Three-dimensional quantitative structure–activity relationships study on HIV-1 reverse transcriptase inhibitors in the class of dipyridodiazepinone derivatives, using comparative molecular field analysis

Pungpo, Pornpan; Hannongbua, Supa

doi:10.1016/s1093-3263(00)00053-x

Cited by 30 publications

(23 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Comparative Molecular Field Analysis (CoMFA) was applied on dipyridodiazepinone derivatives [18], which are active against wild-type (WT) and mutant-type (Y181C) HIV-1 reverse transcriptase. QSAR analysis of anti-HIV drugs was performed on phosphoramidate derivatives [19] using Hansch analysis.…”

Section: Introductionmentioning

confidence: 99%

Classical QSAR Modeling of HIV‐1 Reverse Transcriptase Inhibitor 2‐Amino‐6‐arylsulfonylbenzonitriles and Congeners

Leonard

Roy

2004

QSAR Comb. Sci.

View full text Add to dashboard Cite

Full PaperConsidering the recent interests in the development of novel and potent non-nucleoside reverse transcriptase inhibitors for the treatment of HIV-1 infection, anti-HIV-1 activity (assayed in MT-4 cell line) and HIV-1 reverse transcriptase (RT) binding affinity of 2-amino-6-arylsulfonylbenzonitriles and their thio and sulfinyl congeners (Chan et al., J. Med. Chem., 2001, 44, 1866 ± 1882 have been modeled using classical Quantitative Structure-Activity Relationship (QSAR) tools in an attempt to explore the quantitative contribution pattern of different substituents in the aryl ring to the activities. Different physicochemical parameters like hydrophobicity (p), electronic (Hammett s) and steric (molar refractivity MR) terms have been used along with appropriate indicator and/or integer variables to develop linear free energy related (LFER) model. Additionally, electrostatic potential point charges at different common atoms of the molecules calculated from AM1 optimized energy minimized geometry have also been tried as predictor variables. The models generated were of acceptable statistical quality and predictive potential. The results show that for both response variables, presence of sulfone moiety contributes significantly to the activities. Further, molar refractivity of meta substituents plays a significant role in both the cases: second meta substituents potentiate the activities probably due to enhanced binding (presumably through dispersion interaction) of the ligand with the binding site. Again, presence of meta-trifluoromethyl group at the aryl ring is detrimental for both the activities. Additionally, the anti-HIV-1 model shows negative contribution of the steric parameter of para substituents and positive contribution of the ortho-methoxy group.

show abstract

Section: Introductionmentioning

confidence: 99%

Classical QSAR Modeling of HIV‐1 Reverse Transcriptase Inhibitor 2‐Amino‐6‐arylsulfonylbenzonitriles and Congeners

Leonard

Roy

2004

QSAR Comb. Sci.

View full text Add to dashboard Cite

show abstract

“…This model showed good correlation coefficient (R) of 0.875 between descriptors (logP, logP 2 , and IR) and HIV-1 protease inhibitory activity. This model also indicates statistical significance > 99.9% with F-value F (3,44) = 47.86. showed that the presence of -(CH 2 ) 2 C 6 H 5 group at sixth position of dihydropyranone nucleus is essential for better activity.…”

Section: Qsar Models Development and Validationmentioning

confidence: 68%

“…Its central role in virus maturation makes protease is a prime target for anti-HIV-therapy 2 . QSAR analyses of HIV-1 reverse transcriptase inhibitors 3 , HIV-1 protease inhibitors [4][5][6][7] , and HIV-1 integrase inhibitors 8,9 were reported. The present group of authors has developed a few quantitative structure-activity relationship models to predict biological activity of different group of compounds [10][11][12][13][14][15][16] .…”

Section: Introductionmentioning

confidence: 99%

Prediction of HIV-1 protease inhibitory activity of 4-hydroxy-5,6-dihydropyran-2-ones: QSAR study

Ravichandran

Agrawal

2010

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

“…The 2D QSAR studies have been carried out for anti-HIV activities of different groups of compounds [9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] . Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) have also been carried out for anti-HIV activity of a given set of molecules in rational drug design and its related applications [24][25][26][27][28][29][30][31][32][33][34][35][36][37] .…”

Section: Research Articlementioning

confidence: 99%

Designing hypothesis of substituted benzoxazinones as HIV-1 reverse transcriptase inhibitors: QSAR approach

Veerasamy

Subramaniam

Chean

et al. 2011

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

Three-dimensional quantitative structure–activity relationships study on HIV-1 reverse transcriptase inhibitors in the class of dipyridodiazepinone derivatives, using comparative molecular field analysis

Cited by 30 publications

References 26 publications

Classical QSAR Modeling of HIV‐1 Reverse Transcriptase Inhibitor 2‐Amino‐6‐arylsulfonylbenzonitriles and Congeners

Classical QSAR Modeling of HIV‐1 Reverse Transcriptase Inhibitor 2‐Amino‐6‐arylsulfonylbenzonitriles and Congeners

Prediction of HIV-1 protease inhibitory activity of 4-hydroxy-5,6-dihydropyran-2-ones: QSAR study

Designing hypothesis of substituted benzoxazinones as HIV-1 reverse transcriptase inhibitors: QSAR approach

Contact Info

Product

Resources

About