Synthesis and Antimicrobial activities of Aziridines-tosylates Derivative

Assia Keniche

Abstract


By using simple straightforward synthesis of Tosylate aziridines has been developed. By means of this synthetic strategy from readily available N-phtaloyl acide and 2-methylbenzosulfonate aziridine using DCC as coupling agent, new tosylates aziridines could be obtained. The coupling reactions occurred without ring opening of the three membered ring. This work describes new results of our ongoing research targeting new derivatives 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 and Gentamicin.


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Cesar, A. Arias, M.D., Barbara E., Murray, M.D.; A New Antibiotic and the Evolution of Resistance. N Engl J Med (2015) 372 :1168-1170.

Z.Lu, X.Zhang, Z.Li, Z.Wu, J.Song, C.Li, Antibacterial activity of cationic polymers: side-chain or main-chain type? Polym Chem, 6 (2015) 772-779.

Khalaj, A., Nakhjiri, M., Negahbani, A.S., Samadizadeh, M., Firoozpour, L., Rajabalian, S., Samadi, N., Faramarzi, M.A., Dibpour, N.A., Shafiee, A., Foroumadi, A., Discovery of a novel nitroimidazolyl-oxazolidinone hybrid with potent anti Gram-positive activity: Synthesis and antibacterial evaluation Eur.J.Med.Chem, 46 (2011) 65-70.

Pinkner, J.S., Remaut, H., Buelens, F., Miller, E., Åberg, V., Pemberton, N., Hedenström, M., Larsson, A., Seed, P., Waksman, G., Hultgren, S.J., Almqvist, F., Rationally designed small compounds inhibit pilus biogenesis in uropathogenic bacteria. Proc. Natl. Acad. Sci. U.S.A., 103 (2006) 17897-17902.

Meka, G., K.Pillai, S., Sakoulas, G., Wennersten, C.V., Venkataraman, L., DeGirolami, P.C., Eliopoulos, G.M., Moellering, R.C., Gold, H.S., Linezolid Resistance in Sequential Staphylococcus aureus Isolates Associated with a T2500A Mutation in the 23S rRNA Gene and Loss of a Single Copy of Rrna. J. Infect. Dis. DrugTargets, 190 (2004) 311-317.

Levy, S.B., Marshall, B. Antibacterial resistance worldwide: causes, challenges and responses. Nat Med. (2004) 10, 122–129.

Keniche, A, Bellifa, S., Hassaine, H., Kajima Mulengi, J., Synthesis and Evaluation of Biological Activity of Novel Sugar-Derived Aziridines, Algerian J. Nat. Products, (2018) 6, 609-617.

Keniche A., Mezrai A., Kajima Mulengi J., Novel class of phosphonoaziridines as antibacterial agents, The Open Conference Proceedings Journal, Dubai, 2 (2011) 28-36.

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 2014, 19, 11505-11519.

Moonen K., Laureyn I., Stevens C.V., Synthetic methods for azaheterocyclic phosphonates and their biological activity, Chem. Rev., 104 (2004) 6177-6215.

Fahey, K., Aldabbagh, F. The influence of the aziridinyl substituent of benzimidazoles and benzimidazolequinones on toxicity towards normal and Fanconi anaemia cells. Tetrahedron Lett., (2008) 49, 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., (2010) 45, 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. Discovery and evaluation of Escherichia coli nitroreductases that activate the anti-cancer prodrug CB1954. Biochem. Pharmacol., (2010) 79, 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., (2006) 50, 2439-2447.

Hanessian, S., Moitessier, N., Cantin, L.D. Design and synthesis of MMP inhibitors using N-arylsulfonylaziridine hydroxamic acids as constrained scaffolds. Tetrahedron., (2001) 57, 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., (2000) 8, 1281-1291.

Ismail, M.D., Levitsky, D.O., Dembitsky, V.M. Aziridine alkaloids as potential therapeutic agents. Eur. J. Med. Chem. (2009) 44, 3373-3387.

J. B. Sweeney, Aziridines: epoxides ugly cousins?, Chem. Soc. Rev., 31 (2002) 247.

Watson, I. D. , Yu, L., Yudin, A. K. Sriramurthy, Silylmethyl-Substituted Aziridine and Azetidine as Masked 1,3- and 1,4-Dipoles for Formal [3 + 2] and [4 + 2] Cycloaddition Reactions.J. Am. Chem. Soc., 127 (2005) 16366-67.

