Medicinal Chemistry Research

, Volume 21, Issue 6, pp 788–795

QSAR studies on substituted 3- or 4-phenyl-1,8-naphthyridine derivatives as antimicrobial agents

  • Ponnurengam Malliappan Sivakumar
  • Geetha Iyer
  • Mukesh Doble
Original Research

DOI: 10.1007/s00044-011-9564-x

Cite this article as:
Sivakumar, P.M., Iyer, G. & Doble, M. Med Chem Res (2012) 21: 788. doi:10.1007/s00044-011-9564-x

Abstract

Quantitative Structure Activity Relationship correlating the antitubercular and antibacterial (Staphylococcus aureus and Escherichia coli) activities with the structural descriptors of reported naphthyridine derivatives was developed. The data were divided into training and test sets. The former was used to develop the regression model and the latter was used to examine the predictive capability of these models. The statistical measures such as squared correlation coefficient (r2 = 0.79–0.84), adjusted squared correlation coefficient (r2adj = 0.78–0.83) F-ratio (26.85–67.16), and cross-validation (q2 = 0.74–0.79) were found to be satisfactory for all activities and the predictions were within the 99% confidence level. The models contained atom type, thermodynamic, structural, and electrotopological descriptors which emphasized the importance of the size, shape, and the lipophilicity of the molecule.

Keywords

Quantitative structure activity relationship Genetic function approximation Antitubercular Antibacterial and molecular descriptors 

Abbreviations

QSAR

quantitative structure activity relationship

WHO

World Health Organization

SAR

structure activity relationship

MTB

M. tuberculosis

MDR-TB

multi-drug resistant M. tuberculosis

MIC

minimum inhibitory concentration

CVFF

consistent valence force field

GFA

genetic function approximation technique

LOF

lack-of-fit

LMO

leave more out method

SSE

sum of squares of the error

TSS

total sum of squares

PRESS

predicted sum of squares

ADME

absorption, distribution, metabolism, and excretion

Hf

heat of formation

Jurs-PPSA-1

sum of the solvent-accessible surface areas of all positively charged atoms

Supplementary material

44_2011_9564_MOESM1_ESM.doc (378 kb)
Supplementary material 1 (DOC 378 kb)

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Ponnurengam Malliappan Sivakumar
    • 1
  • Geetha Iyer
    • 1
  • Mukesh Doble
    • 1
  1. 1.Department of BiotechnologyIndian Institute of Technology MadrasChennaiIndia