QSAR studies on benzene sulfonamide carbonic anhydrase inhibitors: need of hydrophobic parameter for topological modeling of binding constants of sulfonamides to human CA-II

Khadikar, Padmakar V.; Sharma, Vimukta; Karmarkar, Sneha; Supuran, Claudiu T.

doi:10.1016/j.bmcl.2004.12.056

Cited by 28 publications

(15 citation statements)

References 23 publications

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“…It shows that the correlation between Sz index and the analgesic activity (logIC 50 ) depends on the type of the compounds to which the analgesic belongs. CA-II Activity = 0.0034 Sz -0.0843 P xx + 0.2518 P zz + 4.2219 logP + 45.5773 (115) One of the authors (PVK) thanks to Prof. Ivan Gutman for his personal interest and to all those colleagues who worked with him on Szeged index and remained as coauthors in various publications. n = 35, Se = 8.0556, r = 0.6633, F = 5.107…”

Section: Xafs Parameters [158]mentioning

confidence: 99%

“…Many physicochemical properties related to organic compounds acting as drugs were modeled by using Szeged index to develop structure-property-relationships [15,17,55,57,73,80,85,89,91,95,102,104,105,112,[115][116][117][118][119]. Important physicochemical properties, which were modeled using Szeged index being: molecular weight (MW) [68], density (d) [68], boiling point (bp) [68], vapor pressure (VP) [35], molar volume (MV) [68] , molar refraction (MR) [35], parachor (PR) [68], van der Waals volume (Vw) [68], equalized electro negativity (χ eq ) [68], dipole moments (µ) [68], proton-ligand formation constants [75,141]and polarizability (α) [68].…”

Section: Applications Of Szeged Index For Modeling Physicochemical Prmentioning

confidence: 99%

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Szeged Index - Applications for Drug Modeling&#

Khadikar¹,

Karmarkar²,

Agrawal

et al. 2005

LDDD

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In this review we describe various applications of Szeged (Sz) index for modeling physicochemical properties as well as physiological activities of organic compounds acting as drugs or possess pharmacological activity.Keywords: Szeged index, physicochemical properties, biological activity, drug design, QSPR, QSAR, QSTR, multiple regression analysis. # On the eve of 70 th birthday of both Prof. Padmakar V. Khadikar and his wife Mrs. Kusum Khadikar.

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Section: Xafs Parameters [158]mentioning

confidence: 99%

Section: Applications Of Szeged Index For Modeling Physicochemical Prmentioning

confidence: 99%

Szeged Index - Applications for Drug Modeling&#

Khadikar¹,

Karmarkar²,

Agrawal

et al. 2005

LDDD

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“…potency [3][4][5][6][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25]. Another objective of the present study is to investigate the role of hydrophobic term for obtaining excellent QSAR model.…”

Section: Introductionmentioning

confidence: 99%

Development of Quantitative Structure-Activity Relationship for a Set of Carbonic Anhydrase Inhibitors: Use of Quantum and Chemical Descriptors

Khadikar¹,

Deeb²,

Jaber³

et al. 2006

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A set of 24 descriptors consisting of quantum and chemical descriptors have been used to model binding constant (logK) of the benzene sulfonamides to human CAII. Simple as well as multiple regression have indicated that MNC (most negative charge) is the most dominating parameter to be used in modeling log K. Excellent results are obtained in multi-parametric regression. The results are critically discussed using a variety of statistics, which indicated that the hydrophobic term (log P) is not essential to yield excellent models.

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“…Many CA isozymes are druggable targets, and their inhibitors may have applications in the design of antiglaucoma, antitumor, anticonvulant or antiobesity agents among others [13][14][15][16][17][18][19][20][21][22]. At this stage it is worh mentioning that the sulfonamides substituted at the sulfamoyl moiety (ArSO 2 NHR) are known for about 70 years as antibacterial agents.…”

Section: Introductionmentioning

confidence: 99%

QSAR studies for the inhibition of the transmembrane carbonic anhydrase isozyme XIV with sulfonamides using PRECLAV software

Singh

Khadikar²,

Scozzafava

et al. 2009

Journal of Enzyme Inhibition and Medicinal Chemistry

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QSAR studies for the inhibition of isozyme XIV of human carbonic anhydrase (CA, EC 4.2.1.1) by a series of sulfonamides including clinically used derivatives (acetazolamide, methazolamide, ethoxzolamide, dichlorophenamide, dorzolamide, brinzolamide, benzolamide, and zonisamide) are presented. Statistical calculations done using the PRECLAV program, for the correlation between the observed inhibition values and the calculated ones were good (s ¼ 0.2416, r 2 ¼ 0.9259, F ¼ 75.0196, r 2 CV ¼ 0:8985). The obtained results by using PRECLAV descriptors have been compared with those where the descriptors have been calculated with HYPERCHEM. The obtained QSAR equations pointed out the fact that the CA inhibitory activity decreased for unsubstituted (at the organic scaffold) aromatic/heteroaromatic sulfonamides, but was favored by the presence of alkyl groups substituting the scaffold, which led to a higher internal topological diversity, as well as by the presence of condensed aromatic rings in the structure of these enzyme inhibitors.

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QSAR studies on benzene sulfonamide carbonic anhydrase inhibitors: need of hydrophobic parameter for topological modeling of binding constants of sulfonamides to human CA-II

Cited by 28 publications

References 23 publications

Szeged Index - Applications for Drug Modeling&#

Szeged Index - Applications for Drug Modeling&#

Development of Quantitative Structure-Activity Relationship for a Set of Carbonic Anhydrase Inhibitors: Use of Quantum and Chemical Descriptors

QSAR studies for the inhibition of the transmembrane carbonic anhydrase isozyme XIV with sulfonamides using PRECLAV software

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