TY - JOUR
T1 - 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
T2 - Synthesis and cytotoxicity test on MCF-7 cells
AU - Rudyanto, Marcellino
AU - Widiandani, Tri
AU - Syahrani, Achmad
N1 - Publisher Copyright:
© 2016, International Journal of Pharmaceutical and Clinical Research. All rights reserved.
PY - 2016
Y1 - 2016
N2 - 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.
AB - 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.
KW - Aminomethyl
KW - Benzoxazines
KW - Cytotoxicity
KW - Eugenol
KW - MCF-7
UR - http://www.scopus.com/inward/record.url?scp=84968782917&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:84968782917
SN - 0975-1556
VL - 8
SP - 387
EP - 391
JO - International Journal of Pharmaceutical and Clinical Research
JF - International Journal of Pharmaceutical and Clinical Research
IS - 5
ER -