158221-94-4Relevant academic research and scientific papers
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.
Compared stereoselectivities of the alkylation and aldolization of γ-valerolactone enolates
Anceau, Christophe,Dauphin, Gerard,Coudert, Gerard,Guillaumet, Gerald
, p. 291 - 303 (2007/10/02)
Alkyl condensation of enolates derived from the monosubstituted lactones 1 and 2 is highly stereocontrolled and leads to the 2,4-trans structures.The use of carbonylated compounds as electrophilic agents leads to a complex mixture of the different theoretically possible stereoisomers.The difference between the transition states of alkylation and aldol condensation, as evidenced by conformational analysis of the compounds described here, sheds light on this result.Keywords: γ-valerolactones / alkylation / aldolization / stereoselectivity / conformation
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
