubMedGoogle Scholar
• Leite, C. Q. F.; Beretta, A. L. R. Z.; Anno, I. S.; Telles, M. A. d S. Standartization of Broth Microdilution Method for Mycobacterium Tuberculosis. Mem. Inst. Oswaldo Cruz. 2000, 95, 127–129. DOI: 10.1590/S0074-02762000000100021.
   PubMed Web of Science ®Google Scholar
• Bari, S. B.; Firake, S. D. Exploring Anti-Inflammatory Potential of Thiazolidinone Derivatives of Benzenesulfonamide via Synthesis, Molecular Docking and Biological Evaluation. Antiinflamm Antiallergy Agents Med. Chem. 2016, 15, 44–53. DOI: 10.2174/1871523015666160524141630.
   PubMedGoogle Scholar
• Winter, C. A.; Risley, E. A.; Nuss, G. W. Carrageenin-Induced Edema in Hind Paw of the Rat as an Assay for Antiinflammatory Drugs. Exp. Biol. Med. 2013, 111, 544–547.
   Google Scholar
• Cresset, Flare software. Cresset: Cambridgeshire, UK, 2018. http://www.cresset-group.com/flare/.
   Google Scholar
• Marvin Sketch Group R, Marvin Sketch. Chemaxon: Budapest, Hungary, 2013. https://www.chemaxon.com/products/marvin/.
   Google Scholar
• Potemkin, V.; Grishina, M. Principles for 3D/4D QSAR Classification of Drugs. Drug Discov. Today 2008, 13, 952–959. DOI: 10.1016/j.drudis.2008.07.006.
   PubMed Web of Science ®Google Scholar
• Kumar, A.; Rajendran, V.; Singh, S. Antiplasmodial Activity of Hydroxyethylamine Analogs: Synthesis, Biological Activity and Structure Activity Relationship of Plasmepsin Inhibitors. Bioorg. Med. Chem. 2018, 26, 3837–3844. DOI: 10.1016/j.bmc.2018.06.037.
   PubMed Web of Science ®Google Scholar
• Potemkin, V.; Galimova, O.; Grishina, M. Cinderella’s Shoe for Virtual Drug Discovery Screening and Design. Drugs Future 2010, 35, 14–15.
   Google Scholar
• Potemkin, A.; Grishina, M.; Potemkin, V. Grid-Based Continual Analysis of Molecular Interior for Drug Discovery, QSAR and QSPR. Curr. Drug Discov. Technol. 2017, 14, 181–205.
   PubMedGoogle Scholar
• Potemkin, V.; Grishina, M. Grid-Based Technologies for in Silico Screening and Drug Design. Curr. Med. Chem. 2018, 25, 3526–3537. DOI: 10.2174/0929867325666180309112454.
   PubMed Web of Science ®Google Scholar
• Grishina, M.; Bolshakov, O.; Potemkin, A.; Potemkin, V. Theoretical Investigation of Electron Structure and Surface Morphology of Titanium Dioxide Anatase Nano-Particles. Comput. Theor. Chem. 2016, 1091, 122–136. DOI: 10.1016/j.comptc.2016.07.003.
   Web of Science ®Google Scholar
• Chemosophia. Chemosophia s.r.o., Prague, Czech Republic. http://www.chemosophia.com (accessed Dec 16, 2018).
   Google Scholar