Abstract
Herein we present the study of synthesis of novel bio-organometallic conjugates using 1,3-dipolar cycloaddition click reactions. Amino acid azides such as 4-azido-D-homoalanine, 5-azido-D-ornithine and 6-azido-D-lysine were reacted with ethynyl nickelocene to synthesize nickelocenyl-homoalanine conjugate (1), nickelocenyl-ornithine conjugate (2), and nickelocenyl–lysine conjugate (3) using Cu(I) compounds as catalysts. This synthetic strategy resulted in high yields (68–76%) of nickelocene-amino acid conjugates. Structure characterization of these purified bio-organometallic conjugates was performed using FT-IR, 1H, and 13C NMR spectroscopy. Antibacterial and antifungal activities of these products were tested against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Streptococcus pneumonia, Alternaria alternate, Aspergillus flavus, and Aspergillus niger using the disc diffusion method. Rifampicin (antibacterial) and fluconazole (antifungal) were used as standard drugs. Results of antimicrobial activities were found to be promising.
Similar content being viewed by others
Change history
21 May 2021
An Erratum to this paper has been published: https://doi.org/10.1134/S1070363221040290
References
Seiler, P., and Dunitz, J.D., Acta Cryst. B, 1980, vol. 36, p. 2255. doi org/10.1107/S0567740882007080
Elschenbroich, C., Organometallics, Weinheim: Wiley-VCH, 2006, ISBN 978-3-527-29390-2.
Sudhir, V.S., Kumar, N.P., and Chandrasekaran, S., Tetrahedron, 2010, vol. 66, p. 1327. doi org/10.1016/j.tet.2009.12.011
Metzler-Nolte, N., Angew. Chem. Int. Ed. 2001, vol. 40, p. 1040. doi 10.1002/1521-3773(20010316)40:6<1040:: AID-ANIE10400>3.0.CO;2-P
Scully, C.C. and Rutledge, P.J., Tetrahedron, 2010, vol. 66, p. 5653. doi org/10.1016/j.tet.2010.05.070
Van Staveren, D.R. and Metzler-Nolte, N., Chem. Rev., 2004, vol. 104, p. 5931. doi 10.1021/cr0101510
Huisgen, R., Szeimies, G., and Mobius, L., Eur. J. Inorg. Chem., 1967, vol. 100, p. 2494. doi 10.1002/cber.19671000806
Gothelf, K.V. and Jorgensen, K.A., Chem. Rev., 1998, vol. 98, p. 863. doi 10.1021/cr970324e
Kolb, H.C., Finn, M.G., and Sharpless, K.B., Angew. Chem. Int. Ed., 2001, vol. 40, p. 2004. doi 10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5
Lutz, J.F. and Borner, H.G., Prog. Polym. Sci., 2008, vol. 33, p. 1. doi org/10.1016/j.progpolymsci.2007.07.005
Tron, G.C., Pirali, T., Billington, R.A., Canonico, P.L., Sorba, G., and Genazzani, A.A., Med. Res. Rev., 2008, vol. 28, p. 278. doi 10.1002/med.20107
Braunschweig, A.B., Dichtel, W.R., Miljanic, O.S., Olson, M.A., Spruell, J.M., Khan, S.I., Heath, J.R., and Stoddart, J.F., Chem. Asian J., 2007, vol. 2, p. 634. doi 10.1002/asia.200700035
Devaraj, N.K. and Collman, J.P., QSAR Comb. Sci., 2007, vol. 26, p. 1253. doi 10.1002/qsar.200740121
Pasynkiewicz, S., Olȩdzka, E., and Pietrzykowski, A., Appl. Organomet. Chem., 2004, vol. 18, p. 583. doi 10.1002/aoc.743
Sutcliffe, O.B. and Bryce, M.R., Tetrahedron Asymmetry, 2003, vol. 14, p. 2297. doi org/10.1016/S0957-4166(03)00520-2
Nuzzi, A., Massi, A., and Dondoni, A., QSAR Comb. Sci., 2007, vol. 26, p. 1191. doi 10.1002/qsar.200740079
Dondoni, A. and Marra, A., J. Org. Chem., 2006, vol. 71, p. 7546. doi 10.1021/jo0607156
Fernandez-Megia, E., Correa, J., Rodríguez-Meizoso, I., and Riguera, R., Macromol., 2006, vol. 39, p. 2113. doi 10.1021/ma052448w
Gierlich, J., Burley, G.A., Gramlich, P.M.E., Hammond, D.M., and Carell, T., Org. Lett., 2006, vol. 8, p. 3639. doi 10.1021/ol0610946
Rozkiewicz, D.I., Janczewski, D., Verboom, W., Ravoo, B.J., and Reinhoudt, D.N., Angew. Chem. Int. Ed., 2006, vol. 45, p. 5292. doi 10.1002/anie.200601090
Guo, Z., Lei, A., Liang, X., and Xu, Q., Chem. Commun., 2006, p. 4512. doi 10.1039/B610733H
Müller, G. and Kramer, A., J. Antimicrob. Chemother., 2008, vol. 61, p. 1281. doi org/10.1093/jac/dkn125
Raza, M. A., Pervaiz, M., Rashid, A., Mustafa, H., and Adnan, A., Asian J. Chem., 2016, vol. 28, p. 954. doi org/10.14233/ajchem.2016.19277
Bondi, Jr. A., Spaulding, E.H., Smith, D.E., and Dietz, C.C., Am. J. Med. Sci., 1947, vol. 213, p. 221.
Author information
Authors and Affiliations
Corresponding author
Additional information
The text was submitted by the authors in English.
Rights and permissions
About this article
Cite this article
Raza, M.A., Amin, M., Muhammad, G. et al. Synthesis of biologically active nickelocenyl–amino acid conjugates using 1,3-dipolar cycloaddition click reactions. Russ J Gen Chem 87, 2678–2683 (2017). https://doi.org/10.1134/S107036321711024X
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S107036321711024X