FREE T O ANALYTICAL CHEMISTS
Addition of at methyl group at the 17-position on a steroid skeleton may cause sub stantial increases in hormonal activity, University of Western Ontario's C. R. Engel tells the annual meeting of the Chemical Institute of Canada
More Active Hormones Possible Successful 1 7 - m e t h y l a t i o n m a y increase activity of a d r e n a l cortical h o r m o n e s over n a t u r a l c o m p o u n d s TORONTO.-Addition of a methyl group in the 17-position of many hor mones results in interesting changes in hormonal activity. These changes are often substantial increases, as with the 17-a-methyl derivative of progesterone, which is about t w o to three times as active as trie natural hormone when administered by injection. These facts have aroused interest in possible effects of 17-methylation of adrenal cortical hormones, reports Charles T. Engel, University of Western Ontario. Interest was: increased by importance of such steriods as cortisone and 17hydeoxycorticosterone, which also pos sess a substituent (hydroxyl group) in the 17-a position, Engel told the Chemi cal Institute of C a n a d a . Engel and George Just chose 17 amethyldesoxycorticosterone and the 17 homolog of 17-isodesoxycorticosterone as the first representatives of this new group. · Starting material was a steroid which already h a d the a-/?-unsaturated 3 ketonic function, "typical of the hor mones of the testes, the corpus luteum, and the adrenal cortex." Desoxycorticosterone was converted to a mixture of 21-tosyloxypiogesterone and 21-chloroprogesterone; tosylate could be separa ted by rapid chromatography. In presence of potassium methylate, 21-chloroprogesterone undergoes a Faworsky rearrangement affording 9 0 % yields of a mixture of two epimeric methyl 8 4 -3-l
