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Molecular similarity analysis on biologically active macrocyclic bis(bibenzyls)
Author(s) -
Keserű György M.,
Nógrádi Mihály
Publication year - 1996
Publication title -
journal of molecular recognition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.401
H-Index - 79
eISSN - 1099-1352
pISSN - 0952-3499
DOI - 10.1002/(sici)1099-1352(199603)9:2<133::aid-jmr254>3.0.co;2-c
Subject(s) - steric effects , conformational isomerism , chemistry , stereochemistry , bibenzyl , biphenyl , calmodulin , computational chemistry , molecule , organic chemistry , calcium
Conformational analysis of marchantin A (1), a bis(diarylether) type, and riccardin A (2), a diarylether‐biphenyl type macrocyclic bis(bibenzyl) was carried out by systematic unbounded multiple minimum search (SUMM). Mobility of the macrocyclic rings was analysed by variable temperature 1 H‐NMR study. Molecular similarity analysis was performed on the minimum energy conformers of 1 and 2 comparing their steric, electrostatic and hydrophobic properties. Correlation between complexation properties and calmodulin inhibitor activity was established. Differences in steric and electrostatic profiles may be responsible for the reduced Ca 2+ affinity and activity of 2.