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

Lithium trialkylborohydrides were found to mono-dealkylate dialkylphosphonates rapidly (rate of cleavage Me, Bn > 1°). The reaction was applied to the synthesis of a new GABA C antagonist, 2-aminoethyl methylphosphonate ( 4a). Lithium trialkylborohydrides were found to effect rapid monodealkylati...

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Veröffentlicht in:	Bioorganic & Medicinal Chemistry Letters 2007-07, Vol.17 (13), p.3745-3748
Hauptverfasser:	Chowdhury, Sarwat, Muni, Niraj J., Greenwood, Nicholas P., Pepperberg, David R., Standaert, Robert F.
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals BASIC BIOLOGICAL SCIENCES Biological and medical sciences Borohydrides - chemistry CATALYTIC EFFECTS Chemistry, Pharmaceutical - methods DEALKYLATION Dose-Response Relationship, Drug Drug Design Esters - chemistry GABA antagonists GABA C receptors GABAC receptors Gabaergic and benzodiazepinic system gamma-Aminobutyric Acid - analogs & derivatives gamma-Aminobutyric Acid - chemistry Inhibitory Concentration 50 Lithium LITHIUM COMPOUNDS Lithium trialkylborohydrides Magnetic Resonance Spectroscopy Medical sciences Models, Chemical NERVE CELLS Neuropharmacology Neurotransmitter Agents Neurotransmitters. Neurotransmission. Receptors OOCYTES Oocytes - metabolism Organophosphonates - chemical synthesis Organophosphonates - chemistry Pharmacology. Drug treatments Phosphonate esters phosphonate estes PHOSPHONIC ACID ESTERS RECEPTORS SYNTHESIS Xenopus laevis
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