6533b854fe1ef96bd12ae768

RESEARCH PRODUCT

Theoretical study of selective H3 receptor antagonists of histamine

Mario R. EstradaE.a. JaureguiF. Tomas-vertCarlos A. PonceRicardo D. Enriz

subject

education.field_of_studyThioperamideStereochemistryChemistryPopulationAntagonistMNDOCondensed Matter PhysicsBiochemistrychemistry.chemical_compoundComputational chemistrymedicineImidazoleBetahistinePhysical and Theoretical ChemistryHistamine H3 receptoreducationHistaminemedicine.drug

description

Abstract The conformations and charge distributions of three selective H3 receptor antagonists of histamine were determined using the MNDO approach. The results suggest that the conformational flexibilities of betahistine, N α-(2-phenylacetyl)histamine and thioperamide are different; however, the low-energy conformations of these compounds show closely related spatial orderings. The MNDO calculations predict a significant population of the N1H form in the imidazole systems of N α-(2-phenylacetyl)histamine and thioperamide. Our results indicate that the conformational behaviour of H3 antagonists is closely similar to that reported for H2 antagonists of histamine. These results emphasize the importance of tautomeric and electronic effects rather than conformational factors in accounting for the different antagonist activity at H2 or H3 receptors of several H2 ligands.

yearjournalcountryeditionlanguage
1993-03-01Journal of Molecular Structure: THEOCHEM
https://doi.org/10.1016/0166-1280(93)87088-u