Pharmacophore modeling and 3D QSAR analysis of isothiazolidinedione derivatives as PTP1B inhibitors

Deora, Girdhar Singh, Joshi, Prashant, Rathore, Vandana, Kumar, K. Lalith, Ohlyan, Renu and Kandale, Ajit (2013) Pharmacophore modeling and 3D QSAR analysis of isothiazolidinedione derivatives as PTP1B inhibitors. Medicinal Chemistry Research, 22 7: 3478-3484. doi:10.1007/s00044-012-0349-7


Author Deora, Girdhar Singh
Joshi, Prashant
Rathore, Vandana
Kumar, K. Lalith
Ohlyan, Renu
Kandale, Ajit
Title Pharmacophore modeling and 3D QSAR analysis of isothiazolidinedione derivatives as PTP1B inhibitors
Journal name Medicinal Chemistry Research   Check publisher's open access policy
ISSN 1054-2523
1554-8120
Publication date 2013-07-01
Year available 2012
Sub-type Article (original research)
DOI 10.1007/s00044-012-0349-7
Volume 22
Issue 7
Start page 3478
End page 3484
Total pages 7
Place of publication Cambridge, MA, United States
Publisher Birkhaeuser Boston
Collection year 2014
Language eng
Formatted abstract
The article describes the development of a robust pharmacophore model and investigation of structure activity relationship analysis of 56 isothiazolidinedione derivatives reported as PTP1B inhibitors. A six-point pharmacophore model consisting of four aromatic rings (R), one hydrogen bond donor (D) and one hydrogen bond acceptor (A) with discrete geometries as pharmacophoric features was developed and the generated pharmacophore model was used to derive a predictive 3D QSAR model for the studied dataset. The obtained 3D QSAR model has an excellent correlation coefficient value (r 2 = 0.98) along with good statistical significance as shown by a high Fisher ratio (F = 428.60). The model also exhibits good predictive power confirmed by the high value of cross-validated correlation coefficient (q 2 = 0.62). The QSAR model suggests that hydrophobic aromatic character is crucial for the PTP1B inhibitory activity at the R-15 site.
Keyword Isothiazolidinedione derivatives
PTP1B inhibitors
Pharmacophore modeling
3D Qsar
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ
Additional Notes Published online 24 November 2012

Document type: Journal Article
Sub-type: Article (original research)
Collections: Non HERDC
School of Pharmacy Publications
 
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