ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
Study of physicochemical properties-antitubercular activity relationship of naphthalene-1,4-dione analogs: A QSAR approach
Revathi A. Gupta, Arun Kumar Gupta, Love Kumar Soni, and Satish G. Kaskhedikar
Molecular Modelling Study Group, CADD Laboratory, Drug Design and Discovery, Department of Pharmacy, Shri G. S. Institute of Technology and Science, 23 Park Road, Indore, 452003, M.P., India
Received: 1 December 2008 Revised: 23 May 2009 Accepted: 27 May 2009
Abstract: Enduring pandemic nature of tuberculosis urges to explore novel antimycobacterial agents with different mechanism of actions.
Plant containing 1,4-naphthoquinone derivatives showed promising antitubercular activity with novel mode of action and their
synthetic/semi-synthetic derivatives devoid of toxicity. Structural requirements of naphthalene-1,4-dione derivatives towards
antitubercular activity and cytotoxicity were explored using a mathematical model in order to understand their physicochemical
parameters. A quantitative structure activity relationship study furnished some important structural insights for antitubercular
activity, i.e. average connectivity index, information content index of neighborhood symmetry, aromatic ratio, and path/walk
3 Randic shape index. Similarly it also provides drivers for the cytotoxicity of compounds. These drivers will be helpful
in further development of safer and potent 1,4-naphthoquinone derivatives.
Keywords: naphthalene-1,4-diones - QSAR - antitubercular activity - cytotoxicity
Full paper is available at www.springerlink.com.
Chemical Papers 63 (6) 723–730 (2009)