158221-94-4Relevant articles and documents
Syntheses of cytotoxic novel arctigenin derivatives bearing halogen and alkyl groups on aromatic rings
Yamauchi, Satoshi,Wukirsari, Tuti,Ochi, Yoshiaki,Nishiwaki, Hisashi,Nishi, Kosuke,Sugahara, Takuya,Akiyama, Koichi,Kishida, Taro
, p. 4199 - 4203 (2017)
The new lignano-9,9′-lactones (α,β-dibenzyl-γ-butyrolactone lignans), which showed the higher cytotoxicity than arctigenin, were synthesized. The well-known cytotoxic arctigenin showed activity against HL-60 cells (EC50 = 12 μM), however, it was inactive against HeLa cells (EC50 > 100 μM). The synthesized (3,4-dichloro, 2′-butoxy)-derivative 55 and (3,4-dichloro, 4′-butyl)-derivative 66 bearing the lignano-9,9′-lactone structures showed the EC50 values of 10 μM and 9.4 μM against HL-60 cells, respectively. Against HeLa cells, the EC50 value of the derivative 66 was 27 μM. By comparing the activities with the corresponding 9,9′-epoxy structure (tetrahydrofuran compounds), the importance of the lactone structure of 55 and 66 for the higher activities was shown. The substituents on the aromatic ring of the lignano-9,9′-lactones affected the cytotoxicity level, observing more than 10-fold difference.
HIGHLY STEREOSELECTIVE CONSTRUCTION OF CHIRAL QUATERNARY CARBON: ASYMMETRIC SYNTHESIS OF β,β-DISUBSTITUTED γ-BUTYROLACTONES
Tomioka, Kiyoshi,Cho, Youn-Sang,Sato, Fuminori,Koga, Kenji
, p. 1621 - 1624 (2007/10/02)
Asymmetric synthesis of β,β-disubstituted γ-butyrolactones was carried out in highly stereoselective and predictable way, by means of sequential dialkylation of (S)-γ-trityloxymethyl-γ-butyrolactone followed by lactone carbonyl transposition.Application t
