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Synthesis, Characterization and Biological Activity of New b-Lactam Analogues Bearing Pyrimidine and N-Acetamido Moieties
Corresponding Author(s) : Suror Abdulrahman Mahdi
Asian Journal of Chemistry,
Vol. 29 No. 5 (2017): Vol 29 Issue 5
Abstract
In this work, a series of new b-lactams were synthesized by Staudinger ketene-imine cyclo-addition reaction after multisteps synthesis. The first step involved preparation of N-acetamido amino acids (3-5) via reaction of acetic anhydride with amino acids (alanine, glycine, valine), since acetyl group is common protecting group for amine in organic synthesis. Treatment of compounds 3-5 with thionyl chloride in the second step gave N-acetamido amino acid chlorides (ketenes) (6-8) which in turn were treated with Schiff bases (imines) compounds 1 and 2, which derived from 2-amino pyrimidine and cinnamaldehyde or crotonaldehyde. In the third step to afford a series of the b-lactams (9-11) and (12-14). The synthesized compounds were identified by FT-IR and some of them by 1H NMR and 13C NMR. The synthesized b-lactams were screened for their antimicrobial activity against E. coli, Pseudomonas aeruginosa (Gram-negative), Staphylococcus aureus (Gram-positive) bacteria respectively and antifungal activity against Candida albicans.
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X.L. Zhao, Y.F. Zhao, S.C. Guo, H.S. Song, D. Wang and P. Gong, Molecules, 12, 1136 (2007); https://doi.org/10.3390/12051136.
R. Capdeville, E. Buchdunger, J. Zimmermann and A. Matter, Nat. Rev. Drug Discov., 1, 493 (2002); https://doi.org/10.1038/nrd839.
M. Stein-Gerlach, K. Salassidis, G. Bacher and S. Mueller, Pyridylpyrimidine Derivatives as Effective Compounds Against Prion Diseases, Int. Pat. Appl. WO 02/093164 A3 (2002).
L.K. Chao, K.F. Hua, H.Y. Hsu, S.S. Cheng, I.-F. Lin, C.-J. Chen, S.-T. Chen and S.-T. Chang, Food Chem. Toxicol., 46, 220 (2008); https://doi.org/10.1016/j.fct.2007.07.016.
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R.L. Danheiser and I. Okamoto, Org. Synth., 80, 160 (2003); https://doi.org/10.15227/orgsyn.080.0160.
U.M. Reddy, Org. Synth., 72, 14 (1995); https://doi.org/10.15227/orgsyn.072.0014.
A.A. Jarrahpour, M. Shekarriz and A. Taslimi, Molecules, 9, 939 (2004); https://doi.org/10.3390/91100939.
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A.W. Bauer, W.M. Kirby, J.C. Sherris and M. Turck, Am. J. Clin. Pathol., 45, 493 (1966).
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