Synthesis and evaluation of anti-tuberculosis and anti-cancer activities of hydroxynaphthoquinone derivatives

• Main Authors: Wanthani Paengsri, Apiwat Baramee
• Format: Journal
• Published: 2018
• Subjects: Biochemistry, Genetics and Molecular Biology; Chemistry; Materials Science; Mathematics; Physics and Astronomy
• Online Access: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84873359735&origin=inward; http://cmuir.cmu.ac.th/jspui/handle/6653943832/52273
• Institution: Chiang Mai University

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.