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Abstract
In present work, ethyl 2-aminobenzo[d]thiazole-6-carboxylate was reacted to piperidine using copper(II) bromide to get ethyl 2-(piperidin-1-yl)benzo[d]thiazole-6-carboxylate. The reaction of ethyl 2-(piperidin-1-yl)benzo[d]thiazole-6-carboxylate with NaOH produces 2-(piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid. The inter-mediate 2-(piperidin-1-yl)benzo[d]thiazole-6-carboxylic acid have been isolated as stable compounds. The chemical structures of synthesized compounds were established based on the 1H & 13C NMR and IR spectral data. The mass of the novel compounds was established with the help of the LC-MS technique. The photoluminescence spectra explain the optical property of the compound. The biological studies of synthesized compounds show that the compound 5e possesses good antibacterial activity and compound 5d has good antifungal activity.
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References
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- M. Bratz, R. Kober, R. Seele, T. Saupe, N. Meyer, N. Walker, A. Landes, and H. Walter, A Novel One-pot Three-components Reaction: Synthesis of Indeno[2¢,1¢:5,6]pyrido[2,3:4¢¢,5¢¢]pyrimido[2¢¢,1¢¢-c]triazole-5,7-dione. A New Ring System, US Patent 20784767 (1993); Chem. Abstr., 120, 77293b (1994).
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- H.A. Parish Jr., R.D. Gilliom, W.P. Purcell, R.K. Browne, R.F. Spirk and H.D. White, Syntheses and Diuretic Activity of 1,2-Dihydro-2-(3-pyridyl)-3H-pyrido[2,3-d]pyrimidin-4-one and Related Compounds, J. Med. Chem., 25, 98 (1982); https://doi.org/10.1021/jm00343a022
- V.B. Birman and X. Li, Homobenzotetramisole: An Effective Catalyst for Kinetic Resolution of Aryl-Cycloalkanols, Org. Lett., 10, 1115 (2008); https://doi.org/10.1021/ol703119n
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References
S.E. O’Brien, H.L. Browne, T.D. Bradshaw, A.D. Westwell, M.F.G. Stevens and C.A. Laughton, Antitumor Benzothiazoles. Frontier Mole-cular Orbital Analysis Predicts Bioactivation of 2-(4-Aminophenyl)-benzothiazoles to Reactive Intermediates by Cytochrome P4501A1, Org. Biomol. Chem., 1, 493 (2003); https://doi.org/10.1039/b209067h
I. Yildiz-Oren, I. Yalcin, E. Aki-Sener and N. Ucarturk, Synthesis and Structure–Activity Relationships of New Antimicrobial Active Multi-substituted Benzazole Derivatives, Eur. J. Med. Chem., 39, 291 (2004); https://doi.org/10.1016/j.ejmech.2003.11.014
J.L. Jat, V.K. Salvi, G.L. Talesara and H. Joshi, Synthesis and Antimicrobial Evaluation of Some Pyrazolo-thiazolyl Alkoxy-1H-isoindole-1,3(2H)-dione Derivatives, J. Sulfur Chem., 27, 445 (2006); https://doi.org/10.1080/17415990600904697
C.S. Ra, B.Y. Jung and G. Park, The Fungicidal Benzothiazole Methoxyacrylates: Synthesis, Conformational Analysis and Fungicidal Activity, Heterocycl., 62, 793 (2004); https://doi.org/10.3987/COM-03-S(P)9
H. Bujdakova, T. Kuchta, S.A. Eva and A. Gvozdjakova, Anti-Candida Activity of Four Antifungal Benzothiazoles, FEMS Microbiol. Lett., 112, 329 (1993); https://doi.org/10.1111/j.1574-6968.1993.tb06471.x
R. Khurana, C. Coleman, C. Ionescu-Zanetti, S.A. Carter, V. Krishna, R.K. Grover, R. Roy and S. Singh, Mechanism of Thioflavin T Binding to Amyloid Fibrils, J. Struct. Biol., 151, 229 (2005); https://doi.org/10.1016/j.jsb.2005.06.006
Y. Heo, Y.S. Song, B.T. Kim and J.N. Heo, A Highly Regioselective Synthesis of 2-Aryl-6-chlorobenzothiazoles Employing Microwave-Promoted Suzuki-Miyaura Coupling Reaction, Tetrahedron Lett., 47, 3091 (2006); https://doi.org/10.1016/j.tetlet.2006.02.152
J. Das, R.V. Moquin, J. Lin, C. Liu, A.M. Doweyko, H.F. Defex, Q. Fang, S. Pang, S. Pitt, D.R. Shen, G.L. Schieven, J.C. Barrish and J. Wityak, Discovery of 2-Amino-heteroaryl-benzothiazole-6-anilides as Potent p56lck Inhibitors, Bioorg. Med. Chem., 13, 2587 (2003); https://doi.org/10.1016/S0960-894X(03)00511-0
S.R. Nagarajan, G.A. De Crescenzo, D.P. Getman, H.-F. Lu, J.A. Sikorski, J.L. Walker, J.J. McDonald, K.A. Houseman, G.P. Kocan, N. Kishore, P.P. Mehta, C.L. Funkes-Shippy and L. Blystone, Discovery of Novel Benzothiazolesulfonamides as Potent Inhibitors of HIV-1 Protease, Bioorg. Med. Chem., 11, 4769 (2003); https://doi.org/10.1016/j.bmc.2003.07.001
D. Cressier, C. Prouillac, P. Hernandez, C. Amourette, M. Diserbo, C. Lion and G. Rima, Synthesis, Antioxidant Properties and Radioprotective Effects of New Benzothiazoles and Thiadiazoles, Bioorg. Med. Chem., 17, 5275 (2009); https://doi.org/10.1016/j.bmc.2009.05.039
R.O. McCracken and K.B. Lipkowitz, Experimental and Theoretical Studies of Albendazole, Oxibendazole and Tioxidazole, J. Parasitol., 76, 180 (1990); https://doi.org/10.2307/3283011
R.O. McCracken and K.B. Lipkowitz, Structure-Activity Relationships of Benzothiazole and Benzimidazole Anthelmintics: A Molecular Modeling Approach to in vivo Drug Efficacy, J. Parasitol., 76, 853 (1990); https://doi.org/10.2307/3282805
M.Y. Yousef, A.M. Eisa, M.N. Nasra and S.A. El-Bialy, Synthesis of Certain Benzothiazole Derivatives to be Evaluated as Anthelminitcs, Mansoura J. Pharm. Sci., 13, 79 (1997).
