Synthesis of Novel Pyrazolyl-1,3,4-Thiadiazole Analogues

References

• M. Li, and B. Zhao, “Progress of the Synthesis of Condensed Pyrazole Derivatives (from 2010 to Mid-2013),”European Journal of Medicinal Chemistry 85, (2014): 311–40.
   PubMed Web of Science ®Google Scholar
• A. Radwan, M. Khalid, H. Amer, and M. Alotaibi, “Anticancer and Molecular Docking Studies of Some New Pyrazole-1-Carbothioamide Nucleosides,” Biointerface Research in Applied Chemistry 9, (2019): 4642–8.
   Web of Science ®Google Scholar
• M. Ehab, A. E. Gedawy, A. M. Kassab, and K. El, “Design, Synthesis and Biological Evaluation of Novel Pyrazole Sulfonamide Derivatives as Dual COX-2/5-LOX Inhibitors,”European Journal of Medicinal Chemistry 189, (2020): 112066.
   PubMed Web of Science ®Google Scholar
• A. M. Vijesh, A. M. Isloor, P. Shetty, S. Sundershan, and H. K. Fun, “New Pyrazole Derivatives Containing 1,2,4-triazoles and Benzoxazoles as Potent Antimicrobial and Analgesic Agents,” European Journal of Medicinal Chemistry 62, (2013): 410–5.
   PubMed Web of Science ®Google Scholar
• R. Neidiane, P. R. Trindade, L. M. Lopes, J. O. Naves, P. H. Fajemiroye, N. O. Alves, L. M. Amaral, A. C. S. Liao, C. H. Rebelo, V. A. Castro, et al. “The Newly Synthesized Pyrazole Derivative 5-(1-(3 Fluorophenyl)-1H-Pyrazol-4-yl)-2H-Tetrazole Reduces Blood Pressure of Spontaneously Hypertensive Rats via NO/cGMO Pathway,” Frontiers in Physiology. 9, (2018): 1073–83.
   PubMed Web of Science ®Google Scholar
• D. C. Malvar, R. T. Ferreira, R. A. de Castro, L. L. de Castro, A. C. Freitas, E. A. Costa, I. F. Florentino, J. C. Mafra, G. E. de Souza, and F. A. Vanderlinde, “Antinociceptive, anti-Inflammatory and Antipyretic Effects of 1.5-Diphenyl-1H-Pyrazole-3-Carbohydrazide, a New Heterocyclic Pyrazole Derivative,”Life Sciences 95no. 2 (2014): 81–8.
   PubMed Web of Science ®Google Scholar
• G. M. Reddy, R. G. Jarem, V. Z. Grigory, S. Gundala, and N. B. Reddy, “Pyranopyrazoles as Efficient Antimicrobial Agents: Green, One Pot and Multicomponent Approach,” Bioorganic Chemistry 82, (2019): 324–31.
   PubMed Web of Science ®Google Scholar
• V. L. M. Silva, J. Elguero, and A. M. S. Silva, “Current Progress on Antioxidants Incorporating the Pyrazole Core,”European Journal of Medicinal Chemistry 156, (2018): 394–429.
   PubMed Web of Science ®Google Scholar
• A. Ansari, A. Ali, M. Asif, and S. Shamsuzzaman, “Biologically Active Pyrazole Derivatives,”New Journal of Chemistry 41no. 1 (2017): 16–41.
   Web of Science ®Google Scholar
• G. Satish, R. A. Srinivasa, L. P. Jeevan, R. V. Rajeswar, and P. Santhosh, “An Efficient Synthesis of Pyrazolyl‐1,2,3‐Thiadiazoles via Hurd–Mori Reaction,” Journal of Heterocyclic Chemistry 56, (2019): 2163–9.
   Web of Science ®Google Scholar
• G. Serban, O. Stanasel, E. Serban, and S. Bota, “ 2-Amino-1,3,4-thiadiazole as a potential scaffold for promising antimicrobial agents,”Drug Design, Development and Therapy 12, (2018): 1545–66.
   PubMed Web of Science ®Google Scholar
• G. Serban, “Synthetic Compounds with 2-Amino-1,3,4-Thiadiazole Moiety against Viral Infections,”Molecules 25no. 4 (2020): 942–64.
   PubMed Web of Science ®Google Scholar
• T. A. Farghaly, M. A. Abdallah, G. S. Masaret, and Z. A. Muhammad, “New and Efficient Approach for Synthesis of Novel bioactive [1,3,4]thiadiazoles incorporated with 1,3-thiazole moiety,”European Journal of Medicinal Chemistry 97, (2015): 320–33.
