Exploring 3D-QSAR for Ketolide Derivatives as Antibacterial Agents Using CoMFA and CoMSIA

Song, Qiuling; Sun, Ping-Hua; Chen, Wei-Min

doi:10.2174/157018010790596641

Cited by 12 publications

(12 citation statements)

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“…The novel ketolides that possessed 4-5 carbon atoms alkyl side chain, such as 11e-k, exhibited somewhat increased potencies Electron-withdrawing groups or hydrogen bond do nor groups will improve activity Electron-withdrawing groups will improve activity Figure 2 Structure-activity relationships of ketolides from 3D-QSAR study. 36 Novel ketolides bearing an aryltetrazolyl-substituted alkyl side chain Q-L Song et al toward all of the erythromycin-susceptible S. aureus; 11n, 11p and 11q showed the equivalent potencies compared with telithromycin against the erythromycin-susceptible S. aureus. Compounds 11a, 11e-i, 11n displayed some extent increased potencies against erythromycinresistant S. aureus 5677; 11d, 11j, 11k, 11p, and 11q showed the equivalent potencies compared with telithromycin against S. aureus 5677.…”

Section: Antibacterial Activitymentioning

confidence: 99%

“…36 The structure-activity relationship revealed by CoMFA and CoMSIA models indicated that the hydrophilic group at the first heterocyclic ring of side chain in ketolides would increase the potency (Figure 2). In an effort to find novel ketolides with extended antibacterial spectrum and improved activity, we designed the novel derivatives by replacing the imidazole ring in telithromycin with a more hydrophilic tetrazole ring.…”

Section: Introductionmentioning

confidence: 99%

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Design, synthesis and antibacterial activity of novel ketolides bearing an aryltetrazolyl-substituted alkyl side chain

et al. 2011

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A set of 17 novel ketolides bearing an aryltetrazolyl-substituted alkyl side chain were synthesized and evaluated for their antibacterial activities, which the aryltetrazolyl group was selected to replace the hetero-aryl moiety of the side chain in telithromycin for designing new compounds. The synthesis of aryltetrazolyl alkylamines was reported in detail. The antibacterial activities of new ketolides were evaluated against a number of pathogens including macrolide-resistant organisms by using telithromycin as the reference. Many of the evaluated compounds exhibited remarkable activities against both erythromycinsusceptible and erythromycin-resistant organisms such as Staphylococcus aureus (except S. aureus AD-08), Pseudomonas aeruginosa and Escherichia coli. Among these, the compound 11e exhibited excellent antibacterial potency against all the strains in comparison with others.

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Section: Antibacterial Activitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, synthesis and antibacterial activity of novel ketolides bearing an aryltetrazolyl-substituted alkyl side chain

et al. 2011

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“…Energy minimization of each structure was performed using Tripos molecular mechanics force field with a distance-dependent (1/r) dielectric function and energy gradient convergence criterion of 0.05 kcal/ (Å mol) [15], which meant molecules were minimized till root-mean-square (rms) deviation 0.05 kcal/ (Å mol) had been achieved. Partial atomic charges were calculated using the Gasteiger-Hückle method [16]. Pyrrolopyrimidine ring was selected as the common structure using compound 36 (the most active compound in dataset) as a template.…”

Section: Data Setsmentioning

confidence: 99%

3D-QSAR and Docking Studies on Pyrrolopyrimidine Derivatives as LIM-Kinase 2 Inhibitors

Sun¹,

Lan²,

Sun³

et al. 2011

LDDD

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The pyrrolopyrimidine derivatives have been regarded as a novel class of LIM-kinase 2 inhibitor. To explore the relationship between the structures of substituted pyrrolopyrimidine derivatives and their inhibitory activities against LIMK2, CoMFA and CoMSIA analyses, and molecular docking studies were performed on a dataset of forty-one compounds. The two 3D-QSAR models resulted from thirty-one molecules in the training set gave r 2 cv values of 0.635 and 0.660, r 2 values of 0.973 and 0.965, respectively. The predictive ability of CoMFA and CoMSIA, determined using a test set of ten compounds, gave predictive correlation coefficients of 0.971 and 0.964, respectively. 3D contour maps generated from CoMFA and CoMSIA along with the docking binding structures provided enough information about the structural requirements for better activity. The results can serve as a useful guideline to design novel LIMK2 inhibitors with better potencies.

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“…Structural energy minimization was performed using the standard Tripos molecular mechanics force field and Gasteiger-Hückel charge 11 . The selected atoms of the template and common in all studied compounds for the superimposition during the alignment were C5, N-7, C-8, C-9 of the benzazepinone scaffold.…”

Section: Molecular Modelling and Alignmentmentioning

confidence: 99%

“…The CoMFA and CoMSIA descriptor fields were obtained by a 3D cubic lattice with grid spacing of 1 Å and extending to 4 Å units beyond the aligned molecules in all directions 11 . The van der Waals potentials and Coulombic terms were calculated by using Tripos force field.…”

Section: Comfa and Comsia Setupmentioning

confidence: 99%

Molecular modelling studies on d-annulated benzazepinones as VEGF-R2 kinase inhibitors using docking and 3D-QSAR

Lan

Sun

Chen

et al. 2010

Journal of Enzyme Inhibition and Medicinal Chemistry

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Exploring 3D-QSAR for Ketolide Derivatives as Antibacterial Agents Using CoMFA and CoMSIA

Cited by 12 publications

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Design, synthesis and antibacterial activity of novel ketolides bearing an aryltetrazolyl-substituted alkyl side chain

Design, synthesis and antibacterial activity of novel ketolides bearing an aryltetrazolyl-substituted alkyl side chain

3D-QSAR and Docking Studies on Pyrrolopyrimidine Derivatives as LIM-Kinase 2 Inhibitors

Molecular modelling studies on d-annulated benzazepinones as VEGF-R2 kinase inhibitors using docking and 3D-QSAR

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