ORR,DE
3300
Steroids.
LA
Roz, AND BOWERS
CCLXV.'
Studies in Cyano Steroids. Unsaturated 2-Cyano Steroids
JAMES C. O R R ,ARCELIA ~ DE
LA
Roz,
AND
VOL. 29
III.2
A. BOWERS
Research Laboratories, Syntex, S.A., Mexico, D.F., Mexico Received June 18, 1964 The preparation of 2-cyano-A'-3-keto steroids and their corresponding A4-analogs in the androstane and corticoid series is described. A series of 2-cyano-A2-androstenes was also prepared. These constitute a new class of biologically important compounds and demonstrate for the first time that the cyano group can be an important potentiating group for biological activity in steroids.
Earlier studies from t h e ~ e ~ and - ~other laboratories7f8 Nc& ....R have led to the preparation of various cyano-substituted steroid hormones. However, in every case the introduction of the nitrile group led to a decrease in biological O k O H activity. This paper describes an extension to a numla, R=Me 2 a, X= H; R: Me ber of A'-2-cyano hormone analogs as well as the prepab, R: Me; A4-doublc bond b, X = H; RzMe; A4-doublc bond ration of a series of 2-cyano-A2-androstenes. The C , R:H; A4-double bond c, X = A c ; R = H , A4-double bond Iatter compounds are the first cyano steroids to demonstrate high biological activity and represent a new class of modified androgens with good myotrophic activity. ...Q> HO-Cp & A1-2-Cyano-3-keto steroids have not been reported previously. Introduction of a double bond in the 1position of 2a-cyano-17p-hydroxy-17a-methyl-5a-an- 0 NC 0. drostan-3-one5 ( l a ) was readily accomplished by reac3 4 a, y=
