6-Allyl-3-(4-Methoxybenzyl-8-Methoxy-3,4-Dihydro-2h-Benzo[e][1,3]Oxazine and 4-Allyl-2-Methoxy-6-(4-Methoxybenzyl)Aminomethylphenol: Synthesis and cytotoxicity test on MCF-7 cells

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Abstract

The aim of the present study is to synthesize new benzoxazine and aminomethyl derivatives of eugenol, and to examine the cytotoxicity of the derivatives on MCF-7 cells. 6-Alyl-3-(4-methoxybenzyl-8-methoxy-3,4-dihydro-2H-benzo[e]1,3 oxazine was prepared by Mannich Reaction between eugenol, formaldehyde, and 4-methoxybenzylamine in methanol. 4-Allyl-2-methoxy-6-(4-methoxybenzyl)aminomethylphenol was prepared by hydrolysis of the benzoxazine with hydrochloric acid in 1-propanol followed by treatment with ammonia. The obtained compounds were subjected to cytotoxicity study using MTT assay and calculate the percent of cell viability. As the results, 6-allyl-3-(4-methoxybenzyl-8-methoxy-3,4-dihydro-2H-benzo[e]1,3 oxazine was obtained in 94% yield, while 4-allyl-2-methoxy-6-(4-methoxybenzyl)aminomethylphenol was obtained in 87% yield. The obtained LC50 values of the tested compounds on MCF-7 cancer cell line are respectively 22.5±0.20 and 24.6±0.92 μg/ml.

Original languageEnglish
Pages (from-to)387-391
Number of pages5
JournalInternational Journal of Pharmaceutical and Clinical Research
Volume8
Issue number5
Publication statusPublished - 2016

Keywords

  • Aminomethyl
  • Benzoxazines
  • Cytotoxicity
  • Eugenol
  • MCF-7

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