Stereochemical requirement at 4-position of 4-phenyl-1-arylsulfonylimidazolidinones for their cytotoxicities.
In order to investigate the stereochemical requirements of planar structure at 4-position of 4-phenyl-1-arylsulfonylimidazolidinones (1) for their cytoxicities against human cancer cell lines, the size, the distance from imidazolidinone ring, and the conformation of this moiety were variegated. Replacement of phenyl moiety with naphthyl in compounds 2 and 3 or benzyl moiety in compound 4 sharply reduced activity of 1. Conformational restriction on phenyl ring in compound 5 also resulted in the loss of activity of 1. Therefore, phenyl moiety without any substituents directly attached to imidazolidinone ring of 1 should be considered as an essential pharmacophore for this analog.
Jung
S H
SH
College of Pharmacy, Chungnam National University, Taejon, Korea. jungshh@hanbat.chungnam.ac.kr
Kwak
S J
SJ
Kim
N D
ND
Lee
S U
SU
Lee
C O
CO
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D007093:Imidazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D008968:Molecular Conformation; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D007093:Imidazoles