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Design, synthesis, and anticancer evaluation of some novel thiourea, carbamimidothioic acid, oxazole, oxazolidine, and 2-amino-1-phenylpropyl-2-chloroacetate derived from L-norephedrine

Russian Journal of Bioorganic Chemistry volume 42, pages 434–440 (2016)Cite this article

Abstract

A novel series of thiourea, carbamimidothioic acid, 4, 5-dihydrooxazole-2-thiol, oxazolidine-2thine, and 2-amino-1-phenylpropyl-2-chloroacetate derivatives was designed and synthesized using 2-amino-1-phenylpropan-1-ol (L-norephedrine) as a strategic starting material. The structures of the newly synthesized compounds were established by elemental analyses, IR, and 1H NMR and 13C NMR spectral data. The compounds were evaluated for their in vitro anticancer activity against various cancer cell lines. The corresponding acetamide, carbamimidothioic acid, and 2-2-amino-1-phenylpropyl-2-chloroacetate derivatives showed almost the same activity as the standard drug doxorubicin against human breast cancer cell line (MCF-7). Also, the acetamide and 2-thioxoimidazolidin-4-one derivatives exhibited higher activity than the reference drug doxorubicin against human colon cancer cell line (HCT 116).

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References

  1. Gupta, S.P., Chem. Rev., 1994, vol. 94, pp. 1507–1551.

    CAS  Article  Google Scholar 

  2. Keri, G. and Ullrich, A., Cancer as a communication disorder, in Molecular Pathomechanisms and New Trends in Drug Research, Keri, G. and Toth, I., Eds., London: Taylor and Francis, 2003, pp. 227–248.

    Google Scholar 

  3. Vega-Pérez, J.M., Periñán, I., Argandoña, M., Vega-Holm, M., Palo-Nieto, C., Burgos-Morón, E., López-Lázaro, M., Vargas, C., Nieto, J.J., and Iglesias-Guerra, F., Eur. J. Med. Chem., 2012, vol. 58, pp. 591–612.

    Article  PubMed  Google Scholar 

  4. Yao, J., Chen, J., He, Z., Sun, W., and Xu, W., Bioorg. Med. Chem., 2012, vol. 20, pp. 2923–2929.

    CAS  Article  PubMed  Google Scholar 

  5. Shantharam, C.S., Suyoga, V.D.M., Suhas, R., Sridhara, M.B., and Channe, G.D., Eur. J. Med. Chem., 2013, vol. 60, pp. 325–332.

    CAS  Article  PubMed  Google Scholar 

  6. Yang, W., Hu, Y., Yang, Y.S., Zhang, F., Zhang, Y.B., Wang, X.L., Tang, J.F., Zhong, W.Q., and Zhu, H.L., Bioorg. Med. Chem., 2013, vol. 21, pp. 1050–1063.

    CAS  Article  PubMed  Google Scholar 

  7. Keche, A.P., Hatnapure, G.D., Tale, R.H., Rodge, A.H., and Kamble, V.M., Bioorg. Med. Chem., 2012, vol. 22, pp. 6611–6615.

    CAS  Article  Google Scholar 

  8. Burgeson, J.R., Moore, A.L., Boutilier, J.K., Cerruti, N.R., Gharaibeh, D.N., Lovejoy, C.E., Amberg, S.M., Hruby, D.E., Tyavanagimatt, S.R., Allen, R.D., and Daisar, D., Bioorg. Med. Chem. Lett., 2012, vol. 22, pp. 4263–4272.

    CAS  Article  PubMed  Google Scholar 

  9. Kazimierczuk, Z., Chalimoniuk, M., Laudy, A.E., Moo-Puc, R., Cedillo-Rivera, R., Starosciak, B.J., and Chrapusta, S.J., Arch. Pharm. Res., 2010, vol. 33, pp. 821–830.

    CAS  Article  PubMed  Google Scholar 

  10. Al-Dosari, M.S., Ghorab, M.M., Alsaid, M.S., Nissan, Y.M., and Ahmed, A.B., Eur. J. Med. Chem., 2013, vol. 16, pp. 373–383.

    Article  Google Scholar 

  11. Fang-Bin, H., Ze-Mei, G., Tie-Ming, Ch., and RunTao, L., SYNLETT, 2009, vol. 4, pp. 0648–0650.

    Google Scholar 

  12. Kumar, V., Kumar, A., Sureshbabu, V.V., and Chimni, S.S., Med. Chem., 2014, vol. 14, pp. 910–920.

    CAS  Google Scholar 

  13. Sen-Lin, W., Yu-Jun, S., Hai-Bing, H., Yu, L., Yang, L., and Hong, D., Chinese Chem. Lett., 2015, vol. 26, pp. 672–674.

