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Pharmacophore assessment through 3-D QSAR: evaluation of the predictive ability on new derivatives by the application on a series of antitubercular agents.
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Universita ̀ di Roma, P. le A. Moro 5, 00185 Rome, Italy.
Rome Center for Molecular Design Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Universita ̀ di Roma, P. le A. Moro 5, 00185 Rome, Italy.ORCID iD: 0000-0002-4831-3423
Rome Center for Molecular Design Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Universita ̀ di Roma, P. le A. Moro 5, 00185 Rome, Italy.
Rome Center for Molecular Design Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Universita ̀ di Roma, P. le A. Moro 5, 00185 Rome, Italy.
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2013 (English)In: Journal of Chemical Information and Modeling, ISSN 1549-9596, E-ISSN 1549-960X, Vol. 53, no 6, 1463-74 p.Article in journal (Refereed) Published
Abstract [en]

Pharmacophoric mapping is a useful procedure to frame, especially when crystallographic receptor structures are unavailable as in ligand-based studies, the hypothetical site of interaction. In this study, 71 pyrrole derivatives active against M. tuberculosis were used to derive through a recent new 3-D QSAR protocol, 3-D QSAutogrid/R, several predictive 3-D QSAR models on compounds aligned by a previously reported pharmacophoric application. A final multiprobe (MP) 3-D QSAR model was then obtained configuring itself as a tool to derive pharmacophoric quantitative models. To stress the applicability of the described models, an external test set of unrelated and newly synthesized series of R-4-amino-3-isoxazolidinone derivatives found to be active at micromolar level against M. tuberculosis was used, and the predicted bioactivities were in good agreement with the experimental values. The 3-D QSAutogrid/R procedure proved to be able to correlate by a single multi-informative scenario the different activity molecular profiles thus confirming its usefulness in the rational drug design approach.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2013. Vol. 53, no 6, 1463-74 p.
Keyword [en]
Tuberculosis, 3D QSAR, Ligand Based Drug Design, Pyrrole Derivatives, Pharmacophore
National Category
Medicinal Chemistry Biological Sciences Chemical Sciences Computer and Information Science
Identifiers
URN: urn:nbn:se:uu:diva-321304DOI: 10.1021/ci400132qPubMedID: 23617317OAI: oai:DiVA.org:uu-321304DiVA: diva2:1095182
Available from: 2017-05-12 Created: 2017-05-12 Last updated: 2017-05-12

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