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Hydrogen‐bonding effects, electrostatic potential, and the antitumor activity of flavone acetic acid and related compounds. I. Ab initio studies on the first stable conformations
Author(s) -
Fang JianYun,
Thomson Colin
Publication year - 1995
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560540507
Subject(s) - ab initio , chemistry , hydrogen bond , basis set , computational chemistry , acetic acid , hydrogen , ab initio quantum chemistry methods , molecule , stereochemistry , density functional theory , organic chemistry
Ab initio investigations have been carried out to account for the antitumor activity of flavone acetic acid (FAA) and related compounds. The hydrogen‐bonding conformation was chosen for all the compounds and obtained through a restricted geometry optimization with the 3‐21 G basis set. Three key regions in the molecular electrostatic potential isosurfaces [ V ( r ) ∼ −0.015 au] are found to be involved in the activity. Region 1 is the most important. Its existence implies the activity and its size determines the strength of the activity. Region 2 is another factor which can change the strength of the activity. Region 3 corresponds to the hydrogen‐bonding effects which have been analyzed in detail, but its role is still not clear. Finally, basis‐set effects on the molecular electrostatic potential have been briefly discussed. © 1995 John Wiley & Sons, Inc.