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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

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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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