ISSN:
0020-7608
Keywords:
Chemistry
;
Theoretical, Physical and Computational Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The requirements for H2-antagonist activity so far identified for most of the known antagonists of histamine are the presence of a heterocyclic ring containing a basic center linked via a methylene chain to a substituted guanidine or thiourea polar side chain. Metiamide is a potent H2 antagonist (pA2=6.06). We have used the ab initio Hartree-Fock (HF) method in order to study the conformational properties of the N3(SINGLE BOND)H tautomers of metiamide molecule and histamine monocation. Three basis set (the 3-21G*, 6-31G**, and 6-31+G**) were used, the results compared, and the geometric parameters fully optimized. Our results indicate the preference of metiamide for a folded conformation with an intramolecular hydrogen bonding between the imidazole ring and one of the NH groups. The optimized geometrical parameters and charge distributions of both molecules, using the Mulliken, and natural bond order (NBO) analysis, are given and discussed. © 1998 John Wiley & Sons, Inc. Int J Quant Chem 69: 117-128, 1998
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
