[Studies on the synthesis and bioactivity of alpha-alkylaminobenzyl-phosphonic acids].
AIM: To search for some substituted benzyl phosphonic acids as leading compounds with inhibiting effect on osteoclast formation. METHODS: Target compounds were prepared from aromatic aldehydes, primary amine and phosphorous acid using tetramethylenesulfone as solvent via Arbuzov type reaction. The effect on inhibiting the formation of osteoclast-like cells (OLC) of related compounds was studied by incubating the extract of rat femur marrow. RESULTS: Ten compounds of alpha-alkylaminobenzyl phosphonic acids have been synthesized and identified by MS or 1HNMR analysis. Three (2, 8 and 9) of them were found to have notable effect on the inhibition of OLC formation (P < 0.01). CONCLUSION: Among the present substituted benzyl phosphonic acids, the increased aromaticity and hydrophobicity (such as compound 9) can remarkably enhance the ability to inhibit OLC formation.