Premium
Hydrogen‐bonding effects, electrostatic potential, and the antitumor activity of flavone acetic acid and related compounds. II. Ab initio studies on the second stable conformations
Author(s) -
Fang JianYun,
Thomson Colin
Publication year - 1996
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/(sici)1097-461x(1996)60:4<897::aid-qua12>3.0.co;2-2
Subject(s) - chemistry , hydrogen bond , mulliken population analysis , ab initio , computational chemistry , acetic acid , atomic charge , hydrogen , stereochemistry , molecule , density functional theory , organic chemistry
We previously studied the first stable conformations of flavone acetic acid and related compounds. In this article, a similar investigation was carried out on the second stable conformation of the same compounds. Emphasis is on the conformation dependence of the hydrogen‐bonding effects, the molecular electrostatic potential (MEP), and the antitumor activity shown by these compounds. The results show that the second conformation is about 7.0 kcal mol −1 higher in energy and possibly is an inactive conformation as no correlation has been found between the antitumor activity and the MEP features. In addition, a detailed comparison with the first conformation, which is probably the active conformation, has been made of the geometry, the total energy, the Mulliken charges on some important atoms, hydrogen‐bonding effects, and the MEP minima and isosurfaces. The role of the hydrogen‐bonding effects, which was unclear in our previous work, is clarified in this work. The possible molecular basis of the antitumor activity is suggested. © 1996 John Wiley & Sons, Inc.