Main Article Content
Abstract
In present work, one-pot multicomponent reaction (MCR) route for the synthesis of benzylidene-iminothiazolyl- pyrazol-3-ol derivatives (5a-p) by reacting ethyl cyanoacetate (1), substituted benzaldehyde (2a-c), thiosemicarbazide (3) and substituted phenacyl bromide (4a-g). This reaction proceeds by using bleaching earth clay (BEC) (pH 12.5) in PEG-400 as a green reaction media. All the synthesized compounds were characterized by IR, 1H NMR, 13C NMR and mass spectral data. The pharmacological investigation of the synthesized compounds suggest that most of them showed good antioxidant activity.
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Copyright (c) 2021 Asian Journal of Organic & Medicinal Chemistry
This work is licensed under a Creative Commons Attribution 4.0 International License.
References
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References
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A.A. Bekhit, A. Hymete, A. Damtew, A.M.I. Mohamed and A.E.D.A. Bekhit, Synthesis and Biological Screening of Some Pyridine Derivatives as Anti-Malarial Agents, J. Enzyme Inhib. Med. Chem., 27, 69 (2012); https://doi.org/10.3109/14756366.2011.575071
A.A. Bekhit, H.M.A. Ashour, A.E.-D.A. Bekhit, H.M. Abdel-Rahman and S.A. Bekhit, Synthesis of Some Pyrazolyl Benzenesulfonamide Derivatives as Dual Anti-inflammatory Antimicrobial Agents, J. Enzyme Inhib. Med. Chem., 24, 296 (2009); https://doi.org/10.1080/14756360802188404
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M.L. Barreca, A. Chimirri, E. De Clercq, L. De Luca, A.-M. Monforte, P. Monforte, A. Rao and M. Zappalà, Anti-HIV agents: Design and Discovery of New Potent RT Inhibitors, Il Farmaco, 58, 259 (2003); https://doi.org/10.1016/S0014-827X(03)00024-7
H.A. Abdel-Aziz, B.F. Abdel-Wahab, M.A.M.Sh. El-Sharief and M.M. Abdulla, Synthesis and Anti-Arrhythmic Activity of Some Piperidine-Based 1,3-Thiazole, 1,3,4-Thiadiazole, and 1,3-Thiazolo[2,3-c]-1,2,4-Triazole Derivatives, Monatsh. Chem., 140, 431 (2009); https://doi.org/10.1007/s00706-008-0053-y
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S.K. Bharti, G. Nath, R. Tilak and S.K. Singh, Synthesis, Anti-Bacterial and Anti-Fungal Activities of Some Novel Schiff Bases Containing 2,4-Disubstituted Thiazole Ring, Eur. J. Med. Chem., 45, 651 (2010); https://doi.org/10.1016/j.ejmech.2009.11.008
A. Padmaja, C. Rajasekhar, A. Muralikrishna and V. Padmavathi, Synthesis and Antioxidant Activity of Oxazolyl/Thiazolylsulfonyl-methyl Pyrazoles and Isoxazoles, Eur. J. Med. Chem., 46, 5034 (2011); https://doi.org/10.1016/j.ejmech.2011.08.010
I. Lagoja, C. Pannecouque, G. Griffioen, S. Wera, V.M. Rojasdelaparra and A. Van Aerschot, Substituted 2-Aminothiazoles are Exceptional Inhibitors of Neuronal Degeneration in tau-Driven Models of Alzheimer's Disease, Eur. J. Pharm. Sci., 43, 386 (2011); https://doi.org/10.1016/j.ejps.2011.05.014
Y. Takahashi, M. Hashizume, K. Shin, T. Terauchi, K. Takeda, S. Hibi, K. Murata-Tai, M. Fujisawa, K. Shikata, R. Taguchi, M. Ino, H. Shibata and M. Yonaga, Design, Synthesis, and Structure–Activity Relation-ships of Novel Pyrazolo[5,1-b]thiazole Derivatives as Potent and Orally Active Corticotropin-Releasing Factor 1 Receptor Antagonists, J. Med. Chem., 55, 8450 (2012); https://doi.org/10.1021/jm300864p
