title: Total synthesis of (+)-chaetocin and its analogues: their histone methyltransferase G9a inhibitory activity.
abstract: The first total synthesis of (+)-chaetocin has been accomplished in nine steps starting from known N-Cbz-N-Me-serine using radical alpha-bromination reaction of diketopiperazine 10 and Co(I)-mediated reductive dimerization reaction of 12 as key reactions. The enantiomers show comparable inhibitory activity toward histone methyltransferase (HMT) G9a, but analogues without the sulfur functionality are inactive.
authors.affiliation: RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
authors.forename: Eriko
authors.initials: E
authors.lastname: Iwasa
authors.forename: Yoshitaka
authors.initials: Y
authors.lastname: Hamashima
authors.forename: Shinya
authors.initials: S
authors.lastname: Fujishiro
authors.forename: Eisuke
authors.initials: E
authors.lastname: Higuchi
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ito
authors.forename: Minoru
authors.initials: M
authors.lastname: Yoshida
authors.forename: Mikiko
authors.initials: M
authors.lastname: Sodeoka
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D016503:Drug Delivery Systems; D000076983:Histone Methyltransferases; D011495:Histone-Lysine N-Methyltransferase / Q000037:antagonists & inhibitors*; D006801:Humans; D015394:Molecular Structure; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D010879:Piperazines; C002511:chaetocin; D000076983:Histone Methyltransferases; D011495:Histone-Lysine N-Methyltransferase