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Bioorg Med Chem Lett. July 1, 2007; 17 (13): 3745-8.

Phosphonic acid analogs of GABA through reductive dealkylation of phosphonic diesters with lithium trialkylborohydrides.

Chowdhury S , Muni NJ , Greenwood NP , Pepperberg DR , Standaert RF .

Lithium trialkylborohydrides were found to effect rapid monodealkylation of phosphonic diesters, and this reaction was applied to the synthesis of alkylphosphonic acid 2-aminoethyl esters [H(2)N(CH(2))(2)OP(OH)R, 4], a little-explored class of analogs of the inhibitory neurotransmitter gamma-aminobutyric acid (GABA). Compound 4a (R=Me) proved to be a potent antagonist at human rho1 GABA(C) receptors (expressed in Xenopus laevis oocytes), with an IC(50) of 11.1 microM, but is inactive at alpha(1)beta(2)gamma(2) GABA(A) receptors.

PubMed ID: 17467985
Article link: Bioorg Med Chem Lett.
Grant support: EY001792 NEI NIH HHS , EY013693 NEI NIH HHS , EY016094 NEI NIH HHS , R01 EY016094-01A1 NEI NIH HHS , R03 EY013693-03 NEI NIH HHS , R01 EY016094 NEI NIH HHS , R03 EY013693 NEI NIH HHS

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