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Vol. 31 No. 1 (2019): Vol 31 Issue 1

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Synthesis and Antimicrobial Activities of Iminothioether Linkers on Cyclopenta[a]phenanthrene Derivatives

https://doi.org/10.14233/ajchem.2019.21519
Balasaheb P. Pagar
Post Graduate Department of Chemistry, K.S.K.W. Arts, Science & Commerce College, Uttamnagar, CIDCO, Nashik-422008, India

Corresponding Author(s) : Balasaheb P. Pagar

pagarbp77@gmail.com

Asian Journal of Chemistry, Vol. 31 No. 1 (2019): Vol 31 Issue 1

Abstract

The reaction of methylbenzo[h][1,6]naphthyridine (1) with thiourea yield 4-chloro-12-methyl-16,17- dihydro-15-thia-6,11-diaza-cyclopenta[a]phenanthrene-7-thiol (2). The chemistry of compound 2 is explored to obtained iminothioether derivatives (3a-h) in good yields. The structures of newly synthesized compounds were confirmed by spectral data and elemental analysis. The antimicrobial activity of newly synthesized compounds were studied against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Pseudomonas aeroginosa, Proteus valgaris, Bacillus cereus, Streptococcus sp. and Bacillus megaterium by the agar well diffusion method. Compounds 3d, 3f and 3h showed moderate antimicrobial activity.

