Copyright (c) 2023 J UDAYA BHASKAR
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Design, Synthesis, Structural Characterization and Antimicrobial Screening of Several Novel Benzothiophene Linked Thiazolidines
Corresponding Author(s) : J UDAYA BHASKAR
Asian Journal of Chemistry,
Vol. 35 No. 9 (2023): Vol 35 Issue 9, 2023
Abstract
A novel sequence of (19E)-(3-(benzo[b]thiophen-3-yl)-N′-((Z)-5-benzyliden-4-oxo-3-phenyl thiazolidin-2-ylidene)propanehydrazides (6a-f) was synthesized in moderate to good yields from the final intermediate, (E)-(3-(benzo[b]thiophen-3-yl)-N′-(4-oxo-3-phenylthiazolidin- 2-ylidene)propane hydrazide (5). In present work, 3-(benzo[b]thiophen-3-yl)propanoic acid (1) was selected as raw material and compounds such as 1-(benzo[b]thiophen-3-yl)pentan-3-one (2), 3-(benzo[b]thiophen-3-yl)propanehydrazide (3) and 1-(3-(benzo[b]- thiophen-3-yl)-propanoyl)-4-phenylsemicarbazide (4) were materialized as intermediates. All the isolated intermediates and target compounds have been characterized with the data obtained from different spectroscopic methods. The products were also examined against few microorganisms. According to the screening results, the tested targets performed satisfactory growth of inhibition.
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- D.R. Richardson, D.S. Kalinowski, S. Lau, P.J. Jansson and D.B. Lovejoy, Biochim. Biophys. Acta, 1790, 702 (2009); https://doi.org/10.1016/j.bbagen.2008.04.003
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References
D.R. Richardson, D.S. Kalinowski, S. Lau, P.J. Jansson and D.B. Lovejoy, Biochim. Biophys. Acta, 1790, 702 (2009); https://doi.org/10.1016/j.bbagen.2008.04.003
A.R. Kazemizadeh, N. Shajari, R. Shapouri, N. Adibpour and R. Teimuri-Mofrad, Iran. Chem. Soc., 13, 1349 (2016); https://doi.org/10.1007/s13738-016-0849-3
M.M.E. Shakdofa, M.H. Shtaiwi, N. Morsy and T.M.A. Abdel-Rassel, Main Group Chem., 13, 187 (2014); https://doi.org/10.3233/MGC-140133
J.C. Coa, W. Castrillon, W. Cardona, M. Carda, V. Ospina, J.A. Munoz, I.D. Velez and S.M. Robledo, Eur. J. Med. Chem., 101, 746 (2015); https://doi.org/10.1016/j.ejmech.2015.07.018
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R.B. Pathak, P.T. Chovatia and H.H. Parekh, Bioorg. Med. Chem. Lett., 22, 5129 (2012); https://doi.org/10.1016/j.bmcl.2012.05.063
I.I. Grynyuk, S.V. Prylutska, D.V. Franskevych, V.A. Trush, T.Y. Sliva, M.S. Slobodyanik, V.V. Hurmach, Y.I. Prylutskyy, O.P. Matyshevska and U. Ritter, Mater. Sci. Eng. Technol., 47, 98 (2016); https://doi.org/10.1002/mawe.201600471
Y. Pommier, Nat. Rev. Cancer, 6, 789 (2006); https://doi.org/10.1038/nrc1977
G. Edwards and A.H. Weston, Ann. Rev. Pharmacol. Toxicol., 33, 597 (1993); https://doi.org/10.1146/annurev.pa.33.040193.003121
R.J. Williams, J.P.E. Spencer and C. Rice-Evans, Free Radic. Biol. Med., 36, 838 (2004); https://doi.org/10.1016/j.freeradbiomed.2004.01.001
M.N. George, P. Horia, D. Constantin and M. Alexandru-Vasile, Farmacia, 58, 190 (2010).
T.R. Bosin and E.E. Campaigne, Adv. Drug Res., 11, 191 (1977).
J.D. Croxtall and G.L. Plosker, Drugs, 69, 339 (2009); https://doi.org/10.2165/00003495-200969030-00009
S. Pichard, A. Afenjar, O. Boespflug-Tanguy and C. Sarret, Neuropediatrics, 48, 205 (2017); https://doi.org/10.1055/s-0037-1601856
C.N. Meixner, M.W. Aref, A. Gupta, E.M.B. McNerny, D. Brown, J.M. Wallace and M.R. Allen, Calcif. Tissue Int., 101, 75 (2017); https://doi.org/10.1007/s00223-017-0257-4
L.L. Sun, C.L. Deng, R.Y. Tang and X.G. Zhang, J. Org. Chem., 76, 7546 (2011); https://doi.org/10.1021/jo201081v
T. Tomasic and L. Masic, Curr. Med. Chem., 16, 1596 (2009); https://doi.org/10.2174/092986709788186200
A.M.C. Andrade, W.T. Lima and M.P.A. Rocha, Boll. Chim. Farm., 141, 428 (2002).
T. Tomašic, N. Zidar, A. Kovaè, S. Turk, M. Simèiè, D. Blanot, M. Müller-Premru, M. Filipiè, S.G. Grdadolnik, A. Zega, M. Anderluh, S. Gobec, D. Kikelj and L. Peterlin-Mašiè, ChemMedChem, 5, 286 (2010); https://doi.org/10.1002/cmdc.200900449
M.S.A. El-Gaby, G.A.M. El-Hag Ali, A.A. El-Maghraby, M.T. Abd El-Rahman and M.H.M. Helal, Eur. J. Med. Chem., 44, 4148 (2009); https://doi.org/10.1016/j.ejmech.2009.05.005
A.A.R. Silva, A.J. Silva Góes, W.T. Lima and M.B. Souza Maia, Chem. Pharm. Bull., 51, 1351 (2003); https://doi.org/10.1248/cpb.51.1351
T. Tomasic and L.P. Masic, Curr. Top. Med. Chem., 14, 130 (2013); https://doi.org/10.2174/1568026613666131113153251
F.L. Gouveia, R.M.B. de Oliveira, T.B. de Oliveira, I.M. da Silva, S.C. do Nascimento, K.X.F.R. de Sena and J.F.C. de Albuquerque, Eur. J. Med. Chem., 44, 2038 (2009); https://doi.org/10.1016/j.ejmech.2008.10.006
R. Ottana, R. MacCari, M.L. Barreca, G. Bruno, A. Rotondo, A. Rossi, G. Chiricosta, R. Di Paola, L. Sautebin, S. Cuzzocrea and M.G. Vigorita, Bioorg. Med. Chem., 13, 4243 (2005); https://doi.org/10.1016/j.bmc.2005.04.058
P. Vicini, A. Geronikaki, K. Anastasia, M. Incerti and F. Zani, Bioorg. Med. Chem., 14, 3859 (2006); https://doi.org/10.1016/j.bmc.2006.01.043
S.R. Jain and A. Kar, Planta Med., 20, 118 (1971); https://doi.org/10.1055/s-0028-1099675