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Copyright (c) 2014 Fatin Nur Ain Abdul Rashid1, Asnuzilawati Asari1, Habsah Mohamad2, Siti Mariam Mohd Nor3
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Antibacterial Study of Aaptamine Derivatives
Corresponding Author(s) : Fatin Nur Ain Abdul Rashid1
Asian Journal of Chemistry,
Vol. 26 No. 20 (2014)
Abstract
Aaptamine is a bioactive marine alkaloid containing a unique of 1H-benzo[de][1,6]naphthyridine skeleton. Aaptamine was isolated from marine sponge, Aaptos aaptos and was proposed as starting material for semi-synthetic modifications. A series of aaptamine derivatives were synthesized which consisted of 1,4-dialkyl (2-7), 4-alkyl (8-10) and 9-O-butyryl-1,4-dialkyl (11-16) aaptamine derivatives. Each derivative was characterized by FT-IR, UV-visible, NMR and MS. The synthesized compounds were evaluated for their antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Bacillus cereus, Staphylococcus aureus and Micrococcus sp. bacterial strains using the disc-diffusion method. Some of the derivatives showed potent antibacterial activity against certain bacterial strains.
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References
B. Fugmann, B. Steffan and W. Steglich, Tetrahedron Lett., 25, 3575 (1984).
H. Nakamura, J. Kobayashi, Y. Ohizumi and Y. Hirata, Tetrahedron Lett., 23, 5555 (1982).
L. Calcul, A. Longeon, A.A. Mourabit, M. Guyot and M.L. Bourguet-Kondracki, Tetrahedron, 59, 6539 (2003).
R. de A. Epifanio, A.F. Coutinho, B. Chanas, T.M.L. e Souza and I.C.P.P. Frugrulhetti, Heterocycles, 57, 1265 (2002).
A. Herlt, L. Mander, W. Rombang, R. Rumampuk, S. Soemitro, W. Steglich, P. Tarigan and F. von Nussbaum, Tetrahedron, 60, 6101 (2004).
A. Rudi and Y. Kashman, Tetrahedron Lett., 34, 4683 (1993).
K. Shaari, K.C. Ling, Z. Mat Rashid, T.P. Jean, F. Abas, S.M. Raof, Z. Zainal, N.H. Lajis, H. Mohamad and A.M. Ali, Mar. Drugs, 7, 1 (2009).
G.R. Pettit, H. Hoffmann, D.L. Herald, P.M. Blumberg, E. Hamel, J.M. Schmidt, Y. Chang, R.K. Pettit, N.E. Lewin and L.V. Pearce, J. Med. Chem., 47, 1775 (2004).
G.R. Pettit, H. Hoffmann, D.L. Herald, J. Mcnulty, A. Murphy, K.C. Higgs, E. Hamel, N.E. Lewin, L.V. Pearce, P.M. Blumberg, R.K. Pettit and J.C. Knight, J. Org. Chem., 69, 2251 (2004).
Y. Takahashi, N. Tanaka, T. Kubota, H. Ishiyama, A. Shibazaki, T. Gonoi, J. Fromont and J. Kobayashi, Tetrahedron, 68, 8545 (2012).
Y.C. Shen, T.T. Lin, J.H. Sheu and C.Y. Duh, J. Nat. Prod., 62, 1264 (1999).
J.J. Bowling, H.K. Pennaka, K. Ivey, S. Wahyuono, M. Kelly, R.F. Schinazi, F.A. Valeriote, D.E. Graves and M.T. Hamann, Chem. Biol. Drug Des., 71, 205 (2008).
W. Gul, N.L. Hammond, M. Yousaf, J.J. Bowling, R.F. Schinazi, S.S. Wirtz, G.C. Andrews, C. Cuevas and M.T. Hamann, Bioorg. Med. Chem., 14, 8495 (2006).
M.M. Mackeen, A.M. Ali, N.H. Lajis, K. Kawazu, Z. Hassan, M. Amran, M. Habsah, L.Y. Mooi and S.M. Mohamed, J. Ethnopharmacol., 72, 395 (2000).
E.L. Larghi, M.L. Bohn and T.S. Kaufman, Tetrahedron, 65, 4257 (2009).