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<span style="font-size:12.0pt;font-family: "Times New Roman";mso-fareast-font-family:"Times New Roman";mso-ansi-language: EN-IN;mso-fareast-language:EN-IN;mso-bidi-language:AR-SA" lang="EN-IN">Modeling, design, chiral aspects and role of <i>para-</i><span style="mso-bidi-font-style:italic">substituents<i> </i>in aryloxypropranolamine based <img src='/image/spc_char/beta.gif' border=0>-<span style="font-size:12.0pt; font-family:"Times New Roman";mso-fareast-font-family:HiddenHorzOCR;mso-ansi-language: EN-IN;mso-fareast-language:EN-IN;mso-bidi-language:AR-SA" lang="EN-IN">blockers <span style="font-size:12.0pt;mso-bidi-font-size:16.0pt;font-family:"Arial Unicode MS"; mso-fareast-font-family:"Arial Unicode MS";mso-bidi-font-family:"Arial Unicode MS"; mso-ansi-language:EN-US;mso-fareast-language:EN-US;mso-bidi-language:AR-SA"></span></span></span></span></span></span>

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Title Modeling, design, chiral aspects and role of para-substituents in aryloxypropranolamine based -blockers
 
Creator Nandel, Fateh S
Dhaliwal, Ramanpreet K
Singh, Balvinder
 
Description 29-35
The conformation of the β -blockers viz. metoprolol, atenolol, bisoprolol, betaxolol
and celiprolol has been investigated using Perturbative Configuration
Interaction of Localized Orbitals (PCILO) method. The conformational energy
maps have been constructed for both the enantiomers (R and S) by rotating the
molecule from the para-substituent
end. The aryloxypropranolamine moiety adopts the same conformation
for all antagonists. The graphical view of R- and S- form of these

antagonists in the lowest energy conformation reveals that it is
only in the S- form of β -blockers, all the three
functionalities- aromatic moiety, amino and β -hydroxyl groups are available for
interaction with β -adrenoceptors. The para-substituents

of the β -blockers adopt a conformation which is
perpendicular to the aryloxy moiety resulting in an L-shaped structure. The β -antagonists possibly partition into the lipid bilayer through the para-substituents and the
aryloxypropranolamine moiety containing the functionalities, thus, lies
parallel to the plane of lipid bilayer for interaction with β -adrenoceptors. Superimposition of S-bisoprolol in lowest energy
conformation with the 3rd putative transmembranous segment of the β -adrenoceptors reveals that the aromatic moiety, amino and β -hydroxyl groups of antagonists are involved in interaction with the
side chains of Trp-109, Asp- 113 and Thr-110 respectively. This has been
further substantiated by the interaction studies on the model system.
 
Date 2012-12-30T20:26:35Z
2012-12-30T20:26:35Z
1999-02
 
Type Article
 
Identifier 0975-0959 (Online); 0301-1208 (Print)
http://hdl.handle.net/123456789/15414
 
Language en_US
 
Rights CC Attribution-Noncommercial-No Derivative Works 2.5 India
 
Publisher NISCAIR-CSIR, India
 
Source IJBB Vol.36(1) [February 1999]