Keywords

Benzo[h][1,6]naphthyridine cyclopenta[a]phenanthrene Antimicrobial
Pagar, B. P. (2018). Synthesis and Antimicrobial Activities of Iminothioether Linkers on Cyclopenta[a]phenanthrene Derivatives. Asian Journal of Chemistry, 31(1), 79–82. https://doi.org/10.14233/ajchem.2019.21519
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References
  1. A.K. Munusamy, M.S. Kumar, P.D. Subramanian and P. Rajendran, J. Chin. Chem. Soc., 64, 138 (2017); https://doi.org/10.1002/jccs.201600196.
  2. K. Ramkumar, E. Serrao, S. Odde and N. Neamati, Med. Res. Rev., 30, 890 (2010); https://doi.org/10.1002/med.20194.
  3. B.A. Johns, J.G. Weatherhead, S.H. Allen, J.B. Thompson, E.P. Garvey, S.A. Foster, J.L. Jeffrey and W.H. Miller, Bioorg. Med. Chem. Lett., 19, 1807 (2009); https://doi.org/10.1016/j.bmcl.2009.01.089.
  4. J.Y. Melamed, M.S. Egbertson, S. Varga, J.P. Vacca, G. Moyer, L. Gabryelski, P.J. Felock, K.A. Stillmock, M.V. Witmer, W. Schleif, D.J. Hazuda, Y. Leonard, L. Jin, J.D. Ellis and S.D. Young, Bioorg. Med. Chem. Lett., 18, 5307 (2008); https://doi.org/10.1016/j.bmcl.2008.08.038.
  5. M.S. Egbertson, H.M. Moritz, J.Y. Melamed, W. Han, D.S. Perlow, M.S. Kuo, M. Embrey, J.P. Vacca, M.M. Zrada, A.R. Cortes, A. Wallace, Y. Leonard, D.J. Hazuda, M.D. Miller, P.J. Felock, K.A. Stillmock, M.V. Witmer, W. Schleif, L.J. Gabryelski, G. Moyer, J.D. Ellis, L. Jin, W. Xu, M.P. Braun, K. Kassahun, N.N. Tsou and S.D. Young, Bioorg. Med. Chem. Lett., 17, 1392 (2007); https://doi.org/10.1016/j.bmcl.2006.11.080.
  6. G. Falardeau, H. Lachance, A. St-Pierre, C.G. Yannopoulos, M. Drouin, J. Bédard and L. Chan, Bioorg. Med. Chem. Lett., 15, 1693 (2005); https://doi.org/10.1016/j.bmcl.2005.01.050.
  7. L. Chan, H. Jin, T. Stefanac, J.F. Lavallee, G. Falardeau, W. Wang, J. Bedard, S. May and L. Yuen, J. Med. Chem., 42, 3023 (1999); https://doi.org/10.1021/jm9902483.
  8. A.M. Thompson, C.J.C. Connolly, J.M. Hamby, S. Boushelle, B.G. Hartl, A.M. Amar, A.J. Kraker, D.L. Driscoll, S.J. Steinkampf, S.J. Patmore, P.W. Vincent, B.J. Roberts, W.L. Elliott, W. Klohs, W.R. Leopold, H.D.H. Showalter and W.A. Denny, J. Med. Chem., 43, 4200 (2000); https://doi.org/10.1021/jm000161d.
  9. S. Vanlaer, A. Voet, C. Gielens, M. De Maeyer and F. Compernolle, Eur. J. Org. Chem., 643 (2009); https://doi.org/10.1002/ejoc.200800972.
  10. (a) E.-S. Badawey and T. Kappe, J. Heterocycl. Chem., 32, 1003 (1995); https://doi.org/10.1002/jhet.5570320355. (b) E.-S. Badawey, J. Heterocycl. Chem., 32, 229 (1996); https://doi.org/10.1002/jhet.5570330202.
  11. T. Ichikawa, J.C. Lamb, P.I. Christensson, B. Hartly-Asp and J.T. Issacs, Cancer Res., 52, 3022 (1992).
  12. S.C. Kuo, H.Z. Lee, J.P. Juang, Y.T. Lin, T.S. Wu, D. Lednicer, J.J. Chang, K.D. Paull and C.M. Lin, J. Med. Chem., 36, 1146 (1993); https://doi.org/10.1021/jm00061a005.
  13. Q. Liu, J.W. Chang, J. Wang, S.A. Kang, C.C. Thoreen, A. Markhard, W. Hur, J. Zhang, T. Sim, D.M. Sabatini and N.S. Gray, J. Med. Chem., 53, 7146 (2010); https://doi.org/10.1021/jm101144f.
  14. Q. Liu, J. Wang, S.A. Kang, C.C. Thoreen, T. Ahmed, D.M. Sabatini, W. Hur and N.S. Gray, J. Med. Chem., 54, 1473 (2011); https://doi.org/10.1021/jm101520v.
  15. R.B. Toche, B.P. Pagar, R.R. Zoman, G.B. Shinde and M.N. Jachak, Tetrahedron, 66, 5204 (2010); https://doi.org/10.1016/j.tet.2010.04.085.
  16. R.B. Toche, B.K. Ghotekar, M.A. Kazi and M.N. Jachak, Monatsh. Chem., 140, 235 (2009); https://doi.org/10.1007/s00706-008-0062-x.
  17. R.B. Toche, B.K. Ghotekar, D.B. Kendre, M.A. Kazi and M.N. Jachak, J. Heterocycl. Chem., 45, 1711 (2008); https://doi.org/10.1002/jhet.5570450624.
  18. R.B. Toche, B.K. Ghotekar, M.A. Kazi, S.P. Patil and M.N. Jachak, Scholarly Res. Exch., Article ID 434329 (2008); https://doi.org/10.3814/2008/434329.
  19. B.K. Ghotekar, M.A. Kazi, M.N. Jachak and R.B. Toche, Can. J. Chem., 86, 1070 (2008); https://doi.org/10.1139/v08-155.
  20. R.B. Toche, B.K. Ghotekar, M.A. Kazi, D.B. Kendre and M.N. Jachak, Tetrahedron, 63, 8157 (2007); https://doi.org/10.1016/j.tet.2007.05.123.
  21. R.V. Rote, D.P. Shelar, S.R. Patil, S.S. Shinde, R.B. Toche and M.N. Jachak, J. Fluoresc., 21, 453 (2011); https://doi.org/10.1007/s10895-010-0704-3.
  22. E.-S. Badawey and T. Kappe, Eur. J. Med. Chem., 32, 815 (1997); https://doi.org/10.1016/S0223-5234(99)80067-1.
  23. E.-S.A.M. Badawey, J. Heterocycl. Chem., 33, 229 (1996); https://doi.org/10.1002/jhet.5570330202.
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