Synthesis and biological activities of phenylahistin derivatives.
X-ray crystallographic analysis was performed and several phenylahistin derivatives were synthesized to elucidate the structural components necessary for the anti-microtubule activity of phenylahistin. We primarily focused on the unique isoprenylated dehydrohistidine structure. Our results showed that a uniplanar pseudo-three-ring structure formed by the hydrogen bonding of diketopiperazine and imidazole rings is important for the anti-microtubule activity of phenylahistin.
Kanoh
K
K
Life Science Research Center, Advanced Technology Research Laboratories, Nippon Steel Corporation, Kawasaki, Japan.
Kohno
S
S
Katada
J
J
Takahashi
J
J
Uno
I
I
Hayashi
Y
Y
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002417:Cattle; D018360:Crystallography, X-Ray; D054659:Diketopiperazines; D006860:Hydrogen Bonding; D007093:Imidazoles / Q000737:chemistry; D051379:Mice; D008870:Microtubules / Q000187:drug effects*; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D054659:Diketopiperazines; D007093:Imidazoles; D010879:Piperazines; C119340:phenylahistin; C029899:imidazole