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Journal of Enzyme Inhibition and Medicinal Chemistry Volume 32, 2017 - Issue 1

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Original Article

3D QSAR studies, pharmacophore modeling, and virtual screening of diarylpyrazole–benzenesulfonamide derivatives as a template to obtain new inhibitors, using human carbonic anhydrase II as a model protein

Yeganeh Entezari HeraviDepartment of Chemistry, Faculty of Science, University of Tehran, Tehran, Iran;

Hassan SereshtiDepartment of Chemistry, Faculty of Science, University of Tehran, Tehran, Iran; Correspondence[email protected] [email protected]

Ali Akbar SabouryInstitute of Biochemistry and Biophysics, University of Tehran, Tehran, Iran; Correspondence[email protected] [email protected]

Jahan GhasemiDepartment of Chemistry, Faculty of Science, University of Tehran, Tehran, Iran;

Marzieh AmirmostofianDepartment of Medicinal Chemistry, School of Pharmacy, Zabol University of Medical Sciences, Zabol, Iran;

Claudiu T. SupuranDipartimento Neurofarba, Universita degli Studi di Firenze, Sezione di Scienze Farmaceutiche, Florence, Sesto Fiorentino, Italy

Pages 688-700 | Received 06 Aug 2016, Accepted 22 Sep 2016, Published online: 19 Mar 2017

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https://doi.org/10.1080/14756366.2016.1241781
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Table 1. (a) Structures and experimental inhibitory potency (K_i, nM) for compounds of the general structures Ι and II.

Display Table

Table 1. (b) Structures and experimental inhibitory potency (K_i, nM) for compounds of the general structures III, IV, and V.

Display Table

Table 1. (c) Structures and experimental inhibitory potency (K_i, nM) for compounds of the general structures VI, VII, and VIII.

Display Table

Table 2. Summary of the results obtained from the CoMFA, CoMFA-RF, and CoMSIA models.

Download CSV Display Table

Table 3. Experimental and predicted inhibitory activities (pK_i) with residual values for the training and test set compounds.

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Figure 1. CoMFA contour maps based on compound 26: (a) steric, (b) electrostatic, and (c) consolidated steric and electrostatic.

Table 4. Structural form of the more active compounds than acetazolamide (AZA).

Display Table

Figure 2. CoMSIA contour maps for hydrophobic and hydrophilic features: (a) for compound 26 and (b) for more active compounds than AZA.

Figure 3. CoMSIA contour maps for the absence and the presence of hydrogen bond donor features based on (a) compound 26 and (b) more active compound than AZA.

Figure 4. CoMSIA contour maps for the absence and the presence of hydrogen bond acceptor features based on (a) compound 26 and (b) more active compound than AZA.

Table 5. Structures and GOLD fitness score values for the hit compounds.

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Table 6. Prediction of ADME properties of hits using Qikprop.

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Table 7. Prediction of drug likeness parameters and assessment of risk factors by OSIRIS Property Explorer.

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Supplemental material

IENZ_1241781_Supplementary_Material.pdf

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3D QSAR studies, pharmacophore modeling, and virtual screening of diarylpyrazole–benzenesulfonamide derivatives as a template to obtain new inhibitors, using human carbonic anhydrase II as a model protein

Table 1. (a) Structures and experimental inhibitory potency (K_i, nM) for compounds of the general structures Ι and II.

Table 1. (b) Structures and experimental inhibitory potency (K_i, nM) for compounds of the general structures III, IV, and V.

Table 1. (c) Structures and experimental inhibitory potency (K_i, nM) for compounds of the general structures VI, VII, and VIII.

Table 2. Summary of the results obtained from the CoMFA, CoMFA-RF, and CoMSIA models.

Table 3. Experimental and predicted inhibitory activities (pK_i) with residual values for the training and test set compounds.

Table 4. Structural form of the more active compounds than acetazolamide (AZA).

Table 5. Structures and GOLD fitness score values for the hit compounds.

Table 6. Prediction of ADME properties of hits using Qikprop.

Table 7. Prediction of drug likeness parameters and assessment of risk factors by OSIRIS Property Explorer.

IENZ_1241781_Supplementary_Material.pdf

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3D QSAR studies, pharmacophore modeling, and virtual screening of diarylpyrazole–benzenesulfonamide derivatives as a template to obtain new inhibitors, using human carbonic anhydrase II as a model protein

Figures & data

Table 1. (a) Structures and experimental inhibitory potency (Ki, nM) for compounds of the general structures Ι and II.

Table 1. (b) Structures and experimental inhibitory potency (Ki, nM) for compounds of the general structures III, IV, and V.

Table 1. (c) Structures and experimental inhibitory potency (Ki, nM) for compounds of the general structures VI, VII, and VIII.

Table 2. Summary of the results obtained from the CoMFA, CoMFA-RF, and CoMSIA models.

Table 3. Experimental and predicted inhibitory activities (pKi) with residual values for the training and test set compounds.

Table 4. Structural form of the more active compounds than acetazolamide (AZA).

Table 5. Structures and GOLD fitness score values for the hit compounds.

Table 6. Prediction of ADME properties of hits using Qikprop.

Table 7. Prediction of drug likeness parameters and assessment of risk factors by OSIRIS Property Explorer.

IENZ_1241781_Supplementary_Material.pdf

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To cite this article:

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Table 1. (a) Structures and experimental inhibitory potency (K_i, nM) for compounds of the general structures Ι and II.

Table 1. (b) Structures and experimental inhibitory potency (K_i, nM) for compounds of the general structures III, IV, and V.

Table 1. (c) Structures and experimental inhibitory potency (K_i, nM) for compounds of the general structures VI, VII, and VIII.

Table 3. Experimental and predicted inhibitory activities (pK_i) with residual values for the training and test set compounds.