Main Article Content
Abstract
A series of new thiophene tethered benzothiazepines (5a-h) were synthesized through citrus juice mediated (4+3) annulations of thienyl chalcones with 2-aminobenzenethiol in the presence of tetrabutylammonium bromide as phase transfer catalyst under reflux conditions. The synthesized compounds were characterized by spectroscopic and CHN analysis. To check the antioxidant potentials of the synthesized compounds, in vitro DPPH and hydroxyl radical scavenging assays were conducted. The results shows that amongst the series, compounds 5b with (21.44-49.72%) and (16.88-42.60%); 5c with (24.88-56.00%) and (22.33-53.12%); and 5h with (22.80-47.10%) and (15.33-44.12%) excellent DPPH and hydroxyl radical potencies comparable with the respective standards used in the experiments.
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Copyright (c) 2021 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
References
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- M.G. Prabhudeva, K. Kumara, A. Dileep Kumar, M.B. Ningappa, N.K. Lokanath and K. Ajay Kumar, Amberlyst-15 Catalyzed Synthesis of Novel Thiophene-Pyrazoline Derivatives: Spectral and Crystallographic Characterization and Anti-inflammatory and Antimicrobial Evaluation, Res. Chem. Intermed., 44, 6453 (2018); https://doi.org/10.1007/s11164-018-3501-2
- M.G. Prabhudeva, S. Bharath, A.D. Kumar, S. Naveen, N.K. Lokanath, B.N. Mylarappa and K.A. Kumar, Design and Environmentally Benign Synthesis of Novel Thiophene Appended Pyrazole Analogues as Anti-inflammatory and Radical Scavenging Agents: Crystallographic, in silico Modeling, Docking and SAR Characterization, Bioorg. Chem., 73, 109 (2017); https://doi.org/10.1016/j.bioorg.2017.06.004
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- N. Renuka, H.K. Vivek, G. Pavithra and K.A. Kumar, Synthesis of Coumarin Appended Pyrazolyl-1,3,4-oxadiazoles and Pyrazolyl-1,3,4-thiadiazoles: Evaluation of their in vitro Antimicrobial and Antioxidant Activities and Molecular Docking Studies, Russ. J. Bioorg. Chem., 43, 197 (2017); https://doi.org/10.1134/S106816201702011X
References
C.B.W. Phippen and C.S.P. McErlean, A 1,5-Benzothiazepine Synthesis, Tetrahedron Lett., 52, 1490 (2011); https://doi.org/10.1016/j.tetlet.2011.01.098
L. Fodor, J. Szabo, G. Bernath and P. Sohar, New Convenient Synthesis of 1,4-Benzothiazepines, Tetrahedron Lett., 36, 753 (1995); https://doi.org/10.1016/0040-4039(94)02359-J
K. Purandhar, M.A. Chari, P.P. Reddy, K. Mukkanti and G.M. Reddy, An Efficient One-pot Synthesis of Substituted 1,5-Benzoxazepines and 1,5-Benzothiazepines using Potassium Dodecatungstocobaltate Trihydrate (PDTC, K5CoW12O40·3H2O) as Heterogeneous Catalyst, Lett. Org. Chem., 11, 81 (2014); https://doi.org/10.2174/1570178610999131231123427
S. Preet and D.S. Cannoo, Synthesis and Characterization of Thiazepine/Benzothiazepine Derivatives through Intramolecular C-2 Ring Expansion Pathway, J. Chin. Chem. Soc., 64, 296 (2017); https://doi.org/10.1002/jccs.201600778
C. Spitz, V. Reboul and P. Metzner, Cyclic Sulfenamide: Versatile Template for the Synthesis of 1,4-Benzothiazepines, Tetrahedron Lett., 52, 6321 (2011); https://doi.org/10.1016/j.tetlet.2011.07.148
P. Zhang, L.Z. Wang, H.S. Wu, J.M. Lan, Y. Li and Y.X. Wang, The Synthesis and Biological Evaluation of a Series of Novel 2-COOC2H5/COONa Substituted 1,5-Benzothiazepine Derivatives as Antimicrobial Agents, Chin. Chem. Lett., 20, 660 (2009); https://doi.org/10.1016/j.cclet.2009.01.003
B.C. Manjunath, M. Manjula, K.R. Raghavendra, S. Shashikanth, K.A. Kumar and N.K. Lokanath, 2-(3,4-Dimethoxy phenyl)-4-(thiophen-2-yl)-2,3-dihydro-1,5-benzothiazepine, Acta Crystallogr. Sect. E Struct. Rep. Online, 70, o121 (2014); https://doi.org/10.1107/S1600536813034612
