Main Article Content
Abstract
In this study, a series of new symmetrical N-carbothioamide substituted bispyrazolines (2a-f) had been systematically synthesized by using ring closure reactions of bischalcones (1a-f) with thiosemicarbazide under the alkaline-alcoholic conditions. The structures of bisheterocyclic products have been fully characterized on the basis of their IR, 1H & 13C NMR and ESI-MS spectral strategies. All the prepared compounds were also evaluated for their in vitro antimicrobial assay with the help of serial tube dilution procedure against the selected numbers of microbes (seven bacterial and five fungal strains). The most of the synthesized bisheterocycles exhibited noticeable antimicrobial potencies against the tested strains.
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Copyright (c) 2020 Asian Journal of Organic & Medicinal Chemistry
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References
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References
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T. Torroba, Poly-Sulfur-Nitrogen Heterocycles via Sulfur Chlorides and Nitrogen Reagents, J. Prakt. Chem., 341, 99 (1999); https://doi.org/10.1002/(SICI)1521-3897(199902)341:2<99::AID-PRAC99>3.0.CO;2-Z
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M. Garcia-Valverde and T. Torroba, Sulfur-Nitrogen Heterocycles, Molecules, 10, 318 (2005); https://doi.org/10.3390/10020318
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J. Alvarez-Builla, J.J. Vaquero and J. Barluenga, Modern Heterocyclic Chemistry, John Wiley & Sons, vol. 49, Set II (2011).
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J.M. López-Plá, A.K. Boudalis, J. Telser and R.G. Raptis, Chromium(III)-Pyrazole Complexes. X-Ray Crystal Structures, 1H NMR Investigation of Ligand Fluxional Behavior and EPR Studies, Inorg. Chim. Acta, 502, 119299 (2020); https://doi.org/10.1016/j.ica.2019.119299
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D. Havrylyuk, B. Zimenkovsky, O. Vasylenko and R. Lesyk, Synthesis and Anticancer and Antiviral Activities of New 2-Pyrazoline-Substituted 4-Thiazolidinones, J. Heterocycl. Chem., 50(S1), E55 (2013); https://doi.org/10.1002/jhet.1056
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Y.R. Prasad, A.L. Rao, L. Prasoona, K. Murali and P.R. Kumar, Synthesis and Antidepressant Activity of Some 1,3,5-triphenyl-2-pyraz-olines and 3-(2¢-Hydroxynaphthalen-1¢-yl)-1,5-diphenyl-2-pyrazolines, Bioorg. Med. Chem. Lett., 15, 5030 (2005); https://doi.org/10.1016/j.bmcl.2005.08.040
M. Amir, H. Kumar and S.A. Khan, Synthesis and Pharmacological Evaluation of Pyrazoline Derivatives as New Anti-inflammatory and Analgesic Agents, Bioorg. Med. Chem. Lett., 18, 918 (2008); https://doi.org/10.1016/j.bmcl.2007.12.043
D. Havrylyuk, B. Zimenkovsky, O. Vasylenko, A. Gzella and R. Lesyk, Synthesis of New 4-Thiazolidinone-, Pyrazoline- and Isatin-Based Conjugates with Promising Antitumor Activity, J. Med. Chem., 55, 8630 (2012); https://doi.org/10.1021/jm300789g
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Z. Ozdemir, H.B. Kandilci, B. Gumusel, U. Calis and A.A. Bilgin, Synthesis and Studies on Antidepressant and Anticonvulsant Activities of Some 3-(2-Furyl)pyrazoline Derivatives, Eur. J. Med. Chem., 42, 373 (2007); https://doi.org/10.1016/j.ejmech.2006.09.006
S.U.F. Rizvi, H.L. Siddiqui, M. Johns, M. Detorio and R.F. Schinazi, Anti-HIV-1 and Cytotoxicity Studies of Piperidyl-Thienyl Chalcones and their 2-Pyrazoline Derivatives, Med. Chem. Res., 21, 3741 (2012); https://doi.org/10.1007/s00044-011-9912-x
A.E.G.E. Amr, M. A. AL-OMAR and M. M. Abdalla, Anti-Inflammatory and Antipyretic Activities of Some Thiopyrimidine, Pyrazoline and Thiazolopyrimidine Derivatives, Lat. Am. J. Pharm., 35, 950 (2016).
Z. Brzozowski, S. Angielski and C. Wojcikowski, 2-Pyrazoline-1-carbox-amide Sulfonamide Derivatives useful as Hypoglycemic Agents, U.S. Patent 3,887,709 (1975).
O.D. Can, U.D. Ozkay, Z.A. Kaplancikli and Y. Ozturk, Effects of Some 1,3,5-Trisubstitued-2-pyrazoline Derivatives on Depression and Anxiety Parameters of Mice, Arch. Pharm. Res., 32, 1293 (2009); https://doi.org/10.1007/s12272-009-1915-5
M. Yusuf and I. Solanki, Synthesis and Antimicrobial Studies of Furyl Based New Bispyrazolines Linked via Aliphatic Chains, J. Saudi Chem. Soc., 21, 251 (2017); https://doi.org/10.1016/j.jscs.2015.02.002
M. Yusuf and M. Kaur, Synthesis and Antimicrobial Evaluations of New 5-aryl Linked Bispyrazolines, J. Heterocycl. Chem., 54, 735 (2017); https://doi.org/10.1002/jhet.2583
M. Yusuf and S. Thakur, Multicomponent Synthesis of New bis(Pyran-pyrazole) and their Antimicrobial-Antioxidant Evaluations, J. Serb. Chem. Soc., 84, 119 (2019); https://doi.org/10.2298/JSC171107074Y
M. Yusuf and S. Thakur, Synthesis and Applications of Bisheterocyclic Compounds, Curr. Org. Synth., 15, 603 (2018); https://doi.org/10.2174/1570179415666180405121737
M. Yusuf and P. Jain, Synthetic and Biological Studies of Pyrazolines and Related Heterocyclic Compounds, Arab. J. Chem., 7, 553 (2014); https://doi.org/10.1016/j.arabjc.2011.09.013
M. Yusuf, S. Nisa and K. Paul, New Biphenyl-Based Bispyrazolines: Synthesis, Antimicrobial and Docking Studies, J. Heterocycl. Chem., 56, 2659 (2019); https://doi.org/10.1002/jhet.3631
P.K. Sarvesh and K. Nizamuddin, Synthesis and Antimicrobial Study of Novel 1-Aryl-2-oxo-indano[3,2-d]pyrido/pyrimido[1,2-b]pyrimidines, Arch. Pharm. Chem. Life Sci., 341, 418 (2008); https://doi.org/10.1002/ardp.200700197