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Quantitative Structure–Activity Relationship Study on the Anti‐HIV‐1 Activity of Novel 6‐Naphthylthio HEPT Analogs
Author(s) -
Riahi Siavash,
Pourbasheer Eslam,
Dinarvand Rassoul,
Ganjali Mohammad Reza,
Norouzi Parviz
Publication year - 2009
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/j.1747-0285.2009.00843.x
Subject(s) - stepwise regression , linear regression , feature selection , quantitative structure–activity relationship , molecular descriptor , human immunodeficiency virus (hiv) , set (abstract data type) , van der waals force , regression analysis , chemistry , mathematics , stereochemistry , biology , artificial intelligence , statistics , computer science , molecule , virology , organic chemistry , programming language
The quantitative structure–activity relationship of the novel 6‐naphthylthio 1‐[(2‐hydroxyethoxy)methyl]‐6‐(phenylthio) thymine derivatives for prediction of anti‐human immunodeficiency virus type 1 activity was studied. The suitable set of the molecular descriptors was calculated and the important descriptors using the variable selections of the stepwise multiple linear regression and the genetic algorithm were selected. A comparison between the attained results indicated the superiority of the genetic algorithm over the stepwise multiple regression method in the feature‐selection. The predictive quality of the quantitative structure–activity relationship models was tested for an external set of eight compounds, randomly chosen out of 39 compounds. The genetic algorithm‐multiple linear regression model with six selected descriptors was obtained. This model, demonstrating high statistical qualities ( R 2 train = 0.925, Q 2 = 0.872, SE (%) = 1.23, F = 49.338, R 2 pred = 0.944), could predict the anti‐human immunodeficiency virus type 1 activity of the molecules with a prediction error percentage lower than 10%. The results suggest that electronegativity, the masses, and the atomic van der Waals volumes are the main independent factors contributing to the anti‐human immunodeficiency virus type 1 activity of the studied compounds.