V.M. Berestovitskaya, R.I. Baichurin, N.I. Aboskalova and V.V. Gurzhiy, New Approaches to the Synthesis of 2,5-Dihydro- 1,5-benzothiazepines Containing Nitro Groups, Mend. Commun., 24, 380 (2014); https://doi.org/10.1016/j.mencom.2014.11.025
M. Manjula, B.C. Manjunath, N. Renuka, K.A. Kumar and N.K. Lokanath, 2-(4-Fluorophenyl)-4-(thiophen-2-yl)-2,3-dihydro-1,5-benzothiazepine, Acta Crystallogr. Sect. E Struct. Rep. Online, 69, o1608 (2013); https://doi.org/10.1107/S1600536813025889
F.L. Ansari, F. Iftikhar, Ihsan-ul-Haq, B. Mirza, M. Baseer and U. Rashid, Solid-Phase Synthesis and Biological Evaluation of a Parallel Library of 2,3-Dihydro-1,5-benzothiazepines, Bioorg. Med. Chem., 16, 7691 (2008); https://doi.org/10.1016/j.bmc.2008.07.009
L. Fodor, P. Csomos, T. Holczbauer, A. Kalman, A. Csampai and P. Sohar, Expected and Unexpected Reactions of 1,3-Benzothiazine Derivatives, I. Ring Transformation of b-Lactam Condensed 1,3-Benzothiazines into 4,5-Dihydro-1,4-benzothiazepines and Indolo-1,4-benzothiazepines, Tetrahedron Lett., 52, 224 (2011); https://doi.org/10.1016/j.tetlet.2010.10.160
T.A. Farghaly and H.M.E. Hassaneen, H-Ferrierite Zeolite: As an Effective and Reusable Heterogeneous Catalyst for Synthesis of 1,5-Benzothiazepine under Solvent Free Condition and 1,3-Dipolar Cycloaddition in Water, Arab. J. Chem., 10, S3255 (2017); https://doi.org/10.1016/j.arabjc.2013.12.024
R. Akbarzadeh, T. Amanpour, H.R. Khavasi and A. Bazgir, Atom Econo-mical Isocyanide-Based Multicomponent Synthesis of 2,5-Dioxopyrro-lidines, Spirobenzothiazinechromans and 1,5-Benzothiazepines, Tetrahedron, 70, 169 (2014); https://doi.org/10.1016/j.tet.2013.12.011
M. Incerti, D. Acquotti, P. Sandor and P. Vicini, Synthesis and NMR Spectral Assignments of Novel 1,4-Benzothiazepine-5-one Derivatives, Tetrahedron, 65, 7487 (2009); https://doi.org/10.1016/j.tet.2009.07.003
M. Mostofi, G. Mohammadi Ziarani and N. Lashgari, Design, Synthesis and Biological Evaluation of Benzofuran Appended Benzothiazepine Derivatives as Inhibitors of Butyrylcholinesterase and Antimicrobial Agents, Bioorg. Med. Chem., 26, 3076 (2018); https://doi.org/10.1016/j.bmc.2018.02.049
H. Kaur, S. Kumar, A. Chaudhary and A. Kumar, Synthesis and Biological Evaluation of Some New Substituted Benzoxazepine and Benzothiazepine as Antipsychotic as Well as Anticonvulsant Agents, Arab. J. Chem., 5, 271 (2012); https://doi.org/10.1016/j.arabjc.2010.09.011
A.K. Keshar, A. Tewari, S.S. Verma and S.K. Saraf, Novel Mannich-Bases as Potential Anticonvulsants: Syntheses, Characterization and Biological Evaluation, Cent. Nerv. Syst. Agents Med. Chem., 17, 219 (2017); https://doi.org/10.2174/1871524917666170717113524
M. Parthasarathy, C. Sureshkumar, S. Dhivya and S. Narasimhan, Virtual Screening and Evaluation of Heterocyclic 1, 5-Benzothiazepines Compounds Against MAP Kinase Protein, J. Pharm. Res., 6, 84 (2013); https://doi.org/10.1016/j.jopr.2012.11.018
S. Mor, P. Pahal and B. Narasimhan, Synthesis, Characterization, Biological Evaluation and QSAR Studies of 11-p-Substituted Phenyl-12-phenyl-11a,12-dihydro-11H-indeno[2,1-c][1,5]benzothiazepines as Potential Antimicrobial Agents, Eur. J. Med. Chem., 57, 196 (2012); https://doi.org/10.1016/j.ejmech.2012.09.003
L. Wang, P. Zhang, X. Zhang, Y. Zhang, Y. Li and Y. Wang, Synthesis and Biological Evaluation of a Novel Series of 1,5-Benzothiazepine Derivatives as Potential Antimicrobial Agents, Eur. J. Med. Chem., 44, 2815 (2009); https://doi.org/10.1016/j.ejmech.2008.12.021
Basavaraju, A.D. Kumar, N. Renuka, C.B. Vagish and K.A. Kumar, 1,4-Benzothiazepine Analogues: Synthesis, Characterization and Anti-microbial Evaluation, Der Pharma Chem., 9, 67 (2017).
