Synthesis of novel 2-amino-5-arylazothiazol derivatives and their biological impacts: Assessment of toxicity and antioxidant enzymes activities

Mohamed Ezzat Khalifa, Mahmoud Abdel-Halim Mohamed, Noura Homoud Alshehri

Abstract


The reactivity study of both the amino group and the aryl substituent of the newly synthesized 2-amino-5-(4-acetylphenylazo)-thiazole compound and its derivatives via various electrophilic reagents were performed to obtain the expected new bioactive chalcone, imine and pyrazole- thiazolidine derivatives. The synthesized compounds were chemically elucidated by analytical and spectral methods, and biologically evaluated upon screening in vitro and in vivo for their toxicity and antioxidant activity based on liver function enzymes.


Keywords


2-Aminothiazole, Chalcone, Imine, Pyrazole, Azo coupling, Biological activities.

Full Text:

PDF

References


REFERENCES

P.C. Hang, J.F. Honek, Electronic structure calculations on the thiazole-containing antibiotic thiostrepton: molecular mechanics, semi-empirical and ab initio analyses, Bioorg. Med. Chem. Lett., 15, 1471-1474 (2005).

A. Geronikaki, P. Vicini, N. Dabarakis, A. Lagunin, V. Poroikov, J. Dearden, H. Modarresi, M. Hewitt, G. Theophilidis, Evaluation of the local anaesthetic activity of 3-aminobenzo[d]isothiazole derivatives using the rat sciatic nerve model, Eur. J. Med. Chem., 44, 473- 481 (2009).

C. Papadopoulou, A. Geronikaki, D. Hadjipavlou-Litina, Synthesis and biological evaluation of new thiazolyl/ benzothiazolyl-amides, derivatives of 4-phenyl-piperazine, II Farmaco, 60, 969- 973 (2005).

A. Kreutzberger, H. Schimmelpfennig, Antiviral drugs, XVIII: 2-Aminothiazoles by cleavage of the S-S-bond of disulfidodicarbamidine, Arch. Pharm., 314, 385- 391 (1981).

E. Abdel-Latif, M. A. Metwally, F. A. Amer, M. E. Khalifa, Synthesis of 5-arylazo-2-(arylidenehydrazino)-thiazole disperse dyes for dyeing polyester fibres, Pigm. Resin. Technol., 38, 105–110 (2009).

M. A. Metwally, M. E. Khalifa, E. Abdel-Latif, F. A. Amer, New arylhydrazonothiazolidin-5-one disperse dyes for dyeing polyester fibers, Pol. J. Chem. Technol., 12, 1-6 (2010).

M. E. Khalifa, M. A. Metwally, E. Abdel-Latif, F. A. Amer, Synthesis of Some New 5-Arylazothiazole Derivatives as Disperse Dyes for Dyeing Polyester Fibers. Inter. J. Textile Science, 1, 62-68 (2012).

M. E. Khalifa, E. Abdel-Latif, A. A. Gobouri, Disperse Dyes Based on 5-Arylazo-thiazol-2-ylcarbamoyl-thiophenes: Synthesis, Antimicrobial Activity and Their Application on Polyester, J. Heterocycl. Chem., 52, 674-680, (2015).

A. Göblyös, S. N. Santiago, D. Pietra, T. Mulder-Krieger, J. F. D. Künzel, J. Brussee, A. P. Ijzerman, Synthesis and biological evaluation of 2-aminothiazoles and their amide derivatives on human adenosine receptors. Lack of effect of 2-aminothiazoles as allosteric enhancers, Bioorg. Med. Chem., 13, 2079-2087 (2005).

P. Beuchet, M. Varache-Lembège, A. Neveu, J. M. Léger, J. Vercauteren, S. Larrouture, G. Deffieux, A. Nuhrich, New 2-sulfonamidothiazoles substituted at C-4: synthesis of polyoxygenated aryl derivatives and in vitro evaluation of antifungal activity, Eur. J. Med. Chem., 34, 773-779 (1999).

A. Geronikaki, G. Theophilidis, Synthesis of 2-(aminoacetylamino)thiazole derivatives and comparison of their local anaesthetic activity by the method of action potential, Eur. J. Med. Chem., 27, 709-716 (1992).

P. Molyneux, The use of the stable free radical diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity, Songklanakarin J. Sci. Technol., 26, 211-219 (2004).

OECD Guideline for the testing of chemicals. Acute oral toxicity – acute toxic class method: Test no-423. Organization for Economic Co-operation and Development.

S. Daniel, M. D. Pratt, M. Marshall, M. D. Kaplan, Evaluation of Abnormal Liver-Enzyme Results in Asymptomatic Patients, Engl. J. Med., 342, 1266-1271 (2000).

E. Amador, L. E. Dorfman, W. E. C. Wacker, Serum Lactic Dehydrogenase Activity: An Analytical Assessment of Current Assays, Clin. Chem., 9, 391-399 (1963).

W. H. Habig, M. J. Pabst, W. B. Jakoby, Glutathione S-transferase AA from rat liver, Arch. of Biochem. and Biophy., 175, 710-716 (1976).

Y. Zeng, Y. Ren, Density functional theory study of tautomerization of 2-aminothiazole in the gas phase and in solution, Inter. J. Quantum Chem., 107, 247-258 (2007).

M. Nishikimi, N. A. Roa, K. Yogi, The occurrence of superoxide anion in the reaction of reduced phenazine methosulfate and molecular oxygen, Biochem. Bioph. Res. Common., 46, 849-854 (1972).

G. L. Ellman, A colorimetric method for determining low concentrations of mercaptans. Arch. Biochem. Biophys., 74, 443–450 (1958).

M. M. Bradford, A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding, Anal. Biochem., 72, 248–254 (1976).

L. Claisen, A. Claparède, Condensationen von Ketonen mit Aldehyden, Ber. Dtsch. Chem. Ges. 14, 2460–2468 (1881).

J. G. Schmidt, Ueber die Einwirkung von Aceton auf Furfurol und auf Bittermandelöl in Gegenwart von Alkalilauge, Ber. Dtsch. Chem. Ges., 14, 1459-1461(1881).

J. March, Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 3rd edn. Wiley, New York, USA, 1985.

T. Soderberg, Organic Chemistry with a Biological Emphasis, Chapter 11: Nucleophilic carbonyl addition reactions, Section 11.6: Imine (Schiff base) formation. http://chemwiki.ucdavis.edu/.

A. Schmidt, A. Dreger, Recent Advances in the Chemistry of Pyrazoles. Properties, Biological Activities, and Syntheses, Curr. Org. Chem., 15, 1423–1463 (2011).

M. Valko, C. J. Rhodes, J. Moncol, M. Izakovic, M. Mazur, Free radicals, metals and antioxidants in oxidative stress-induced cancer, Chemico..Biological Interactions, 160, 1-40 (2006).




DOI: http://dx.doi.org/10.20450/mjcce.2015.689

Refbacks

  • There are currently no refbacks.




Copyright (c) 2016 Mohamed Ezzat Khalifa, Mahmoud Abdel-Halim Mohamed, Noura Homoud Alshehri

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.