   PubMed Web of Science ®Google Scholar
• N. Chidananda, B. Poojary, V. Sumangala, N. S. Kumari, P. Shetty, and T. Arulmoli, “Facile Synthesis, Characterization and Pharmacological Activities of 3,6-Disubstituted 1,2,4-Triazolo[3,4-b][1,3,4]Thiadiazoles and 5,6-Dihydro-3,6-Disubstituted-1,2,4-Triazolo[3,4-b][1,3,4]Thiadiazoles,” European Journal of Medicinal Chemistry. 51, (2012): 124–36.
   PubMed Web of Science ®Google Scholar
• E. E. Oruc, S. Rollas, F. Kandemirli, N. Shvets, and A. S. Dimoglo, “1,3,4-thiadiazole Derivatives. Synthesis, Structure Elucidation, and Structure-Antituberculosis Activity Relationship Investigation,”Journal of Medicinal Chemistry 47, no. 27 (2004): 6760–7.
   PubMed Web of Science ®Google Scholar
• A. N. Y. Megally, and M. M. Kamel, “Synthesis and Anticancer Evaluation of 1,3,4-Oxadiazoles, 1,3,4-Thiadiazoles, 1,2,4-Triazoles and Mannich Bases,”Chemical & Pharmaceutical Bulletin 63, no. 5 (2015): 369–76.
   PubMed Web of Science ®Google Scholar
• (a) K. M. Dawood, and T. A. Farghaly, “Thiadiazole inhibitors: A patent review. Expert Opinion on Therapeutic Patents 27 (2017): 477–505. (b) G. Serban, “Future prospects in the treatment of parasitic diseases: 2-amino-1,3,4-thiadiazoles in leishmaniasis,” Molecules, 24 (2019): 1557.
   PubMed Web of Science ®Google Scholar
• (a) L. Brunton, B. Chabner, and B. G. Knollman, Goodman & Gilman's the Pharmacological Basis of Therapeutics (MacGraw-Hill: New York, NY, USA, 2010). (b) V. R. Pattabiraman, and J. W. Bode, “Rethinking amide bond synthesis,” Nature, 480 (2011): 471–479. (c) A. A. Kaspar, and J. M. Reichert, “Drug future directions for peptide therapeutics development,” Discovery Today, 18 (2013): 807–817. (d) D. G. Brown, and J. Bostrom, “Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone?” Journal of Medicinal Chemistry. 59 (2016): 4443–4458.
   Google Scholar
• O. Turan, E. Erdal, and M. Olcay, “Use of Lawesson’s Reagent in Organic Syntheses,” Chemical Reviews. 107, (2007): 5210–78.
   PubMed Web of Science ®Google Scholar
• A. A. Kiryanov, P. Sampson, and A. J. Seed, “Synthesis of 2-alkoxy-substituted thiophenes, 1,3-thiazoles, and related S-heterocycles via Lawesson's reagent-mediated cyclization under microwave irradiation: applications for liquid crystal synthesis,”The Journal of Organic Chemistry 66, no. 23 (2001): 7925–9.
   PubMed Web of Science ®Google Scholar
• E. Aparna, K. M. Lokanatha Rai, M. Sureshbabu, R. L. Jagadish, S. L. Gaonkar, and K. Byrappa, “Synthesis of Thioesters and Thioamides under Solvothermal Condition Using Thiourea as Thionating Agent,”Journal of Materials Science 41, no. 5 (2006): 1391–3.
   Web of Science ®Google Scholar
• A. B. Charette, and M. Grenon, “Mild Method for the Conversion of Amides to Thioamides,”The Journal of Organic Chemistry 68, no. 14 (2003): 5792–4.
   PubMed Web of Science ®Google Scholar
• R. Venkat Ragavan, V. Vijayakumar, and N. Suchetha Kumari, “Synthesis and Antimicrobial Activities of Novel 1,5-Diaryl Pyrazoles,”European Journal of Medicinal Chemistry 45, no. 3 (2010): 1173–80.
   PubMed Web of Science ®Google Scholar
• V. Ines, P. R. Andrea, M. M. Kata, B. Karmen, and B. Branimir, “Synthesis and Biological Validation of Novel Pyrazole Derivatives with Anticancer Activity Guided by 3D-QSAR Analysis,” Bioorganic and Medicinal Chemistry. 20, (2012): 2101–10.
