31004-76-9Relevant academic research and scientific papers
Synthesis and structure-activity studies of alkyl-substituted γ-butyrolactones and γ-thiobutyrolactones: Ligands for the picrotoxin receptor
Canney,Holland,Levine,McKeon,Ferrendelli,Covey
, p. 1460 - 1467 (2007/10/02)
A series of γ-butyrolactones and γ-thiobutyrolactones possessing a variety of alkyl groups and alkyl-substitution patterns was prepared and evaluated for anticonvulsant and convulsant activity. Behavioral studies performed on these compounds suggest that maximal anticonvulsant activity (against maximal electroshock and pentylenetetrazol) results when three or four carbon atoms are present at the α-position. For convulsant potency, a similar dependence on the size of the alkyl chain at the β-position was observed. Additional γ-dimethyl groups were found to increase the convulsant potency of a β-substituted compound and to cause an an α-substituted anticonvulsant to become a convulsant. In general, sulfur for oxygen heteroatom substitution in the α-substituted lactones resulted in improved anticonvulsant potency and spectrum of activity. Binding of these compounds to the picrotoxin site of the GABA receptor complex was demonstrated with a [35S]-tert-butylbicyclophosphorothionate radioligand binding assay. Measurements of brain concentrations for selected compounds supports a hypothesis that correlates binding to the picrotoxin site with the pharmacological effects of these compounds.
Facile Synthesis of α,β, and/or γ-Alkylsubstituted γ-Butyrolactones Using Readily Prepared Olefinic Esters
Canney, Daniel J.,Levine, Jeffrey A.,Lu, Hwang-Fun,Covey, Douglas F.
, p. 2065 - 2073 (2007/10/02)
Starting with easily prepared olefinic esters, efficient and versatile routes for the synthesis of γ-butyrolactones possessing a variety of alkyl-groups and alkyl-substitution patterns are reported.
Regioselectivity in Nickel(II)-Mediated Oxidations of Diols
Doyle, Michael P.,Dow, Robert L.,Bagheri, Vahid,Patrie, William, J.
, p. 476 - 480 (2007/10/02)
Oxidations of 2- and 4-substituted 1,4-butanediols to their corresponding γ-butyrolactones by the combination of molecular bromine and nickel(II) alkanoate occur with a high degree of regioselectivity.The influence of the alkanoate ligand, of substituents at the 2-position of 1,4-butanediols, and of solvent on oxidation regiocontrol is examined, and comparison of regioselectivity in diol oxidations is made with representative conventional oxidative methods.Regiocontrol in nickel(II)-mediated reactions is proposed to be derived from steric constraints for oxidativehydrogen transfer to the alkanoate ligand of nickel(II) in the diol-associated complex.Alternate use of cobalt(II) alkanoates provides regiocontrol in diol oxidations that is comparable or superior to that obtained with nickel(II) alkanoates in bromine oxidations.
Reversal of Regioselectivity in the Reduction of gem-Disubstituted Cyclic Carboxylic Acid Anhydrides
Morand, Peter,Salvator, Judith,Kayser, Margaret M.
, p. 458 - 459 (2007/10/02)
The regioselective partial reduction of gem-disubstituted cyclic carboxylic acid anhydrides to the corresponding γ-lactones with LiAlH4 or NaBH4 is almost completely reversed when potassium tri-s-butylborohydride is used as the reducing agent.
STERIC SELECTIVITY IN OXIDATION OF DIOLS
Doyle, Michael P.,Dow, Robert L.,Bagheri, Vahid,Patrie, William J.
, p. 2795 - 2798 (2007/10/02)
Oxidations of 2,2-disubstituted-1,4-butenediols by the combination of nickel(II) bromide and benzoyl peroxide and by trityl tetrafluoroborate produce β,β-disubstituted-γ-butyrolactones with exceptional selectivity.
