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Abstract
The Sugar derived aziridine was obtained from iodo-aziridines through in situ nucleophilic expulsion of iodine using glucosamine as a nucleophile. This work describes new results of our ongoing research targeting new aziridines of biological interest. All the compounds were screened for their antibacterial activity, they all showed comparable moderate to good growth inhibitory activity with reference to Tetracyclin, Ciprofloxacine and Gentamicin.
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Keniche A., Mezrai A., Kajima Mulengi J.,Novel class of phosphonoaziridines as antibacterial agents, The Open Conference Proceedings Journal, Dubai, 2 (2011) 28-36.
Dandekar, T., Dandekar, G., Pharmacogenomic strategies against microbial resistance: from bright to bleak to innovative, Pharmacogenomics,11 (2010) 1193 -1196.
Neu, H. C., The crisis in antibiotic resistance, Science , 257 (1992)1064 -1073.
Monroe, S., Polk, R., Antimicrobial use and bacterial resistance, Curr. Opin. Microbiol, 3 (2000) 496–501.
Kunin, C. M., Why did it take the Infectious Diseases Society of America so long to address the problem of antibiotic resistance?, Clin. Infect. Dis. 46 (2008) 1792–1794.
Antimicrobial resistance: global report on surveillance (2014), WHO. http://www.who.int/drugresistance/documents/surveillancereport/en/.
Fabbretti, A., Gualerzi, C. O., Brandi, How to cope with the quest antibiotics, L. FEBS Lett, 585 (2011) 1673–1681.
Grunenberg, J., Licari, G., Effective in silico prediction of new oxazolidinone antibiotics: force field simulations of the antibiotic–ribosome complex supervised by experiment and electronic structure methods, Beilstein J. Org. Chem, 12 (2016 )415–428.
Giovine A., Muraglia M., Antonio Florio M., Rosato A., Corbo F., Franchini C., Musio B., Degennaro L. Luisi, R., Synthesis of Functionalized Arylaziridines as Potential Antimicrobial Agents Molecules, 19 (2014) 11505-11519.
Steven Vega-Pérez J.M., Palo-Nieto C., Vega-Holm M., Góngora-Vargas P., Calderón-Montaño J.M., Burgos-Morón E., López-Lázaro M., Iglesias-Guerra F., Aziridines from alkenyl-β-D-galactopyranoside derivatives: Stereoselective synthesis and in vitro selective anticancer activity, European Journal of Medicinal Chemistry, 70 (2013) 380-392.
D’hooghe M., Kenis S., Vervisch K., Lategan C., Smith P.J., Chibale K., De Kimpe N., Synthesis of 2-(aminomethyl)aziridines and their microwave-assisted ring opening to 1,2,3-triaminopropanes as novel antimalarial pharmacophores, European Journal of Medicinal Chemistry, 46 (2011) 579-587.
Grif, K.; Dierich, M. P.; Pfaller, K.; Miglioli, P. A.; Allenberger, F. In vitro activity of fosfomycin in combination with various antistaphylococcal substances. J. Antimicrob. Chemother, 48 (2001) 209-217.
Fahey, K.; Aldabbagh, F. The influence of the aziridinyl substituent of benzimidazoles and benzimidazolequinones on toxicity towards normal and Fanconi anaemia cells. Tetrahedron Lett., 49, (2008) 5235–5237.
Fahey, K.; O’Donovan, L.; Carr, M.; Carty, M.P.; Aldabbagh, F. Synthesis and toxicity towards normal and cancer cell lines of benzimidazolequinones containing fused aromatic rings and 2-aromatic ring substituents. Eur. J. Med. Chem., 45 (2010) 1873–1879.
Prosser, G.A.; Copp. J. N.; Syddall, S.P.; Williams, E. M.; Smaill,J. B.; Wolson, W.R.; Patterson, A.V.; Ackerley, D.F. Discoveryand evaluation of Escherichia coli nitroreductases that activate theanti-cancer prodrug CB1954. Biochem. Pharmacol., (2010) 678-687.
Sucre, A.P.; Vicik, R.; Schultheis, M.; Schirmeister,T.; Moll, H. Aziridine-2,3-dicarboxylates, peptidomimetic cysteine protease inhibitors with antileishmanial activity, antimicrobial. Agents Chemother., 50 (2006) 2439-2447.
Hanessian, S.; Moitessier, N.; Cantin, L.D. Design and synthesis of MMP inhibitors using N-arylsulfonylaziridine hydroxamic acids as constrained scaffolds. Tetrahedron., 57 (2001) 6885-6900.
Schirmeier, T.; Peric, M. Aziridinyl peptides as inhibitors of cysteine proteases: effect of a free carboxylic acid function on inhibition. Bioorg. Med. Chem., 8 (2008) 1281-1291.
Ismail, M.D.; Levitsky, D.O.; Dembitsky, V.M. Aziridine alkaloids as potential therapeutic agents. Eur. J. Med. Chem., 44 (2009) 3373-3387.
Sharma, P.; Kumar, A.; Upadhyay, S.; Sahu, V.; Singh, J. Synthesis and QSAR modeling of 2-acetyl-2-ethoxycarbonyl-1-[4(4'-arylazo)-phenyl]-N,N-dimethylaminophenyl aziridines as potential antibacterial agents. Eur. J. Med. Chem., 44 (2009) 251-259.
