Synthesis, Characterization and Biological Activity Evaluation of Some Pyrazoles, Thiazoles and Oxazoles Derived from 2-Mercaptoaniline
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Abstract
Synthesis of 2-mercaptobenzothiazole (A1) is performed from the reaction of o-aminothiophenol and carbon disulfide CS2 in ethanol under basic condition. Compound (A1) is reacted with chloro acetyl chloride to give compound (A2). Hydrazide acid compound (A3) is obtained from the reaction of compound (A2) with hydrazine hydrate in ethanol under reflux in the presence of glacial acetic acid .The reaction of hydrazide acid compound (A3) with ethyl acetoacetate gives pyrazole compound (A4). The new hydrazone compound (A5) was prepared from the reaction of compound (A3) with benzaldehyde. Reaction of compound (A3) with thiourea dissolved in ethanol gave 2-amino thiazole compounds(A6) which was used the reaction with 4–N,N-dimethyl benzaldehyde to yield compound hydrazone (A7).While, the reaction of compound (A2) with urea in the presence of ethanol gave 2-amino oxazole compounds (A8) which was used in the reaction with 3-hydroxy – 4 -methoxy benzaldehyde to yield hydrazone (A9). The structures of the prepared compounds were established by spectral (1H-NMR,Elemental analysis (C.H.N- ),and FT-IR. In addition to systematic characterization of some active functional groups in these compounds, antibacterial activity (Esheriechia coli, Bacillus subtilis ) for some of the synthesized compounds were evaluated against two types of fugal (Candida albicans ) , the synthesized compounds.
Received 2/9/2019
Accepted 18/5/2020
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Song P, Yu P, Lin J-S, Li Y, Yang N-Y, Liu X-Y. Transition-Metal-Free β-C–H Bond Carbonylation of Enamides or Amides with a Trifluoromethyl Group as CO Surrogate for the Synthesis of 1, 3-Oxazin-6-ones. Orglett. 2017;19(6):1330-3.
Manjula S, Noolvi NM, Parihar KV, Reddy SM, Ramani V, Gadad AK, et al. Synthesis and antitumor activity of optically active thiourea and their 2-aminobenzothiazole derivatives: A novel class of anticancer agents. Eur. J. Med. Chem. 2009;44(7):2923-9.
Sathe B, Jayachandran E, Jagtap V, Sreenivasa G. Anthelmintic activity of newly synthesized moieties of fluoro benzothiazole Schiff’s bases. Res J Pharm Biol Chem Sci. 2011;2(1):510-5.
Padmavathi V, Subbaiah DRCV, Mahesh K, Lakshmi TR. Synthesis and Bioassay of Amino-pyrazolone, Amino-isoxazolone and Amino-pyrimidinone Derivatives. Chem Pharm Bull. 2007;55(12):1704-9.
Siddiqui N, Rana A, Khan SA, Haque SE, Alam MS, Ahsan W, et al. Anticonvulsant and Toxicity Evaluation of Newly Synthesized 1-[2-(3, 4-disubstituted phenyl)-3-chloro-4-oxoazetidin-1-yl]-3-(6-substituted-1, 3-benzothiazol-2-yl) ureas. Acta Chim. Slov. 2009;56(2).
Song X, Vig BS, Lorenzi PL, Drach JC, Townsend LB, Amidon GL. Amino acid ester prodrugs of the antiviral agent 2-bromo-5, 6-dichloro-1-(β-D-ribofuranosyl) benzimidazole as potential substrates of hPEPT1 transporter. J Med Chem. 2005;48(4):1274-7.
Kumar D, Jacob MR, Reynolds MB, Kerwin SM. Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1. Bioorg Med Chem. 2002;10(12):3997-4004.
Panda SS, Ibrahim MA, Oliferenko AA, Asiri AM, Katritzky AR. Catalyst-free facile synthesis of 2-substituted benzothiazoles. Green chem. 2013;15(10):2709-12.
