title: Total synthesis of schizocommunin and revision of its structure.
abstract: A proposed structure for schizocommunin (Z)-1(hydroxy) and its geometric isomer (E)-1(hydroxy), which exist in a keto form, has been synthesized. However, the spectroscopic data of (Z)-1(keto) and (E)-1(keto) were not consistent with those reported for natural schizocommunin. After reinvestigating the spectral data for natural schizocommunin, we synthesized the quinazolinone derivative (Z)-2 as a revised structure for schizocommunin. All of the spectral data of (Z)-2 were completely identical to those reported for natural schizocommunin. (Z)-2 showed moderate antiproliferative activity.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Chiba University , 1-8-1, Inohana, Chuo-ku, Chiba 260-8675, Japan.
authors.forename: Koji
authors.initials: K
authors.lastname: Uehata
authors.forename: Naoki
authors.initials: N
authors.lastname: Kimura
authors.forename: Kazuya
authors.initials: K
authors.lastname: Hasegawa
authors.forename: Shigeru
authors.initials: S
authors.lastname: Arai
authors.forename: Mayumi
authors.initials: M
authors.lastname: Nishida
authors.forename: Tomoo
authors.initials: T
authors.lastname: Hosoe
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Kawai
authors.forename: Atsushi
authors.initials: A
authors.lastname: Nishida
mesh_terms: D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D007211:Indoles; C405922:schizocommunin