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QSAR study of selective I1-imidazoline receptor ligands

Authorized Users Only
2009
Authors
Nikolić, Katarina
Filipić, Slavica
Agbaba, Danica
Article (Published version)
Metadata
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Abstract
Selective imidazoline1-receptor (I1-R) ligands are used clinically to reduce blood pressure. Thus, there is significant interest in developing new imidazoline analogs with high selectivity and affinity for I1 receptors. A quantitative structure-activity relationship (QSAR) study was carried out on 11 potent I1-R ligands (derivatives of imidazoline, oxazoline and pyrroline) using a multiple linear regression (MLR) procedure. The selected compounds have been studied using B3LYP/3-21G(d, p) and B3LYP/6-31G(d, p) methods. Among the 42 descriptors that were considered in generating the QSAR model, three descriptors (partial atomic charges of nitrogen in the heterocyclic moiety (N-2 charge), log D and the dipole moment of the ligands) resulted in a statistically significant model with r2 0.874 and [image omitted] 0.802. The QSAR models were validated through cross-validation and external test set prediction. The aim of the developed MLR models for the I1-R ligands was to link the structures ...to their reported I1-R binding affinity log(1/Ki). The proposed QSAR models indicate that an increase in log D and the dipole moment value and a decrease in N-2 charge in the heterocyclic moiety are predictors of better selectivity and affinity for I1 receptors. The developed QSAR model is intended to predict the I1-R binding affinity of related compounds and aid in the rational design of new potent and selective I1-R ligands.

Keywords:
I1-receptor / I1-R ligands / centrally acting antihypertensives / QSAR
Source:
Saudi Pharmaceutical Journal, 2009, 20, 1-2, 133-144
Publisher:
  • Taylor & Francis Ltd, Abingdon
Funding / projects:
  • Sinteza, kvantitativni odnosi između strukture/osobina i aktivnosti, fizičko-hemijska karakterizacija i analiza farmakološki aktivnih supstanci (RS-142071)

DOI: 10.1080/10629360902726015

ISSN: 1062-936X

PubMed: 19343588

WoS: 000264827500007

Scopus: 2-s2.0-67650921118
[ Google Scholar ]
12
11
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/1221
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - JOUR
AU  - Nikolić, Katarina
AU  - Filipić, Slavica
AU  - Agbaba, Danica
PY  - 2009
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1221
AB  - Selective imidazoline1-receptor (I1-R) ligands are used clinically to reduce blood pressure. Thus, there is significant interest in developing new imidazoline analogs with high selectivity and affinity for I1 receptors. A quantitative structure-activity relationship (QSAR) study was carried out on 11 potent I1-R ligands (derivatives of imidazoline, oxazoline and pyrroline) using a multiple linear regression (MLR) procedure. The selected compounds have been studied using B3LYP/3-21G(d, p) and B3LYP/6-31G(d, p) methods. Among the 42 descriptors that were considered in generating the QSAR model, three descriptors (partial atomic charges of nitrogen in the heterocyclic moiety (N-2 charge), log D and the dipole moment of the ligands) resulted in a statistically significant model with r2 0.874 and [image omitted] 0.802. The QSAR models were validated through cross-validation and external test set prediction. The aim of the developed MLR models for the I1-R ligands was to link the structures to their reported I1-R binding affinity log(1/Ki). The proposed QSAR models indicate that an increase in log D and the dipole moment value and a decrease in N-2 charge in the heterocyclic moiety are predictors of better selectivity and affinity for I1 receptors. The developed QSAR model is intended to predict the I1-R binding affinity of related compounds and aid in the rational design of new potent and selective I1-R ligands.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Saudi Pharmaceutical Journal
T1  - QSAR study of selective I1-imidazoline receptor ligands
VL  - 20
IS  - 1-2
SP  - 133
EP  - 144
DO  - 10.1080/10629360902726015
ER  - 
@article{
author = "Nikolić, Katarina and Filipić, Slavica and Agbaba, Danica",
year = "2009",
abstract = "Selective imidazoline1-receptor (I1-R) ligands are used clinically to reduce blood pressure. Thus, there is significant interest in developing new imidazoline analogs with high selectivity and affinity for I1 receptors. A quantitative structure-activity relationship (QSAR) study was carried out on 11 potent I1-R ligands (derivatives of imidazoline, oxazoline and pyrroline) using a multiple linear regression (MLR) procedure. The selected compounds have been studied using B3LYP/3-21G(d, p) and B3LYP/6-31G(d, p) methods. Among the 42 descriptors that were considered in generating the QSAR model, three descriptors (partial atomic charges of nitrogen in the heterocyclic moiety (N-2 charge), log D and the dipole moment of the ligands) resulted in a statistically significant model with r2 0.874 and [image omitted] 0.802. The QSAR models were validated through cross-validation and external test set prediction. The aim of the developed MLR models for the I1-R ligands was to link the structures to their reported I1-R binding affinity log(1/Ki). The proposed QSAR models indicate that an increase in log D and the dipole moment value and a decrease in N-2 charge in the heterocyclic moiety are predictors of better selectivity and affinity for I1 receptors. The developed QSAR model is intended to predict the I1-R binding affinity of related compounds and aid in the rational design of new potent and selective I1-R ligands.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Saudi Pharmaceutical Journal",
title = "QSAR study of selective I1-imidazoline receptor ligands",
volume = "20",
number = "1-2",
pages = "133-144",
doi = "10.1080/10629360902726015"
}
Nikolić, K., Filipić, S.,& Agbaba, D.. (2009). QSAR study of selective I1-imidazoline receptor ligands. in Saudi Pharmaceutical Journal
Taylor & Francis Ltd, Abingdon., 20(1-2), 133-144.
https://doi.org/10.1080/10629360902726015
Nikolić K, Filipić S, Agbaba D. QSAR study of selective I1-imidazoline receptor ligands. in Saudi Pharmaceutical Journal. 2009;20(1-2):133-144.
doi:10.1080/10629360902726015 .
Nikolić, Katarina, Filipić, Slavica, Agbaba, Danica, "QSAR study of selective I1-imidazoline receptor ligands" in Saudi Pharmaceutical Journal, 20, no. 1-2 (2009):133-144,
https://doi.org/10.1080/10629360902726015 . .

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