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Original Article

Synthesis and antimicrobial studies of novel 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one 4′-phenylthiosemicarbazones

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Pages 430-439 | Received 09 Apr 2010, Accepted 17 Sep 2010, Published online: 28 Oct 2010

References

  • Zanatta, N., Alves, S.H., Coelho, H.S., Borchhardt, D.M., Machado, P., Flores, K.M., da Silva, F.M., Spader, T.B., Santurio, J.M., Bonacorso, H.G., Martins, M.A. Synthesis, antimicrobial activity, and QSAR studies of furan-3-carboxamides. Bioorg. Med. Chem. 2007, 15, 1947–1958.
  • Khalafi-Nezhad, A., Soltani Rad, M.N., Mohabatkar, H., Asrari, Z., Hemmateenejad, B. Design, synthesis, antibacterial and QSAR studies of benzimidazole and imidazole chloroaryloxyalkyl derivatives. Bioorg. Med. Chem. 2005, 13, 1931–1938.
  • Ghosh, S., Misra, A.K., Bhatia, G., Khan, M.M., Khanna, A.K. Syntheses and evaluation of glucosyl aryl thiosemicarbazide and glucosyl thiosemicarbazone derivatives as antioxidant and anti-dyslipidemic agents. Bioorg. Med. Chem. Lett. 2009, 19, 386–389.
  • Siles, R., Chen, S.E., Zhou, M., Pinney, K.G., Trawick, M.L. Design, synthesis, and biochemical evaluation of novel cruzain inhibitors with potential application in the treatment of Chagas’ disease. Bioorg. Med. Chem. Lett. 2006, 16, 4405–4409.
  • Fujii, N., Mallari, J.P., Hansell, E.J., Mackey, Z., Doyle, P., Zhou, Y.M., Gut, J., Rosenthal, P.J., McKerrow, J.H., Guy, R.K. Discovery of potent thiosemicarbazone inhibitors of rhodesain and cruzain. Bioorg. Med. Chem. Lett. 2005, 15, 121–123.
  • Greenbaum, D.C., Mackey, Z., Hansell, E., Doyle, P., Gut, J., Caffrey, C.R., Lehrman, J., Rosenthal, P.J., McKerrow, J.H., Chibale, K. Synthesis and structure–activity relationships of parasiticidal thiosemicarbazone cysteine protease inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi. J. Med. Chem. 2004, 47, 3212–3219.
  • Du, X., Guo, C., Hansell, E., Doyle, P.S., Caffrey, C.R., Holler, T.P., McKerrow, J.H., Cohen, F.E. Synthesis and structure–activity relationship study of potent trypanocidal thio semicarbazone inhibitors of the trypanosomal cysteine protease cruzain. J. Med. Chem. 2002, 45, 2695–2707.
  • Hall, I.H., Chen, S.Y., Barnes, B.J., West, D.X. The hypolipidemic activity of heterocyclic thiosemicarbazones, thioureas and their metal complexes in Sprague Dawley male rats. Met. Based Drugs 1999, 6, 143–147.
  • Bermejo, E., Carballo, R., Castineiras, A., Dominguez, R., Liberta, E.A., Maichle-Mossmer, C, West, D.X. Complexes of group 12 metals with 2-acetylpyridine 4N-dimethylthiosemicarbazone and with 2-acetylpyridine-N-oxide 4N-dimethylthiosemicarbazone: synthesis, structure and antifungal activity. Z. Naturforsch. 1999, 54, 777–787.
  • Pérez, J.M., Matesanz, A.I., Martín-Ambite, A., Navarro, P., Alonso, C., Souza, P. Synthesis and characterization of complexes of p-isopropyl benzaldehyde and methyl 2-pyridyl ketone thiosemicarbazones with Zn(II) and Cd(II) metallic centers. Cytotoxic activity and induction of apoptosis in Pam-ras cells. J. Inorg. Biochem. 1999, 75, 255–261.
  • Reddy, K.H., Reddy, P.S., Babu, P.R. Synthesis, spectral studies and nuclease activity of mixed ligand copper(II) complexes of heteroaromatic semicarbazones/thiosemicarbazones and pyridine. J. Inorg. Biochem. 1999, 77, 169–176.
