150-96-9Relevant articles and documents
Synthesis and antitumour activity of β-hydroxyisovalerylshikonin analogues
Rao, Zhen,Liu, Xin,Zhou, Wen,Yi, Jing,Li, Shao-Shun
experimental part, p. 3934 - 3941 (2011/11/12)
A series of novel β-hydroxyisovalerylshikonin analogues bearing oxygen-containing substituents at the side-chain hydroxyl of shikonin were designed and synthesized. The cytotoxicities of these compounds were evaluated in vitro against multi-drug resistant (MDR) cell lines DU-145 and HeLa. Most compounds exhibited significant inhibitory activity on both cell lines. The structure-activity relationship showed the analogues with ether substituents displayed the most potent antitumour activity and selective cytotoxicity towards DU-145. Among the compounds with ether substituents, increasing the steric hindrance in the carbon bearing β-hydroxyl or replace the β-hydroxyl with acetoxy or methoxy would lead to the decline of cytotoxicity.
Synthesis of perhydrooxazinones from 2-aza-3-trimethylsilyloxy-1,3- butadiene. A general route to 3,3-disubstituted-β-hydroxy acids
Bandini, Elisa,Martelli, Giorgio,Spunta, Giuseppe,Bongini, Alessandro,Panunzio, Mauro
, p. 1735 - 1738 (2007/10/03)
1-Phenyl-2-aza-3-trimethylsilyloxy-1,3-butadiene reacts with aliphatic, aromatic and cyclic ketones to give in good to excellent yields 6,6- disubstituted-1,3-perhydro-oxazin-4-ones which, in turn, have been readily converted into β-hydroxy carboxylic acids.
Enantioselective Hydrolysis of 3-Hydroxy-3-methylalkanoic Acid Esters with Pig Liver Esterase
Wilson, William K.,Baca, Shawn B.,Barber, Yolanda J.,Scallen, Terence J.,Morrow, Cary J.
, p. 3960 - 3966 (2007/10/02)
Pig liver esterase has been shown to stereoselectively hydrolyze the R enantiomer of several chiral 3-hydroxy-3-methylalkanoic acid esters of the form RC(Me)(OH)CH2COOR', where R = Et, CH2=CHCH2, Me(CH2)5, (MeO)2CHCH2, and PhCH2OCH2CH2 and R'= Me or Et.The unhydrolyzed ester and the reesterified carboxylic acid were analyzed for enantiomeric purity by NMR using the chiral shift reagent Eu(hfc)3.For the compounds studied, the S enantiomers consistently showed greater induced shifts.Products of the resolution are potential intermediates in the preparation of compactin analogues having defined stereochemistry at carbon-3.These analogues will be useful in testing the hypothesis that the hypocholesterolemic activity of compactin and its analogues resides in their ability to mimic the binding of mevaldic acid coenzyme A hemithioacetal to HMG-CoA reductase but not be reduced to mevalonate.