SYNTHESIS, CHARACTERIZATION, AND BIOLOGICAL EVALUATION OF OXAZOLONE ANALOGS

Muthuboopathi G

doi:10.22159/ajpcr.2018.v11s4.31726

Authors

Muthuboopathi G Department of Pharmaceutics, School of Pharmaceutical Sciences, VISTAS, Chennai - 600 117, Tamil Nadu, India.

DOI:

https://doi.org/10.22159/ajpcr.2018.v11s4.31726

Keywords:

Glycine, Acetic anhydride, Acetyl glycine, Oxazolone analogs, Fourier-transform infrared spectroscopy, Anti-inflammatory, Human red blood cell membrane stabilization method

Abstract

Objective: The main objective of the study is to synthesize some novel oxazolone derivatives to evaluate for anti-inflammatory activity.

Methods: Acetylglycine was prepared using glycine and acetic anhydride, and the prepared acetylglycine was condensed with different aromatic aldehydes to get novel oxazolone derivatives. The synthesized compound was carried out the characterization by Fourier-transform infrared spectroscopy and find the anti-inflammatory by human red blood cell (HRBC) membrane stabilization method.

Results: The anti-inflammatory activity was performed using novel oxazolone derivatives (Cpd1, Cpd2, Cpd3, and Cpd4) and nimesulide (as standard) on HRBC membrane stabilization method. The percentage protection was observed using colorimeter. The synthesized oxazolone was compared with the standard drug nimesulide for anti-inflammatory using HRBC membrane stabilizing method. All the synthesized oxazolone derivatives have shown the anti-inflammatory activity as that of standard. The results can be easily interpreted using histograms.

Conclusions: Among all the synthesized compounds, oxazolone with 4-chlorobenzaldehyde shows more anti-inflammatory activity when compared with the other oxazolone derivatives.

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References

Ahluwalia KV. Erlenmeyer-plochl azalactone and amino acid synthesis. In: Comprehensive Practical Organic Chemistry. Preparations and Quantitative Analysis. ???: Universities Press; 2000.

Anosike CA, Obidoa O, Ezeanyika LU. Membrane stabilization as a mechanism of the anti-inflammatory activity of methanol extract of garden egg (Solanum aethiopicum). Daru 2012;20:76.

Stinchcomb AL. In vivo evaluation of a transdermal codrug of 6-Î²-naltrexol linked to hydroxybupropion in hairless guinea pigs. Eur J Pharm Sci 2008;33:371-9.

Boniface PK, Verma S, Shukla A. Membrane stabilisation: A possible antiinflammatory mechanism for the extracts and compounds from Spathodea campanulata. Nat Prod Res 2014;28:2203-7.

Cushman DW, Cheung HS, Sbo EF, Ondetti MA. Design of potent competitive inhibitors of angiotensin converting enzyme. carboxyalkanoyl and mercaptoalkanoyl amino acids. Biochemistry 1977;16:5484-91.

Graves BJ, Hatada MH, Miller JK, Graves MC, Roy S, Cook CM, et al. The three dimensional x-ray crystal structure of HIV-1 protease complexed with a hydroxyethylene inhibitor. Adv Exp Med Biol 1991;306:455-60.

Griffin C, Karnik A, McNulty J, Pandey S. Pancratistatin selectively targets cancer cell mitochondria and reduces growth of human colon tumor xenografts. Mol Cancer Ther 2011;10:57.

Kim KH, Greco G, Novellino E. In: Kubinyi H, Folkers G, Martin YC, editors. 3D QSAR in Drug Design. Dordrecht: Kluwer Academic Publishers; 1998. p. 257.

Kuntz ID, Blaney JM, Oatley SJ, Langridge R, Ferrin TE. A geometric approach to macromolecule-ligand interactions. J Mol Biol 1982;161:269-88.

Osman MO, Hassan HM, Moawad EB, El-Mekabaty A. Reactivity of oxazolone derivative towards nitrogen and carbon nucleophilic reagents: Applications to the synthesis of new heterocycles. Int J Modern Org Chem 2013;2;11-25.

Sanchez C, Mendez C, Salas JA. Indolocarbazole natural products: Occurrence, biosynthesis and biological activity. Nat Prod Rep 2006;23:1007-45.

Seelmeier S, Schmidt H, Turk V, von der Helm K. Human immunodeficiency virus has an aspartic-type protease that can be inhibited by pepstatin A. Proc Natl Acad Sci USA 1988;85:6612-6.

Laeeq S, Sirbaiya AK, Siddiqui HH, Mehdi S, Zaidi H. An overview of the computer aided drug designing. World J Pharm Pharm Sci 2014;3:5.

Tandel RC, Mammen D. Synthesis and study of some compounds containing oxazolone ring showing biological activity. Indian J Chem 2008; 47:932-7.

Tikdari MA, Fozooni S, Hamidian H. Dodecatungstophosphoric acid (H3PW12O40), samarium and ruthenium (Ð†Ð†Ð†) chloride catalyzed synthesis of unsaturated 2-phenyl-5(4H)-oxazolone derivatives under solvent-free conditions. Molecules 2008;13:3246-52.

Uwe R. The dynamic structure of jadomycin b and the amino acid incorporation step of its biosynthesis. J Am Chem Soc 2004; 126:

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