B. Avila, A. Roth, H. Streets, D.S. Dwyer and M. Kurth, Triazolbenzo-[d]thiazoles: Efficient Synthesis and Biological Evaluation as Neuroprotective Agents, J. Bioorg. Med. Chem. Lett., 22, 5976 (2012); https://doi.org/10.1016/j.bmcl.2012.07.022
S.V. Andurkar, C. Béguin, J.P. Stables and H. Kohn, Synthesis and Structural Studies of Aza Analogues of Functionalized Amino Acids: New Anticonvulsant Agents, J. Med. Chem., 44, 1475 (2001); https://doi.org/10.1021/jm000517l
D. Havrylyuk, L. Mosula, B. Zimenkovsky, O. Vasylenko, A. Gzella and R. Lesyk, Synthesis and Anticancer Activity Evaluation of 4-Thiazolidinones Containing Benzothiazole Moiety, Eur. J. Med. Chem., 45, 5012 (2010); https://doi.org/10.1016/j.ejmech.2010.08.008
A.N. Ambhore, S.S. Kamble, S.N. Kadam, R.D. Kamble, M.J. Hebade, S.V. Hese, M.V. Gaikwad, R.J. Meshram, R.N. Gacche and B.S. Dawane, Design, Synthesis and in silico Study of Pyridine Based 1,3,4-Oxadiazole Embedded Hydrazinecarbothioamide Derivatives as Potent Anti-Tubercular Agent, Comput. Biol. Chem., 80, 54 (2019); https://doi.org/10.1016/j.compbiolchem.2019.03.002
A.N. Ambhore, V.D. Surywanshi, R.D. Kamble, S.V. Hese, P.P. Mogale, S.S. Kadam and B.S. Dawane, Synthesis and Biological Investigation of Isoxazolo[4,5-e][1,2,4]triazine Derivative, Der Pharma Chem., 7, 278 (2015).
P.P. Mogle, S.V. Hese, R.D. Kamble, M.J. Hebade, A.N. Ambhore, S.N. Kadam, S.S. Kadam, S.S. Kamble, R.N. Gacche and B.S. Dawane, Synthesis and Evaluation of 7,8,9,10-Tetrahydro-1H-pyrimido[1,2-a]- quinoline-2,5-dicarbonitrile Derivatives as Antimicrobial Agents, J. Chem. Pharm. Res., 7, 894 (2015).
P.D. Gavhane, S.N. Kadam, A.N. Ambhore and B.S. Dawane, Silica-Supported Sodium Carbonate: An Efficient Heterogeneous Catalyst for the Synthesis of New Thiazolopyrimidine Derivatives, Res. Chem. Int., 47, 3999 (2021); https://doi.org/10.1007/s11164-021-04508-5
S.N. Kadam, A.N. Ambhore, R.D. Kamble, M.G. Wakhradkar, P.D. Gavhane, M.V. Gaikwad, K.C. Gunturu and B.S. Dawane, Metal-free Efficient Thiolation of C(sp2) Functionalization via in situ-Generated NHTS for the Synthesis of Novel Sulfenylated 2-Aminothiazole and Imidazothiazole, New J. Chem., 45, 4632 (2021); https://doi.org/10.1039/D0NJ05904H
M.V. Gaikwad, R.D. Kamble, S.V. Hese, S.N. Kadam, A.N. Ambhore and B.S. Dawane, Synthesis of Pyrazolo[4,3-e]pyrimido[1,2-a]- pyrimidin-3-amine Derivatives and their Antimicrobial Activity, J. Chem. Pharm. Biol. Sci., 5, 376 (2017).
S.G. Alegaon, M.B. Hirpara, K.R. Alagawadi, K.K. Hullatti and K. Kashniyal, Synthesis of Novel Pyrazole-Thiadiazole Hybrid as Potential Potent and Selective Cyclooxygenase-2 (COX-2) Inhibitors, Bioorg. Med. Chem. Lett., 24, 5324 (2014); https://doi.org/10.1016/j.bmcl.2014.08.062
B. Bartolome, N. Nunez, M. Monagas and C. Gomez-Cordoves, In vitro Antioxidant Activity of Red Grape Skins, Eur. Food Res. Technol., 218, 173 (2004); https://doi.org/10.1007/s00217-003-0833-x
D.M. Dunlop, The Antihistamine Drugs, J. Pharmacol., 1, 1 (2011); https://doi.org/10.1111/j.2042-7158.1949.tb12365.x