Molecular similarity analysis on biologically active macrocyclic bis(bibenzyls)

✍ Scribed by György M. Keserű; Mihály Nógrádi

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 412 KB
• Volume: 9
• Category: Article
• ISSN: 0952-3499
• DOI: 10.1002/(sici)1099-1352(199603)9:2<133::aid-jmr254>3.0.co;2-c

✦ Synopsis

Conformational analysis of marchantin A (l), a bis(diary1ether) type, and riccardin A (2), a diarylether-biphenyl type macrocyclic bis(bibenzy1) was carried out by systematic unbounded multiple minimum search (SUMM). Mobility of the macrocyclic rings was analysed by variable temperature '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 Caz+ affinity and activity of 2.