K.R. Raghavendra, K. Ajay Kumar and S. Shashikanth, Synthesis of Novel 1,4-Benzothiazepines and in vitro Screening of their Antimicrobial Activity, Int. J. Pharm. Pharm. Sci., 6, 90 (2014).
N. Renuka, G. Pavithra and K.A. Kumar, Synthesis and their Antioxidant Activity Studies of 1,4-Benzothiazepine Analogues, Der Pharma. Chem., 6, 482 (2014).
N. Garg, T. Chandra, A.B. Archana, A.B. Jain and A. Kumar, Synthesis and Evaluation of Some New Substituted Benzothiazepine and Benzo-xazepine Derivatives as Anticonvulsant Agents, Eur. J. Med. Chem., 45, 1529 (2010); https://doi.org/10.1016/j.ejmech.2010.01.001
D.M. Lokeshwari, N.D. Rekha, B. Srinivasan, H.K. Vivek and A.K. Kariyappa, Design, Synthesis of Novel Furan Appended Benzothiazepine Derivatives and in vitro Biological Evaluation as Potent VRV-PL-8a and H+/K+ ATPase Inhibitors, Bioorg. Med. Chem. Lett., 27, 3048 (2017); https://doi.org/10.1016/j.bmcl.2017.05.059
V. Ambrogi, G. Grandolini, L. Perioli, L. Giusti, A. Lucacchini and C. Martini, Studies on Annulated 1,4-Benzothiazines and 1,5-benzothiaze-pines. IX. Imidazo[2,1-d][1,5] Benzothiazepines: Synthesis and in vitro Benzodiazepine Receptor Affinity, J. Med. Chem., 30, 429 (1995); https://doi.org/10.1016/0223-5234(96)88253-5
M. Hachida, H. Lu, N. Kaneko, Y. Horikawa, A. Ohkado, H. Gu, X.-L. Zhang, H. Hoshi, M. Nonoyama, H. Nakanishi and H. Koyanagi, Protective Effect of JTV519 (K201), A New 1,4-Benzothiazepine Derivative, On Prolonged Myocardial Preservation, Transplant. Proc., 31, 996 (1999); https://doi.org/10.1016/S0041-1345(98)01875-2
G. Grandolini, L. Perioli and V. Ambrogi, Synthesis of Some New 1,4-Benzothiazine and 1,5-Benzothiazepine Tricyclic Derivatives with Structural Analogy with TIBO and their Screening for Anti-HIV Activity, Eur. J. Med. Chem., 34, 701 (1999); https://doi.org/10.1016/S0223-5234(99)00223-8
M.G. Prabhudeva, K. Kumara, A. Dileep Kumar, M.B. Ningappa, N.K. Lokanath and K. Ajay Kumar, Amberlyst-15 Catalyzed Synthesis of Novel Thiophene-Pyrazoline Derivatives: Spectral and Crystallographic Characterization and Anti-inflammatory and Antimicrobial Evaluation, Res. Chem. Intermed., 44, 6453 (2018); https://doi.org/10.1007/s11164-018-3501-2
M.G. Prabhudeva, S. Bharath, A.D. Kumar, S. Naveen, N.K. Lokanath, B.N. Mylarappa and K.A. Kumar, Design and Environmentally Benign Synthesis of Novel Thiophene Appended Pyrazole Analogues as Anti-inflammatory and Radical Scavenging Agents: Crystallographic, in silico Modeling, Docking and SAR Characterization, Bioorg. Chem., 73, 109 (2017); https://doi.org/10.1016/j.bioorg.2017.06.004
D.K. Achutha, C.B. Vagish, N. Renuka, D.M. Lokeshwari and A.K. Kariyappa, Green Synthesis of Novel Pyrazoline Carbothioamides: A Potent Antimicrobial and Antioxidant Agents, Chem. Data Coll., 28, 100445 (2020); https://doi.org/10.1016/j.cdc.2020.100445
N. Renuka, H.K. Vivek, G. Pavithra and K.A. Kumar, Synthesis of Coumarin Appended Pyrazolyl-1,3,4-oxadiazoles and Pyrazolyl-1,3,4-thiadiazoles: Evaluation of their in vitro Antimicrobial and Antioxidant Activities and Molecular Docking Studies, Russ. J. Bioorg. Chem., 43, 197 (2017); https://doi.org/10.1134/S106816201702011X