[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.