title: Ferrocenyl chalcones versus organic chalcones: a comparative study of their nematocidal activity.
abstract: A series of 30 organic chlacones and 33 ferrocenyl (Fc) chalcones were synthesized and characterized by melting point, elemental analysis, spectroscopy ((1)H NMR and FTIR) and, in two cases, by X-ray crystallography. The biological activity of each compound (10(-4)M in DMSO) against the model nematode Caenorhabditis elegans was examined in terms of % mortality (percent nematodes that died) and % fecundity (percent nematodes that reproduced) and compared to that obtained for the control medium (1% DMSO) over a 14-day period. Detailed conformational analyses for two Fc-chalcones (studied also by X-ray crystallography) were performed via molecular modeling studies. In general, the organic chalcones were found to be less polar than their Fc analogs. Some structure-activity relationships (SARs) were determined: (a) The nematocidal activities of the organic chalcones in this series were found to be much greater than those of their ferrocenyl analogs. (b) The position of the carbonyl group played a central role in the biological activity of both classes of chalcones studied. (c) For both classes of chalcones, lipophilicity of a compound seemed to play a significant role in its nematocidal activity. (d) The planarity of a ferrocenyl-chlacone seems to play a role in its activity.
authors.affiliation: Department of Chemistry (M/S SB-70), California State University, Fresno, CA 93740, USA. sattar@csufresno.edu
authors.forename: Saeed
authors.initials: S
authors.lastname: Attar
authors.forename: Zachary
authors.initials: Z
authors.lastname: O'Brien
authors.forename: Hasan
authors.initials: H
authors.lastname: Alhaddad
authors.forename: Melissa L
authors.initials: ML
authors.lastname: Golden
authors.forename: Alejandro
authors.initials: A
authors.lastname: Calderón-Urrea
mesh_terms: D000818:Animals; D000969:Antinematodal Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D017173:Caenorhabditis elegans / Q000187:drug effects; D047188:Chalcones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D005296:Ferrous Compounds / Q000737:chemistry*; D000075163:Metallocenes; D008968:Molecular Conformation; D013329:Structure-Activity Relationship
chemical_list: D000969:Antinematodal Agents; D047188:Chalcones; D005296:Ferrous Compounds; D000075163:Metallocenes; C004998:ferrocene