Medjahed, W.; Tabet Zatla, A.; Kajima Mulengi,J.; Baba Ahmed,F.Z.; Merzouk, H. The synthesis of N-acyl-2-hydroxymethyl aziridines of biological interest. Tetrahedron Lett., 45 (2004) 1211-1213.
Baba Ahmed, F. Z.; Bouanane, S.; Merzouk, S. A.; Merzouk, H.; Medjahed, W.; Kajima Mulengi,J.; Prost, J. 2-hydroxymethyl-1-(Nphtaloyltriptophyl) aziridine stimulates in vitro human lymphocyte proliferation and interleukin secretion. Pathol. Biol., 56 (2008) 137–142.
Baba Ahmed, F.Z.; Merzouk, H.; Bouanane, S.; Benkalfat, N. B.;Merzouk, S.A.; Kajima Mulengi, J.; Narce, M. Evaluation de la toxicité aiguë de la 2-hydroxyméthyl-1(Nphtaloyltryptophyl) aziridine chez le rat Wistar. Ann Toxicol Anal. (2010) DOI: 10.1051/ata/2010017. www.ata-journal.org
J.Kajima Mulengi, A. Keniche, A. Mezrai, F.Djedaini Pillard, V.Bonnet, Asian Journal of Materials Chemistry, 1 (2016) 38-45.
Keniche A., Drici W., Slimani M.Z., Mezrai A., Kajima Mulengi J., 1,3-Dipolar cycloaddition of azomethine ylide from Phtaloylimidophenylalanyl-2-hydroxymethylaziridine Mediterr.J.Chem, 2 (2013) 583-594.
J.Kajima Mulengi, A. Keniche Slimani, A Bit of Chemistry of aziridines and application, Ed : LAP, 2016, p.80.
Keniche, A., Bellifa, S., Hssaine, H., Slimani M.Z., Kajima Mulengi J., Algerian J. Nat. Products, 4 (2016) 226-232.
Keniche A., Mezrai A., Kajima Mulengi J.,Novel class of phosphonoaziridines as antibacterial agents, The Open Conference Proceedings Journal, Dubai, 2 (2011) 28-36.
Andrez, J.C, Mitomycins syntheses: a recent update, Beilstein Journal of Organic Chemistry , 5 (2009) 1-36.
Dembitsky, V. M., Terent'ev, A. O., Levitsky, D. O. Aziridine Alkaloids: Origin, Chemistry and Activity. In Natural Products; Eds.; Springer-Verlag: Berlin, Heidelberg, (2013) 977–1006.
Lowden, P. A. S., Aziridine Natural Products Discovery, Biological Acitvity and Biosynthesis. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley VCH: Weinheim, Germany, 2006; pp 399–442. doi:10.1002/3527607862.ch11
Sun, H., Huang, B., Lin,R., Yang, C., Xia, W., Metal-free one-pot synthesis of 2-substituted and 2,3-disubstituted morpholines from aziridines, Beilstein J. Org. Chem. 11 (2015) 524–529.
Dnyaneshwar, N., Subhash, G., Tanpure, D., Mhaske, B., Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8–DMSO: application to the synthesis of vernakalant, Beilstein J. Org. Chem. 11 (2015) 1008–1016.
Wan,J.P., Jing, Y., Beilstein, Recent advances in copper-catalyzed C–H bond amidation, J. Org. Chem., 11 (2015) 2209–2222.
Francke, R., Recent advances in the electrochemical construction of heterocycles, Beilstein J. Org. Chem. &à (2014) 2858–2873.
Armstrong, A., Ferguson,A., Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines, Beilstein J. Org. Chem. , 8 (2012) 1747–1752.
Ashley N. Jarvis1, Andrew B. McLaren1, Helen M. I. Osborn and Joseph Sweeney, Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines Beilstein J. Org. Chem. , 852–859.
Ping-An Wang, Organocatalyzed enantioselective desymmetrization of aziridines and epoxides, Beilstein J. Org. Chem., 9 (2013) 1677–1695.
Tao, J., Jin, L.M., Peter Zhang,X., Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis, Beilstein J. Org. Chem., 10 (2014) 1282–1289.
Xia, X., H. Toy,P., Rasta resin–triphenylphosphine oxides and their use as recyclable heterogeneous reagent precursors in halogenation reactions Beilstein J. Org. Chem., 10 (2014) 1397–1405.
Xiong, Y., Qian,P., Cao,C., Mei, H., Han, J., Li, G., Pan, Y., One-pot stereoselective synthesis of α,β-differentiated diamino esters via the sequence of aminochlorination, aziridination and intermolecular SN2 reaction Beilstein J. Org. Chem. 10 (2014) 1802–1807.
Florio, S., Troisi, L., Capriati, V., Ingrosso, G., Synthesis of oxazolinyl aziridines, Tetrahedron Letters, 40 (1999) 6101-6104.
Kroger, L., Henkensmeier, D., Schafer, A., Thiem, J., Novel O-glycosyl amino acid mimetics as building blocks for O-glycopeptides act as inhibitors of galactosidases, Bio.Med. Chem.Lett, 14 (2004) 73-75.
DOI: http://dx.doi.org/10.5281/zenodo.1473136
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