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Synthesis and in vitro antimicrobial and antitumor activity of some nitrogen heterocycles

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Abstract

5-Phenyl-2-[(3,4,5-trimethoxybenzylidene)hydrazino]-thiazole and 3-[(3,4,5-trimethoxybenzylidene)amino]-4-oxoimidazolidin-2-thione were prepared by cyclization of 1-[(3,4,5-trimethoxybenzyliden)amino]-thiourea with phenacyl bromide and ethyl chloroacetate in the presence of fused sodium acetate. Acetylation of the synthesized compounds with acetic anhydride gave corresponding N-acetyl derivatives. Condensation of the synthesized thione with aromatic aldehydes yielded two 3-substituted 5-arylidene-4oxo-imidazolidin-2-thiones. Acetylation of the latter compounds with acetic anhydride afforded the corresponding N-acetyl-4-oxo-imidazolidin-2-thiones. Some of the synthesized compounds exhibited antimicrobial activity. The cytotoxic activity of the prepared thiazole and imidazolidin-2-thione derivatives was studied on several tumor cell lines.

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References

  1. Wilson, L.J., Li, M., and Portlock, D.E., Tetrahedron Lett., 1998, vol. 39, no. 29, pp. 5135–5138.

    Article  CAS  Google Scholar 

  2. Belai, I., Tetrahedron Lett., 2003, vol. 44, no. 40, pp. 7475–7477.

    Article  CAS  Google Scholar 

  3. Brouilette, W.J., Jestkov, V.P., Brown, M.L., Akhtar,M.S., Delorey, T.M., and Brawn, G.B., J. Med. Chem., 1994, vol. 37, pp. 3289–3293.

    Article  Google Scholar 

  4. Erik, C.S., Ottosen, R., Petersen, H.J., Bjorking, F., Latini, S., Hjarnaa, V., Bramm, E., and Binderup, L., Bioorg. Med. Chem. Lett., 1997, vol. 7, pp. 3095–3100.

    Article  Google Scholar 

  5. Hjarnaa, P.J., Jonsson, E., Latini, S., Dhar, S., Larsson, R., Bramm, E., Skov, T., and Binderup, L., Cancer Res., 1999, vol. 59, pp. 5751–5757.

    CAS  PubMed  Google Scholar 

  6. Olsen, L.S., Hijamaa, P.J., Latini, S., Holm, P.K., Larsson, R., Bramm, E., Binderup, I., and Madsen, M.W., Inc. Cancer, 2004, vol. 3, pp. 98–105.

    Google Scholar 

  7. Mader, M.M., Curr. Opin. Drug Discov. Devel., 2005, vol. 8, pp. 613–618.

    CAS  PubMed  Google Scholar 

  8. Ibrahim, H.K., Hasanen, J.A., Zein, M.A., and ElDeen, I.M., Mens Agitat., 2008, vol. 3, pp. 59–72.

    CAS  Google Scholar 

  9. Aboubshit, S.A. and Aboubshit, H.A., J. Chem. Pharm. Res., 2012, vol. 4(1), pp. 568–579.

    Google Scholar 

  10. Abd El-Moneim, M., IOSR JAC, 2014, vol. 7, no. 1, pp. 67–76.

    Article  CAS  Google Scholar 

  11. El-Sakka, S., Mens Agitat., 2008, vol. 2, pp. 57–68.

    Google Scholar 

  12. Schelz, Z., Molnar, J., and Hohmann, J., Fitoterapia, 2006, vol. 77, no. 4, pp. 279–285.

    Article  CAS  PubMed  Google Scholar 

  13. National Committee for Clinical Laboratory Standards. Performance Standards for Antimicrobial Susceptibility Testing, Informational Supplement M100. S13, 12th ed., NCCLS: Wayne, PA,USA, 2003.

  14. Gillespie, S.H., Antimicrobial Susceptibility in Medical Microbiology, Illustrated, London: Butterworth Heinemann, 1994, pp. 234–247.

    Google Scholar 

  15. Chatterjee, S. and Das, S.N., Ind. J. Pharmacol., 1996, vol. 28, pp. 116–119.

    CAS  Google Scholar 

  16. Mosmann, T., J. Immunol. Methods, 1983, vol. 65, pp. 55–63.

    Article  CAS  PubMed  Google Scholar 

  17. Vijayen, P., Raghu, C., Ashok, G., Dhanaraj, S.A., and Suresh, B., Indian J. Med. Res., 2004, vol. 120, no. 1, pp. 9–24.

    Google Scholar 

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Correspondence to A. I. El-Shenawy.

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El-Shenawy, A.I. Synthesis and in vitro antimicrobial and antitumor activity of some nitrogen heterocycles. Russ J Bioorg Chem 42, 100–105 (2016). https://doi.org/10.1134/S1068162016010040

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  • DOI: https://doi.org/10.1134/S1068162016010040

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