Polyhydroxylated azepanes as new motifs for DNA minor groove binding agents.
The synthesis of 1,3-bis-[3,4,5,6-tetrahydroxyazepane-N-p-phenoxy] and 1,3-bis-[3,4,5,6-tetrahydroxyazepane-N-p-benzyloxy] propanes is reported. These compounds have been prepared to investigate the potential of incorporating iminosugars as useful recognition elements in DNA minor groove binding agents. The compounds were shown to have very moderate binding affinities for DNA in thermal denaturation and ethidium bromide displacement assays when compared with propamidine. They were also found to possess some in vitro anticancer activity that did not correlate with their DNA binding affinity.
Johnson
Heather A
HA
School of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK.
Thomas
Neil R
NR
D001381:Azepines / Q000737:chemistry / Q000378:metabolism*; D004247:DNA / Q000737:chemistry / Q000187:drug effects* / Q000378:metabolism; D006801:Humans; D006900:Hydroxylation; D009691:Nucleic Acid Denaturation; D014407:Tumor Cells, Cultured
D001381:Azepines; D004247:DNA