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Synthesis, Antibacterial Activity and Antifouling Property of Novel Indole Compounds Containing Acylamino Groups
Corresponding Author(s) : Xue-Feng Yan
Asian Journal of Chemistry,
Vol. 26 No. 18 (2014): Vol 26 Issue 18
Abstract
Due to the environmentally harmful impact of tributyltin self-polishing paints and other "tributyltin-free" chemically active paints, there is a critical need of more ecological alternatives. In this work, 9 novel N-substituted indoles each bearing a acylamino group were synthesized and the structures of 2a-2i were established by 1H NMR, IR spectra and elemental analysis. The antibacterial activity of the synthesized compounds against Escherichia coli and Staphylococcus aureus as well as antifouling activity were studied. The results showed that these compounds possessed a broad spectrum of activity having MIC values of 0.01-0.5 mg/mL against the tested bacteria and antifouling property was superior to cuprous oxide which is widely used as antifoulants. This provided theoretical and technical support for the preparation of environmental friendly antifouling coatings.
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- M.A. Champ, Mar. Pollut. Bull., 46, 935 (2003); doi:10.1016/S0025-326X(03)00106-1.
- D.E. Moreland, Annu. Rev. Plant Physiol., 31, 597 (1980); doi:10.1146/annurev.pp.31.060180.003121.
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- N.M. Targett, S.S. Bishop, O.J. McConnell and J.A. Yoder, J. Chem. Ecol., 9, 817 (1983); doi:10.1007/BF00987807.
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- H. Morii, Y. Izumi, K. Kasama and R. Ishimoto, Fish. Sci., 60, 773 (1994); doi:10.2331/suisan.60.773.
- G. Olguin-uribe, E. Abou-mansour, A. Boulander, H. Débard, C. Francisco and G. Combaut, J. Chem. Ecol., 23, 2507 (1997); doi:10.1023/B:JOEC.0000006663.28348.03.
- N. Yamaguchi, K. Matsuzawa, M. Kono et al., JP Patent 2002053410 (2002).
- Y. Shizuri, J. Tanaka, J. Fukunaga et al., JP Patent 2003055112 (2003).
- X. Li, L.M. Yu, X.H. Jiang, S. Xia and H. Zhao, Chin. J. Oceanology Limnol., 27, 309 (2009); doi:10.1007/s00343-009-9212-1.
- W.W. Cong, L.M. Yu, X.H. Jiang, X. Li and H.Z. Zhao, Materials Rev., 25, 37 (2011).
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- W.W. Cong and L.M. Yu, Chem. Res. Chin. Univ., 27, 803 (2011).
- Antifouling Panels in Shallow Submergence, Patent GB/T 5370-85.
- P. Hamel and M. Girard, J. Org. Chem., 65, 3123 (2000); doi:10.1021/jo9919207.
References
M.A. Champ, Mar. Pollut. Bull., 46, 935 (2003); doi:10.1016/S0025-326X(03)00106-1.
D.E. Moreland, Annu. Rev. Plant Physiol., 31, 597 (1980); doi:10.1146/annurev.pp.31.060180.003121.
A. Koutsaftis and I. Aoyama, Sci. Total Environ., 387, 166 (2007); doi:10.1016/j.scitotenv.2007.07.023.
F. Cima, M. Bragadin and L. Ballarin, Aquat. Toxicol., 86, 299 (2008); doi:10.1016/j.aquatox.2007.11.010.
N.M. Targett, S.S. Bishop, O.J. McConnell and J.A. Yoder, J. Chem. Ecol., 9, 817 (1983); doi:10.1007/BF00987807.
M. Sjögren, U. Göransson, A.L. Johnson, M. Dahlström, R. Andersson, J. Bergman, P.R. Jonsson and L. Bohlin, J. Nat. Prod., 67, 368 (2004); doi:10.1021/np0302403.
N.A. Paul, R. de Nys and P.D. Steinberg, Mar. Ecol. Prog. Ser., 306, 87 (2006); doi:10.3354/meps306087.
A. Bazes, A. Silkina, D. Defer, C. Bernède-Bauduin, E. Quéméner, J.-P. Braud and N. Bourgougnon, Aquaculture, 258, 664 (2006); doi:10.1016/j.aquaculture.2006.04.017.
H. Morii, Y. Izumi, K. Kasama and R. Ishimoto, Fish. Sci., 60, 773 (1994); doi:10.2331/suisan.60.773.
G. Olguin-uribe, E. Abou-mansour, A. Boulander, H. Débard, C. Francisco and G. Combaut, J. Chem. Ecol., 23, 2507 (1997); doi:10.1023/B:JOEC.0000006663.28348.03.
N. Yamaguchi, K. Matsuzawa, M. Kono et al., JP Patent 2002053410 (2002).
Y. Shizuri, J. Tanaka, J. Fukunaga et al., JP Patent 2003055112 (2003).
X. Li, L.M. Yu, X.H. Jiang, S. Xia and H. Zhao, Chin. J. Oceanology Limnol., 27, 309 (2009); doi:10.1007/s00343-009-9212-1.
W.W. Cong, L.M. Yu, X.H. Jiang, X. Li and H.Z. Zhao, Materials Rev., 25, 37 (2011).
F.S. Chen and Y.P. Xu, CN Patent 101045909 (2007).
W.W. Cong and L.M. Yu, Chem. Res. Chin. Univ., 27, 803 (2011).
Antifouling Panels in Shallow Submergence, Patent GB/T 5370-85.
P. Hamel and M. Girard, J. Org. Chem., 65, 3123 (2000); doi:10.1021/jo9919207.