  • Kelly, P.F., Slawin, A.Z.M., Soriano-Rama, A. Reaction of (Me3SiNSN)2S with palladium complexes; crystal structures of [PPh4]2[Pd2Br4(S3N2)] and [PPh4][PdBr2(S2N3)]. J. Chem. Soc. Dalton Trans. 1996, 53–60.
  • West, X.D., Pardhye, B.S., Sonawane, B.P. Structural and physical correlation in the biological properties of transition metal N-hetero-cyclic thiosemicarbazones and S-alkyldithiocarbazate complexes. Struct. Bonding 1991, 76, 1–50.
  • Liberta, E.A., West, X.D. Antifungal and antitumor activity of heterocyclic thiosemicarbazones and their metal complexes: current status. BioMetals. 1992, 5, 121–126.
  • West, X.D., Liberta, E.A., Padhye, B.S., Chikate, C.R., Sonawane, B.P., Kumbhar, S.A., Yerande, G.R. Thiosemicarbazone complexes of copper(II): structural and biological studies. Coord. Chem. Rev. 1993, 123, 49–71.
  • Jeyaraman, R., Avila, S. Chemistry of 3-azabicyclo[3.3.1]nonanes. Chem. Rev. 1981, 81, 149–174.
  • Lijinsky, W., Taylor, H.W. Carcinogenicity of methylated nitrosopiperidines. Int. J. Cancer 1975, 16, 318–322.
  • Cartoni, C., Figini, A., Carpi, A. [Antiarrhythmic action of certain 1,5-diphenyl-bispidin derivatives]. Ann. Ist. Super. Sanita 1968, 4, 333–335.
  • El-Subbagh, H.I., Abu-Zaid, S.M., Mahran, M.A., Badria, F.A., Al-Obaid, A.M. Synthesis and biological evaluation of certain alpha, beta-unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents. J. Med. Chem. 2000, 43, 2915–2921.
  • Aridoss, G., Amirthaganesan, S., Kumar, N.A., Kim, J.T., Lim, K.T., Kabilan, S., Jeong, Y.T. A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives. Bioorg. Med. Chem. Lett. 2008, 18, 6542–6548.
  • Karthikeyan, P., Meena Rani, A., Saiganesh, R., Balasubramanian, K.K., Kabilan, S. Synthesis of 5,6-dihydrobenz[c]acridines: a comparative study. Tetrahedron 2009, 65, 811–821.
  • Aridoss, G., Parthiban, P., Ramachandran, R., Prakash, M., Kabilan, S., Jeong, Y.T. Synthesis and spectral characterization of a new class of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones: antimicrobial, analgesic and antipyretic studies. Eur. J. Med. Chem. 2009, 44, 577–592.
  • Aridoss, G., Balasubramanian, S., Parthiban, P., Kabilan, S. Synthesis, stereochemistry and antimicrobial evaluation of some N-morpholinoacetyl-2,6-diarylpiperidin-4-ones. Eur. J. Med. Chem. 2007, 42, 851–860.
  • Aridoss, G., Balasubramanian, S., Parthiban, P., Kabilan, S. Synthesis and in vitro microbiological evaluation of imidazo(4,5-b)pyridinylethoxypiperidones. Eur. J. Med. Chem. 2006, 41, 268–275.
  • Aridoss, G., Balasubramanian, S., Parthiban, P., Kabilan, S. Synthesis and NMR spectral studies of N-chloroacetyl-2,6-diarylpiperidin-4-ones. Spectrochim. Acta. A. Mol. Biomol. Spectrosc. 2007, 68, 1153–1163.
  • Dhar, M.L., Dhar, M.M., Dhawan, B.N., Mehrotra, B.N., Ray, C. Screening of Indian plants for biological activity: I. Indian J. Exp. Biol. 1968, 6, 232–247.
  • Baliah, V., Jeyaraman, R. Synthesis of some 3-azabicyclo[3.3.1]nonane. Indian J. Chem. 1971, 9, 1020–1022.
  • Klod, S., Koch, A., Kleinpeter, E. Ab-initio quantum-mechanical GIAO calculation of the anisotropic effect of C–C and X–C single bonds—application to the 1H NMR spectrum of cyclohexane. J. Chem. Soc. Perkin. Trans. 2002, 2, 1506–1509.
  • Iriepa, I., Madrid, A.I., Galvez, E., Bellanato, J. Synthesis, structural and conformational study of 3-methyl-3-azabicyclo[3.2.1]octan-8-one and 3-methyl-3-azabicyclo[3.3.1]nonan-9-one oximes. J. Mol. Struct. 2003, 651–653, 579–583.

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