Synthesis and evaluation of anti-tuberculosis and anti-cancer activities of hydroxynaphthoquinone derivatives
Wanthani Paengsri*[a] and Apiwat Baramee [a]* Author for corresponding; e-mail address: Wanthani Paengsri*[a] and Apiwat Baramee [a]
Volume :Vol.40 No.1 (JANUARY 2013)
Research Article
DOI:
Received: 30 August 2011, Revised: -, Accepted: 9 August 2012, Published: -
Citation: Paengsri W. and Baramee A., Synthesis and evaluation of anti-tuberculosis and anti-cancer activities of hydroxynaphthoquinone derivatives, Chiang Mai Journal of Science, 2013; 40(1): 70-76.
Abstract
Hydroxy-1,4-naphthoquinone derivatives associated with a variety of side chains have been synthesized from 2-hydroxy-1,4-naphthoquinone 1, butylamine, allylamine and selected aldehydes. Their biologically significant activities, anti-mycobacterium tuberculosis (H37Ra strain), anti-cancer (MCF7-breast cancer and NCI-H187-small cell lung cancer) were studied and reported. It was found that (2E,4E)-1,4-dioxo-1,4-dihydronaphthalen-2-yl-5(benzo[d][1,3]dioxol-5-yl)penta-2,4-dienoate 6 showed significant anti-MCF7 and anti-NCI-H187 activities with IC50 value at 3.84 µg/mL and 2.24 µg/mL and was found non-cytotoxic. In addition, 2-((allylamino)(phenyl)methyl)-3-hydroxynaphthalene-1,4-dione 2f also showed similar bioactivities to those of compound 6 and it showed anti-TB activity with MIC value 25 µg/mL however it was found to display cytotoxic activity against Vero cells.