jm050602z_si_001.pdf (24.18 kB)
Pharmacophoric Features of Biguanide Derivatives: An Electronic and Structural Analysis
journal contribution
posted on 2005-12-01, 00:00 authored by Prasad V. Bharatam, Dhilon S. Patel, Pansy IqbalThe structure and electronic structure of drugs determine their mechanism of action. Correct
structural representation of drugs helps in the proper identification of pharmacophoric features.
Biguanide derivatives are a very important class of drugs, but their electronic structure was
not clearly understood. Ab initio MO and density functional studies revealed the structure of
the most stable tautomer of biguanide. (i) Electron delocalization, (ii) 1,3-H shift, (iii) 1,5-H
shift, (iv) protonation, and (v) deprotonation processes, etc., have been investigated for
biguanide. The molecular electrostatic potential (MESP) surfaces of neutral, protonated, and
deprotonated biguanide have been shown to be similar in their most stable arrangements.
The electrostatic potential of the complementary surface where these systems may bind also
could be identified. Finally, the most stable structure of the important biguanide derivatives
has been given after performing a conformational search.