Da Silva,A.R., dos Santos,A.D., Paixão, M.W., Gonçalves Corrêa, A., Stereoselective Multicomponent Reactions in the Synthesis or Transformations of Epoxides and Aziridines, Molecules. (2019) 24, 630.

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.

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.

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.

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.

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.

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.

W.Medjahed, A.Tabet Zatla, J.Kajima Mulengi, F.Z.BabaAhmed, H.Merzouk, Tetrahedron Lett., 45 (2004) 1211.

Keniche A., Slimani MZ., José Miranda I., Azipura Jesus M., Kajima Mulengi J., NMR Investigation of the complexation of (S)-2-isopropyl-1-(o-nitrophenyl)sulfonyl)aziridine withb-cyclodextrine , Mediterr.J.Chem, 2 (2014) 620-631.

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.

Baba Ahmed, F.Z., Bouanane, S., Merzouk, S.A., Merzouk, H., Medjahed, W., Kajima Mulengi, J., Prost, J., Pathol.Biol., 46 (2008) 137.

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

Keniche,A., Bellifa,S., Hassaine,H., Slimani,M.Z., Kajima Mulengi, J. EVALUATION OF ANTIBACTERIAL ACTIVITIES OF NOVEL AZIRIDINYL PHOSPHONATES, Algerian J. Nat. Products, (2016) 4, 226-232.

Brock Dyer,F., Park,C.M., Joseph,R., Garner, P., Aziridine-Mediated Ligation and Site-Specific Modification of Unprotected Peptides, J. Am. Chem. Soc. (2011) 133 20033–20035.

Bromberg,L., Bromberg, D.J., Alan Hatton, T., Bandín,I., Concheiro,A., Alvarez-Lorenzo, C., Antiviral Properties of Polymeric Aziridine- and Biguanide-Modified Core–Shell Magnetic Nanoparticles,. Langmuir. (2012) 28 4548–4558.

Mladenovic, M., Engels, B., Schirmeister, T., Rational Design of Improved Aziridine-Based Inhibitors of Cysteine Proteases. J. Phys. Chem. B, (2009) 113 5282–5289.

Galonić, P.D., van der Donk, W.A., Gin, Y.A. Site-Selective Conjugation of Thiols with Aziridine-2-Carboxylic Acid-Containing Peptides. J. Am. Chem. Soc. (2004) 126 12712–12713

Kim,H.J., Chaikittisilp, W., Jang,K.S., Didas, S.A., Johnson,J.R., Koros,W.J., Nair,S., Christopher, W. Aziridine-Functionalized Mesoporous Silica Membranes on Polymeric Hollow Fibers: Synthesis and Single-Component CO2 and N2 Permeation Properties? Jones Ind. Eng. Chem. Res. (2015) 54, 4407–4413.

Murray, C., Dyer, F.B., Garner, P. Solid phase synthesis and ligative processing of photocaged aziridine-2-carbonyl-terminated peptides, Tetrahedron Letters, 56, (2015) 3636-3638,

Synthesis of densely functionalized cispentacin derivatives through selective aziridination and aziridine opening reactions: orthogonally protected di- and triaminocyclopentanecarboxylates, Tetrahedron, 70 (2014) 8511-8519.

Nonn,M., Kiss,L., Forró,E., Sillanpää,R., Fülöp,F., A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis Tetrahedron Letters. 56, (2015) 1276-1279.

Timothy J. Senter, Matthew C. O’Reilly, Katherine M. Chong, Gary A. Sulikowski, Craig W. Lindsley, Koide, S; Sidhu, S. The importance of being tyrosine: lessons in molecular recognition from minimalist synthetic binding proteins.ACS Chem. Biol., (2009) 4, 325-334.

Applegate, H. E.; Cimarusti, C. M.; Dolfini, J. E.; Funke, P. T.;Koster, W. H.; Puar, M. S.; Slusarchyk, W. A.; Young, M. G.Synthesis of 2-, 4-, and 7-methylthio-substituted cephalosporins. J.Org. Chem. (1979) 44, 811-818.

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.

Vederas, V.C., Bader, A. Diaminopimelate and lysine biosynthesis—Anantimicrobial target in bacteria. Can. J. Chem. (2006) 84, 1197–1207.

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.

Ismail, M.D., Levitsky, D.O., Dembitsky, V.M. Aziridine alkaloids as potential therapeutic agents. Eur. J.Med. Chem., 44 (2009) 3373-3387.

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.




DOI: http://dx.doi.org/10.5281/zenodo.4282237

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