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

…, NP Greenwood, DR Pepperberg, RF Standaert

Index: Chowdhury, Sarwat; Muni, Niraj J.; Greenwood, Nicholas P.; Pepperberg, David R.; Standaert, Robert F. Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 13 p. 3745 - 3748

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Citation Number: 8

Abstract

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 [H2N (CH2) 2OP (OH) R, 4], a little-explored class of analogs of the inhibitory neurotransmitter γ-aminobutyric acid (GABA). Compound 4a (R= Me) proved to be a potent antagonist at human ρ1 GABAC receptors (expressed in Xenopus laevis oocytes), with an ...