Sigmundová I, Zahradník P, Magdolen P, Bujdáková H. Synthesis and study of new antimicrobial benzothiazoles substituted on heterocyclic ring. Arkivoc. 2008;8:183-92.
Ren Y, Zhang L, Zhou C-H, Geng R-X. Recent development of benzotriazole-based medicinal drugs. Med chem. 2014;4(9):640-62.
Prabhu PP, Panneerselvam T, Shastry C, Sivakumar A, Pande SS. Synthesis and anticancer evaluation of 2-phenyl thiaolidinone substituted 2-phenyl benzothiazole-6-carboxylic acid derivatives. J Saudi Chem Soc. 2015;19(2):181-5.
Padalkar VS, Borse BN, Gupta VD, Phatangare KR, Patil VS, Umape PG, et al. Synthesis and antimicrobial activity of novel 2-substituted benzimidazole, benzoxazole and benzothiazole derivatives. Arabian J Chem. 2016;9:S1125-S30.
El-Damasy AK, Lee J-H, Seo SH, Cho N-C, Pae AN, Keum G. Design and synthesis of new potent anticancer benzothiazole amides and ureas featuring pyridylamide moiety and possessing dual B-RafV600E and C-Raf kinase inhibitory activities. Eur J Med Chem. 2016;115:201-16.
Kok SHL, Gambari R, Chui CH, Yuen MCW, Lin E, Wong RSM, et al. Synthesis and anti-cancer activity of benzothiazole containing phthalimide on human carcinoma cell lines. Bioorg Med Chem. 2008;16(7):3626-31.
Cressier D, Prouillac C, Hernandez P, Amourette C, Diserbo M, Lion C, et al. Synthesis, antioxidant properties and radioprotective effects of new benzothiazoles and thiadiazoles. Bioorg Med Chem. 2009;17(14):5275-84.
Bondock S, Fadaly W, Metwally MA. Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. Eur J Med Chem. 2010;45(9):3692-701.
Paramashivappa R, Kumar PP, Rao PS, Rao AS. Design, synthesis and biological evaluation of benzimidazole/benzothiazole and benzoxazole derivatives as cyclooxygenase inhibitors. Bioorg Med Chem. 2003;13(4):657-60.
Meltzer-Mats E, Babai-Shani G, Pasternak L, Uritsky N, Getter T, Viskind O, et al. Synthesis and mechanism of hypoglycemic activity of benzothiazole derivatives. J of med chem. 2013;56(13):5335-50.
Hettiarachchi C, Srikanth H, Karaiskaj D, Phan M-H. Perovskite Solar Absorbers and Ferroelectric Nanocomposites For Harvesting Solar Energy. 2015.
Franchini C, Muraglia M, Corbo F, Florio MA, Di Mola A, Rosato A, et al. Synthesis and Biological Evaluation of 2‐Mercapto‐1, 3‐benzothiazole Derivatives with Potential Antimicrobial Activity. Archiv der Pharmazie: IJlPMC. 2009;342(10):605-13.
Farhan MS, Saour KY. Synthesis of some Novel Nitrogenous Heterocyclic Compounds with Expected Biological Activity as Antimicrobial and Cytotoxic Agents. Iraqi J Pharm Sci. 2015;24(1):49-58.
Juber IK. Synthesis, Characterization and Biological Evaluation of Some 6-Methoxy-2-mercaptobenzimidazole Derivatives. Iraqi N J Chem. 2017; 17 (2):127- 139.
Sadek KU, Mekheimer RA, Abd-Elmonem M. Recent Developments in the Synthesis of Cinnoline Derivatives. Mini Rev Org Chem. 2019;16(6):578-88.
Al-Jumaili A, Alancherry S, Bazaka K, Jacob M. Review on the antimicrobial properties of carbon nanostructures. Materials. 2017;10(9):1066.