title: Molecular similarity analysis on biologically active macrocyclic bis(bibenzyls).
abstract: 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 1H-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 Ca2+ affinity and activity of 2.
authors.affiliation: Department of Chemical Information Technology, Technical University of Budapest, Hungary.
authors.forename: G M
authors.initials: GM
authors.lastname: Keserü
authors.forename: M
authors.initials: M
authors.lastname: Nógrádi
mesh_terms: D001632:Bibenzyls / Q000737:chemistry*; D002396:Catechols / Q000737:chemistry*; D003198:Computer Simulation; D004988:Ethers, Cyclic / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010647:Phenyl Ethers / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D001632:Bibenzyls; D002396:Catechols; D004988:Ethers, Cyclic; D010647:Phenyl Ethers; C103210:riccardin A; C096123:marchantin A