Cobalt mediated ring contraction reaction of lapachol and initial antibacterial evaluation of naphthoquinones derived from lapachol
Medicinal Chemistry Research
Department of Chemistry, Indian Institute of Technology, Madras, Chennai 600 036, India; Department of Organic Chemistry, University of Yaounde 1, BP 812, Yaounde, Cameroon; Department of Biochemistry, University of Dschang, BP 67, Dschang, Cameroon; Department of Chemistry, University of Buea, 63, Buea, Cameroon; Department of Chemistry, University of New Brunswick, Fredericton, NB E3B 5A3, Canada; Department of Plant Science, Faculty of Agricultural and Biological Science, Pretoria 0002, South Africa
The synthesis of 2-hydroxy-2-(3-methylbut- 2-enyl)-2H-indene-1,3-dione 3, from lapachol which involves a ring contraction via the Hooker intermediate 1,2-dihydroxy-2-(3-methylbut-2-en-1-yl)-3-oxo-2,3-dihydro- 1H-indene-1- carboxylic acid 2 is described. Different pyranonaphthoquinone derivatives, obtained in our previous synthetic work, were screened for antimycobacterial (Mycobacterium tuberculosis) activity and against resistant strains of Gram-positive (Bacillus cereus and Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. The results indicated significant activity of all the tested samples against M. tuberculosis and only moderate activity against the Gram-positive and Gram-negative bacteria. © Springer Science+Business Media, LLC 2011.
1 (2,3,4,9 tetrahydro 4,9 dioxonaphtho[2,3 b]furany 2 yl) 1 methylethyl nitrate; 1,4 dihydro 3 hydroxy 1,4 dioxo 2 naphthaleneacetaldehyde; 2 (1 methylethenyl) 2,3 dihydronaphtho[2,3 b]furan 4,9 dione; 2 (1' methylethenyl)naphtho[2,3 b]furan 4,9 dione; 2 (3 hydroxy 1,4 dioxo 1,4 dihydronaphthalene 2 yl)vinyl acetate; 2 acetyl furanonapthoquinone; 2 hydroxy 2 (3 methylbut 2 enyl) 2h indene 1,3 dione; beta lapachone; cobalt; gentamicin; isoniazid; lapachol; naphthoquinone; unclassified drug; antibacterial activity; article; Bacillus cereus; bacterial strain; chemical reaction; controlled study; drug screening; Escherichia coli; minimum inhibitory concentration; Mycobacterium tuberculosis; nonhuman; ring contraction reaction; Staphylococcus aureus