14328-06-4Relevant academic research and scientific papers
Synthesis of chiral 5-aryltetrahydrofuran-2-ones via yeast bioreduction of γ-keto acids and their esters
Mahmoodi,Yousefi-Malekroudi
, p. 365 - 368 (2006)
Enantioselective reduction of γ-keto acids and related γ-keto esters with Saccharomyces cerevisiae (baker's yeast) leads to the formation of the corresponding chiral 5-aryltetrahydrofuran-2-ones in satisfactory chemical and optical yields. Pleiades Publishing, Inc., 2006.
Novel high-affinity and selective biaromatic 4-substituted γ-hydroxybutyric acid (GHB) analogues as GHB ligands: Design, synthesis, and binding studies
H?g, Signe,Wellendorph, Petrine,Nielsen, Birgitte,Frydenvang, Karla,Dahl, Ivar F.,Br?uner-Osborne, Hans,Brehm, Lotte,Fr?lund, Bente,Clausen, Rasmus P.
experimental part, p. 8088 - 8095 (2009/12/07)
γ-Hydroxybutyrate (GHB) is a metabolite of γ-aminobutyric acid (GABA) and has been proposed to function as a neurotransmitter or neuromodulator. GHB is used in the treatment of narcolepsy and is a drug of abuse. GHB binds to both GABAB receptors and specific high-affinity GHB sites in brain, of which the latter have not been linked unequivocally to function, but are speculated to be GHB receptors. In this study, a series of biaromatic 4-substituted GHB analogues, including 4′-phenethylphenyl, 4′-styrylphenyl, and 4′-benzyloxyphenyl GHB analogues, were synthesized and characterized pharmacologically in a [3H](E,RS)-(6,7, 8,9-tetrahydro-5-hydroxy-5H-benzocyclohept-6-ylidene)acetic acid ([ 3H]NCS-382) binding assay and in GABAA and GABA B receptor binding assays. The compounds were selective for the high-affinity GHB binding sites and several displayed Ki values below 100 nM. The affinity of the 4-[4′-(2-iodobenzyloxy)phenyl] GHB analogue 17b was shown to reside predominantly with the R-enantiomer (Ki = 22 nM), which has higher affinity than previously reported GHB ligands.
Direct synthesis of γ-butyrolactones via γ-phenyl substituted butyric acids mediated benzyl radical cyclization
Mahmoodi,Jazayri
, p. 1467 - 1475 (2007/10/03)
Synthesis of several γ-butyrolactones with aromatic substitution at carbon 5 from comparative γ-aryl acids with 25-85% yield are covered. The straight oxidation in the presence of peroxydisulphate-copper(II)chloride system in aqueous medium was applied. The reaction is highly regioselective and leads exclusively to γ-butyrolactone, through stable benzylic radical intermediate.
