4730-77-2Relevant academic research and scientific papers
Inhibition of purple acid phosphatase with α-alkoxynaphthylmethylphosphonic acids
McGeary, Ross P.,Vella, Peter,Mak, Jeffrey Y.W.,Guddat, Luke W.,Schenk, Gerhard
supporting information; experimental part, p. 163 - 166 (2009/04/10)
Purple acid phosphatases (PAPs) are binuclear hydrolases that catalyse the hydrolysis of a range of phosphorylated substrates. Human PAP is a major histochemical marker for the diagnosis of osteoporosis. In patients suffering from this disorder, PAP activity contributes to increased bone resorption and, therefore, human PAP is a key target for the development of anti-osteoporotic drugs. This manuscript describes the design and synthesis of derivatives of 1-naphthylmethylphosphonic acids as inhibitors of PAP. The Ki values of these compounds are as low as 4 μM, the lowest reported to date for a PAP inhibitor.
Green, palladium-catalyzed synthesis of benzylic H-phosphinates from hypophosphorous acid and benzylic alcohols
Coudray, Laetitia,Montchamp, Jean-Luc
supporting information; experimental part, p. 4101 - 4103 (2009/05/07)
Benzylic alcohols cross-couple directly with concentrated H 3PO2 by using Pd/xantphos (1 or 2 mol-%). Depending on the substrate, DMF at 110 °C or t-AmOH at reflux with a Dean-Stark trap can be used. A broad range of benzylic alcohols react successfully to give moderate to good yields of the products. The preparation of other organophosphorus compounds (phosphinic and phosphonic acids) is also demonstrated. Asymmetric reaction with (R)-1-(2-naphthyl)-ethanol provids the corresponding H-phosphinic acid in 77% ee. The methodology provides a green, PCl3-free route to benzylic-H-phosphinic acids. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
