134755-18-3Relevant academic research and scientific papers
The synthetic and biological studies of discorhabdins and related compounds
Wada, Yasufumi,Harayama, Yu,Kamimura, Daigo,Yoshida, Masako,Shibata, Tomoyuki,Fujiwara, Kousaku,Morimoto, Koji,Fujioka, Hiromichi,Kita, Yasuyuki
supporting information; experimental part, p. 4959 - 4976 (2011/08/06)
Various analogues of the marine alkaloids, discorhabdins, have been synthesized. The strategy contains spirocyclization with phenyliodine(iii) bis(trifluoroacetate) (PIFA), oxidative fragmentation of the β-amino alcohols with the hypervalent iodine reagent C6F 5I(OCOCF3)2, the detosylation and dehydrogenation reaction of the pyrroloiminoquinone unit in the presence of a catalytic amount of NaN3 and the bridged ether synthesis with HBr-AcOH as the key reactions. All the synthesized compounds were evaluated by in vitro MTT assay for cytotoxic activity against the human colon cancer cell line HCT-116. Furthermore, the discorhabdin A oxa analogues were also evaluated against four kinds of tumor model cells, a human colon cancer cell line (WiDr), a human prostate cancer cell line (DU-145) and murine leukemia cell lines (P388 and L1210). For the identification of the target, discorhabdin A and the discorhabdin A oxa analogue were evaluated by an HCC panel assay. In the test, discorhabdins could have a novel mode of action with the tumor cells. The Royal Society of Chemistry 2011.
Total synthesis of discorhabdin C: A general aza spiro dienone formation from O-silylated phenol derivatives using a hypervalent iodine reagent
Kita, Yasuyuki,Tohma, Hirofumi,Inagaki, Masanao,Hatanaka, Kenji,Yakura, Takayuki
, p. 2175 - 2180 (2007/10/02)
Hypervalent iodine oxidation of O-silylated phenols bearing various types of aminoquinones at the para position in 2,2,2-trifluoroethanol gave azacarbocyclic spiro dienones in good yields. Using this method, the first total synthesis of discorhabdin C, wh
Hypervalent iodine oxidation of O-silylated phenol derivatives to azacarbocyclic spirodienones; synthetic approach to the anticancer marine alkaloid, discorhabdin C
Kita,Tohma,Inagaki,Hatanaka,Kikuchi,Yakura
, p. 2035 - 2038 (2007/10/02)
Hypervalent iodine oxidation of O-silylated phenols bearing various types of aminoquinones at the p-position in 2,2,2-trifluoroethanol gave azacarbocyclic spirodienones in good yields and application of this reaction to the synthetic approach to discorhab
