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Pharmacophoric features of drugs with guanylurea moiety: an electronic structure analysis.
MedLine Citation:
PMID:  23325568     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Several therapeutically important compounds contain guanylurea (GU) moiety. The appropriate tautomeric state of these species has not been explored, preliminary studies indicated that the traditional representation of this class of compounds use a high energy tautomeric state. In this work, quantum chemical studies (HF, B3LYP, MP2, G2MP2 and CBS-Q methods) were performed on the medicinally important GU based drugs so as to identify their stable tautomeric state and to understand the pharmacophoric features of these drugs. Electronic structure studies suggested that GU-1 is the most stable and preferred isomer among the various ketone and enol isomers of the model GU. This study revealed that the general representation adopted in medicinal chemistry literature (GU-5) is about 10 kcal mol(-1) less stable than the energy minimum tautomeric state; and four other alternate structures are possible with energy less than that of the generally represented structure. Hence, it is advisable to consider the energy minimum tautomeric state (GU-1) in all future studies of GU derivatives. Further, the importance of the correct tautomeric representation was demonstrated using a comparative molecular docking analysis of WHR 1049 in α2A adrenergic receptor target.
Authors:
Yoganjaneyulu Kasetti; Prasad V Bharatam
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-1-17
Journal Detail:
Title:  Journal of molecular modeling     Volume:  -     ISSN:  0948-5023     ISO Abbreviation:  J Mol Model     Publication Date:  2013 Jan 
Date Detail:
Created Date:  2013-1-17     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9806569     Medline TA:  J Mol Model     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector-67, S. A. S, Nagar, 160 062, Punjab, India.
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