Synthesis and Activity Analysis of 3-(10-Bromodecyl)-5-isopropyl-2-methyl-1,4-benzoquinone: In-silico Approach

DOI

10.2991/icoh-17.2018.24How to use a DOI?

Keywords

thymoquinone, lipophilicity, bromo alkylation, anticancer, cytochrome protein

Abstract

The 3-(10-bromodecyl)-5-isopropyl-2-methyl-1,4-benzoquinone (1) have been synthesized and structurally characterized by mass spectrometer (LC-MS), FT-IR, 1H-NMR and 13C-NMR spectra. The synthesis was carried out by refluxed Thymoquinone (TQ) with bromoundecanoic acid in the presence of acetonitrile:water (2:1 v/v) for 1.5 h. Purification of the products was conducted by open-column chromatography. Determination of product is mainly observed from C-Br stretching at 562-563 cm-1 by FT-IRand the chemical shift at = 3.4 ppm (1H-NMR) and 33-34 ppm (13C-NMR). In addition, = 1.38-3.05 ppm (1H-NMR) and 21-32 ppm (13C-NMR) considered as aliphatic alkane which substituted at C-6 onThymoquinone ring. Analysis using LC-MS showed the molecular weight of 1is 382.96 g/mol. The yield of 1is 12.09% as brownish-yellow liquid. Activity test of 1against the cytochrome protein (CYP) as macromolecule model revealed a good fit with IC50 1.23 mg/mL lower than TQ (36.11 mg/mL). It is showed that compound 1 exhibit anticancer activity better than TQ.

Copyright

© 2018, the Authors. Published by Atlantis Press.

Open Access

This is an open access article distributed under the CC BY-NC license (http://creativecommons.org/licenses/by-nc/4.0/).

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TY  - CONF
AU  - Novia Eka Setyatama
AU  - Siti Mariyah Ulfa
AU  - Hideki Okamoto
PY  - 2017/07
DA  - 2017/07
TI  - Synthesis and Activity Analysis of 3-(10-Bromodecyl)-5-isopropyl-2-methyl-1,4-benzoquinone: In-silico Approach
BT  - Proceedings of the 1st International Conference in One Health (ICOH 2017)
PB  - Atlantis Press
SP  - 118
EP  - 123
SN  - 2468-5739
UR  - https://doi.org/10.2991/icoh-17.2018.24
DO  - 10.2991/icoh-17.2018.24
ID  - Setyatama2017/07
ER  -