[Studies on the synthesis and bioactivity of alpha-alkylaminobenzyl-phosphonic acids].
OBJECTIVE
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).


CONCLUSIONS
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.
Wang
D X
DX
Institute of Materia Medica, Chinese Academy of Medical Sciences, Beijing 100050, China. wangdx@imm.ac.cn
Dai
C L
CL
Zhao
C
C
Qiu
M C
MC
Tian
G J
GJ
Lin
H
H
D000818:Animals; D001596:Benzylamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D005260:Female; D005269:Femur / Q000166:cytology; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010006:Osteoblasts / Q000166:cytology / Q000187:drug effects*; D051381:Rats
D001596:Benzylamines; D063065:Organophosphonates