    Article  Google Scholar 

  14. Tian, Y., Jin, J., Wang, X., Hu, J., Xiao, Q., Zhou, W., Chen, X., and Yin, D., Eur. J. Med. Chem., 2014, vol. 85, pp. 1–15.

    CAS  Article  PubMed  Google Scholar 

  15. Martins, P., Jesus, J., Santos, S., Raposo, L.R., RomaRodrigues, C., Viana Baptista, P., and Fernandes, A.R., Molecules, 2015, vol. 20, pp. 16852–16891.

    CAS  Article  PubMed  Google Scholar 

  16. Kumar, V., Mudgal, M.M., Rani, N., Jha, A., Jaggi, M., Singh, A.T., Sanna, V.K., Singh, P., Sharma, P.K., Irchhaiya, R., and Burman, A.C., J. Enzy. Inhib. Med. Chem., 2009, vol. 24, pp. 763–770.

    CAS  Article  Google Scholar 

  17. Rodriguez-Fernandez, E., Manzano, J.L., Benito, J.J., Hermosa, R., Monte, E., and Criado, J.J., J. Inorg. Biochem., 2005, vol. 99, pp. 1558–1572.

    CAS  Article  PubMed  Google Scholar 

  18. Rauf, M.K., Ebihara, M., and Imtiaz-ud-Din, B.A., Acta. Cryst. Sect. E Online, 2012, vol. 68, p. o119.

    CAS  Article  Google Scholar 

  19. Koca, I., Özgür, A., Coşkun K.A., and Tutar, Y., Bioorg. Med. Chem., 2013, vol. 21, pp. 3859–3865.

    CAS  Article  PubMed  Google Scholar 

  20. Lv, P.C., Li, H., Sun, J., Zhou, Y., and Zhu, H., Bioorg. Med. Chem., 2010, vol. 18, pp. 4606–4614.

    CAS  Article  PubMed  Google Scholar 

  21. Crank, G., Neville, M., and Ryden, R., J. Med. Chem., 1973, vol. 16, pp. 1402–1405.

    CAS  Article  PubMed  Google Scholar 

  22. Jianwen, Y., Zuopeng, H., Jing, C., Daquan, C., Wei, S., and Wenfang, X., Chin. J. Chem., 2012, vol. 30, pp. 2423–2430.

    Article  Google Scholar 

  23. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J.T., Bokesch, H., Kenney, S., and Boyd, M.R., J. Natl. Cancer Inst., 1990, vol. 82, pp. 1107–1112.

    CAS  Article  PubMed  Google Scholar 

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Authors and Affiliations

  1. Department of Pharmacognosy, College of Pharmacy, Prince Sattam Bin Abdulaziz University, Al-Kharj, Saudi Arabia

    Maged S. Abdel-Kader

  2. Department of Pharmacognosy, College of Pharmacy, Alexandria University, Alexandria, Egypt

    Maged S. Abdel-Kader

  3. Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh, 11451, Saudi Arabia

    Mostafa M. Ghorab, Mansour S. Alsaid & Saleh I. Alqasoumi

  4. Department of Drug Radiation Research, National Center for Radiation Research and Technology, P.O. Box 29, Nasr City, Cairo, Egypt

    Mostafa M. Ghorab

Authors
  1. Maged S. Abdel-Kader
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  2. Mostafa M. Ghorab
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  3. Mansour S. Alsaid
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  4. Saleh I. Alqasoumi
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Correspondence to Mostafa M. Ghorab.

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Abdel-Kader, M.S., Ghorab, M.M., Alsaid, M.S. et al. Design, synthesis, and anticancer evaluation of some novel thiourea, carbamimidothioic acid, oxazole, oxazolidine, and 2-amino-1-phenylpropyl-2-chloroacetate derived from L-norephedrine. Russ J Bioorg Chem 42, 434–440 (2016). https://doi.org/10.1134/S1068162016040026

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  • DOI: https://doi.org/10.1134/S1068162016040026

Keywords

  • thiourea carbamimidothioic acid
  • oxazole
  • oxazolidine
  • 2-amino-1-phenylpropyl-2-chloroacetate
  • anticancer activity