Molecular Similarity from Atomic Electrostatic Multipole Comparisons. Application to Anti-HIV Drugs

A procedure is presented for the rapid calculation of the similarity between a pair of molecules based on atomic electrostatic multipole comparison. The multipoles are derived from semiempirical SCF wave functions, and the results obtained compare favorably with ab initio results. The method is illu...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1995-05, Vol.38 (10), p.1635-1640
Main Authors: Burgess, Edward M, Ruell, J. A, Zalkow, Leon H, Haugwitz, Rudiger D
Format: Article
Language:English
Subjects:
AIDS/HIV
Antiviral Agents - chemistry
Antiviral Agents - pharmacology
Biological and medical sciences
Electrochemistry
General pharmacology
HIV-1 - drug effects
HIV-1 - physiology
human immunodeficiency virus
Medical sciences
Pharmacology. Drug treatments
Physicochemical properties. Structure-activity relationships
Structure-Activity Relationship
Virus Replication - drug effects
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Summary:A procedure is presented for the rapid calculation of the similarity between a pair of molecules based on atomic electrostatic multipole comparison. The multipoles are derived from semiempirical SCF wave functions, and the results obtained compare favorably with ab initio results. The method is illustrated by correlating the similarity and anti-HIV-1 activity of a series of azo compounds. Some generalizations are presented on the structure-activity relationships which are based on the atomic multipole distribution in the azo compounds.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00010a007