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Theoretical study of metiamide, a histamine H2 antagonist

✍ Scribed by João B. L. Martins; Carlton A. Taft; Marco A. Perez; Fulvia M. L. G. Stamato; Elson Longo

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
270 KB
Volume
69
Category
Article
ISSN
0020-7608

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✦ Synopsis

The requirements for H -antagonist activity so far identified for most of 2 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 Ž . side chain. Metiamide is a potent H antagonist pA2 s 6.06 . We have used the ab initio 2 Ž . Hartree᎐Fock HF method in order to study the conformational properties of the N -H 3 Ž U tautomers of metiamide molecule and histamine monocation. Three basis set the 3-21G , UU UU .

6-31G , and 6-31qG

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 Ž . both molecules, using the Mulliken, and natural bond order NBO analysis, are given and discussed.

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