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Cu(II) complex of an estradiol derivative with potent anti‐inflammatory properties
Author(s) -
Spyriounis Dimitris M.,
Rekka Eleni,
Demopoulos Vassilis J.,
Kourounakis Panos N.
Publication year - 1991
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.2503240902
Subject(s) - chemistry , carrageenan , bromide , ligand (biochemistry) , medicinal chemistry , derivative (finance) , anti inflammatory , formaldehyde , biological activity , chemical synthesis , yield (engineering) , edema , stereochemistry , combinatorial chemistry , nuclear chemistry , in vitro , organic chemistry , pharmacology , receptor , biochemistry , medicine , materials science , financial economics , economics , metallurgy
In the present study, the A‐ring of estradiol was converted to an acetylsalicylic structure which was further complexed with Cu(II). The aim was to combine the anti‐inflammatory properties of estrogens with those of Cu(II) complexes. Key intermediate of the synthesis was 2‐formyl‐estradiol (2) which was prepared in quantitative yield through reaction of the phenoxymagnesium bromide of estradiol with formaldehyde in the presence of HMPA. For a successful reaction, an excess of ethylmagnesium bromide was required, and the mechanism is discussed. The target complex 5 exhibited potent anti‐inflammatory properties, comparable to those of indomethacin, in the carrageenan‐induced rat paw edema. This biological activity was not due either to the steroidal ligand or to the complexed Cu(II) alone.