   PubMed Web of Science ®Google Scholar
• N. P. Rai, V. K. Narayanaswamy, S. Shashikanth, and P. N. Arunachalam, “Synthesis, Characterization and Antibacterial Activity of 2-[1-(5-Chloro-2-Methoxy-Phenyl)-5-Methyl-1H-Pyrazol-4-yl]-5-(Substituted-Phenyl)-[1,3,4]Oxadiazoles,”European Journal of Medicinal Chemistry 44, no. 11 (2009): 4522–7.
   PubMed Web of Science ®Google Scholar
• A. A. Bekhit, H. M. A. Ashour, Y. S. A. Ghany, A. E. D. A. Bekhit, and A. Baraka, ” “Synthesis and Biological Evaluation of Some Thiazolyl and Thiadiazolyl Derivatives of 1H-Pyrazole as anti-Inflammatory Antimicrobial Agents,”European Journal of Medicinal Chemistry 43, no. 3 (2008): 456–63.
   PubMed Web of Science ®Google Scholar
• Rahmi Kasımoğulları, Metin Bülbül, B. Seçkin Arslan, and Başak Gökçe, “Seckin Arslan, B.; Basak G. “Synthesis, Characterization and Antiglaucoma Activity of Some Novel Pyrazole Derivatives of 5-Amino-1,3,4-Thiadiazole-2-Sulfonamide,”European Journal of Medicinal Chemistry 45, no. 11 (2010): 4769–73.
   PubMed Web of Science ®Google Scholar
• S. Ningaiah, U. K. Bhadraiah, S. Keshavamurthy, and C. Javarasetty, “Novel Pyrazoline Amidoxime and Their 1,2,4-oxadiazole analogues: synthesis and pharmacological screening,”Bioorganic & Medicinal Chemistry Letters 23, no. 16 (2013): 4532–8.
   PubMed Web of Science ®Google Scholar
• Bruker. APEX2 and SAINT. (Madison, Wisconsin, USA: Bruker AXS Inc., 2009).
   Google Scholar
• G. M. Sheldric, “A Short History of SHELX,” Acta Cryst A64, (2008): 112–22.
   Web of Science ®Google Scholar
• (a) Wagner, R. B.; Zook, H. D. Synthetic organic chemistry (John Willey & Sons, New York, 1953), 569. b) Yale, H. L.; Losee, K.; Martins, J.; Holsing, M.; Perry, F. M.; Bernstein, J. “Chemotherapy of Experimental Tuberculosis. VIII. The Synthesis of Acid Hydrazides, their Derivatives and Related Compounds,” Journal of the American Chemical Society 75, (1953): 1933–1942.
   Google Scholar
• For appropriate precautions when handling H2S, see: Prudent Practices in the Laboratory: Handling and Disposal of Chemicals (Washington, DC: National Research Council, National Academy Press, 1995), 342–343.
   Google Scholar
• K. B. Umesha, and K. M. L. Rai, “Synthesis and Antimicrobial Activity of Pyrazole Derivatives via 1, 3-Dipolar Cycloaddition of Nitrile Imines with Ethyl Acetoacetate,” Bulg. Chem. Commun 42, (2010): 11–5.
   Google Scholar
• A. L. Spek, “Structure Validation in Chemical Crystallography,”Acta Crystallographica. Section D, Biological Crystallography 65, no. Pt 2 (2009): 148–55.
   PubMedGoogle Scholar
• (a) CCDC 968764 for (4a) and CCDC 967458 for (7a) contain the supplementary crystallographic data for this paper. They can be obtained free of charge from The Cambrige Crystallographic Data Centere via www.ccdc.cam.ac.uk/data_request/cif. (b) Chandra, N. Srikantamurthy, Shamantha Kumar, B. H., Doreswamy K. B. Umesha, and M. Mahendra, “N’-Benzoyl-5-methyl-1,3-diphenyl-1H-pyrazole-4-carbohydrazide,” Acta Crystallogr E69 (2013): o1769. (c) Chandra, S. S., Mahesh, N. Srikantamurthy, K. B. Umesha, K. Palani, M. Mahendra, “5-Methyl-1,3-diphenyl-N-(5-phenyl-1,3,4-thiadiazol-2-yl)-1H-pyrazole-4-carboxamide,” Acta Crystallogr E69 (2013): o1736.
   Google Scholar
• P. C. Michel, and I. L. Matthew, “Thionation Reactions of Lawesson’s Reagents,” Tetrahedron 41, (1985): 5061–87.
   Web of Science ®Google Scholar