Quantitative structure-activity relationships for 1,4-dihydropyridine calcium channel antagonists (nifedipine analogues): A quantum chemical/classical approach

A quantum chemical (AM1) combined with a classical study of structure‐activity relationships for 1,4‐dihydropyridines (nifedipine analogues) was performed. The biological data were taken from the literature. The quantum chemical parameters tested were energies of HOMO and LUMO, dipole moment (total...

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Bibliographic Details
Published in:Journal of pharmaceutical sciences 1994-08, Vol.83 (8), p.1110-1115
Main Authors: Gaudio, Anderson Coser, Korolkovas, Andrejus, Takahata, Yuji
Format: Article
Language:English
Subjects:
Biological and medical sciences
Calcium Channel Blockers - chemistry
Calcium Channel Blockers - pharmacology
Cardiovascular system
Chemical Phenomena
Chemistry, Physical
Medical sciences
Miscellaneous
Molecular Conformation
Nifedipine - analogs & derivatives
Nifedipine - chemistry
Nifedipine - pharmacology
Pharmacology. Drug treatments
Quantum Theory
Regression Analysis
Structure-Activity Relationship
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Summary:A quantum chemical (AM1) combined with a classical study of structure‐activity relationships for 1,4‐dihydropyridines (nifedipine analogues) was performed. The biological data were taken from the literature. The quantum chemical parameters tested were energies of HOMO and LUMO, dipole moment (total and partial), hardness, Mulliken electronegativity, frontier orbital indices, and others. Also tested were classical parameters like Hansch hydrophobic constant, π; Hammett electronic constant for the meta position, σm; and the Verloop sterimol parameters, B1 and L. The van der Waals volume was also tested. The pharmacological activities of the para monoderivatives are negatively correlated with the molecular volume, i.e. a steric factor. The meta position of the phenyl ring is affected by steric and electronic parameters, whereas the ortho position seems to be affected by hydrophobic and electronic parameters.
ISSN:0022-3549
1520-6017
DOI:10.1002/jps.2600830809