F. Delmas, A. Avellaneda, C. Di Giorgio, M. Robin, E. De Clercq, P. Timon-David and J.-P. Galy, Synthesis and Antileishmanial Activity of (1,3-Benzothiazol-2-yl)amino-9-(10H)-acridinone Derivatives, Eur. J. Med. Chem., 39, 685 (2004); https://doi.org/10.1016/j.ejmech.2004.04.006
C. Pifl, L. Pichler, W. Kobinger and O. Hornykiewicz, The Dopamine Autoreceptor Agonist, B-HT 920, Preferentially Reduces Brain Dopamine Release in vivo: Biochemical Indices of Brain Dopamine, Noradrenaline and Serotonin in Ventriculocisternal Perfusates in the Cat, Eur. J. Pharmacol., 153, 33 (1988); https://doi.org/10.1016/0014-2999(88)90585-7
C.S. Schneider and J. Mierau, Dopamine Autoreceptor Agonists: Resolution and Pharmacological Activity of 2,6-Diaminotetrahydro-benzothiazole and an Aminothiazole Analog of Apomorphine, J. Med. Chem., 30, 494 (1987); https://doi.org/10.1021/jm00386a009
M. Mahran, S. William, F. Ramzy and A. Sembel, Synthesis and in vitro Evaluation of New Benzothiazole Derivatives as Schistosomicidal Agents, Molecules, 12, 622 (2007); https://doi.org/10.3390/12030622
B. Abdel-Wahab and S. Shaaban, Thiazolothiadiazoles and Thiazolo-oxadiazoles: Synthesis and Biological Applications, Synthesis, 46, 1709 (2014); https://doi.org/10.1055/s-0033-1338627
C. Praveen, A. Nandakumar, P. Dheenkumar, D. Muralidharan and P.T. Perumal, Microwave-Assisted One-pot Synthesis of Benzothiazole and Benzoxazole Libraries as Analgesic Agents, J. Chem. Sci., 124, 609 (2012); https://doi.org/10.1007/s12039-012-0251-3
J.C. Eriks, H. Van der Goot, G.J. Sterk and H. Timmerman, Histamine H2-Receptor Agonists. Synthesis, in vitro Pharmacology and Qualitative Structure-Activity Relationships of Substituted 4- and 5-(2-Aminoethyl)-thiazoles, J. Med. Chem., 35, 3239 (1992); https://doi.org/10.1021/jm00095a021
M. Bratz, R. Kober, R. Seele, T. Saupe, N. Meyer, N. Walker, A. Landes, and H. Walter, A Novel One-pot Three-components Reaction: Synthesis of Indeno[2¢,1¢:5,6]pyrido[2,3:4¢¢,5¢¢]pyrimido[2¢¢,1¢¢-c]triazole-5,7-dione. A New Ring System, US Patent 20784767 (1993); Chem. Abstr., 120, 77293b (1994).
M. Singh, S.K. Singh, M. Gangwar, G. Nath and S.K. Singh, Design, Synthesis and Mode of Action of Some Benzothiazole Derivatives Bearing an Amide Moiety as Antibacterial Agents, RSC Adv., 4,19013 (2014); https://doi.org/10.1039/C4RA02649G
J.M. Clark, S.J. Olsen, D.S. Weinberg, M. Dalvi, R.R. Whitney, D.P. Bonner and R.B. Sykes, in vivo Evaluation of Tigemonam, A Novel Oral Monobactam, Antimicrob. Agents Chemother., 31, 226 (1987); https://doi.org/10.1128/AAC.31.2.226
B.S. Hurlbert and B.F. Valenti, Condensed Pyrimidine Systems. XXIV. The Condensation of 2,4,6-triaminopyrimidine with Malondialdehyde Derivatives, J. Med. Chem., 11, 708 (1968); https://doi.org/10.1021/jm00310a016
H.A. Parish Jr., R.D. Gilliom, W.P. Purcell, R.K. Browne, R.F. Spirk and H.D. White, Syntheses and Diuretic Activity of 1,2-Dihydro-2-(3-pyridyl)-3H-pyrido[2,3-d]pyrimidin-4-one and Related Compounds, J. Med. Chem., 25, 98 (1982); https://doi.org/10.1021/jm00343a022
V.B. Birman and X. Li, Homobenzotetramisole: An Effective Catalyst for Kinetic Resolution of Aryl-Cycloalkanols, Org. Lett., 10, 1115 (2008); https://doi.org/10.1021/ol703119n
L. Fan, L. Wu and M. Ke, Synthesis of Novel Phenylazo-Substituted Salicylaldimine-Based Boron Difluoride Complexes, J. Chem. Res., 39, 442 (2015); https://doi.org/10.3184/174751915X14376642028953