849791-82-8Relevant articles and documents
Neurosteroid analogues: Synthesis of 6-aza-allopregnanolone
Kasal, Alexander,Matyá?, Libor,Budě?ínsky, Milo?
, p. 2269 - 2278 (2007/10/03)
An efficient synthesis of 6-azapregnane derivatives and their biological activity is described. The nitrogen was introduced into the B ring using Beckmann rearrangement of the (E)-oxime of 6-oxo-B-nor-5α-pregnane derivatives. The required 3α-hydroxyl was produced either by solvolysis of the corresponding 3β-mesyloxy group or by the Meerwein-Ponndorf-Verley reduction of the 3-oxo group; this reduction could be carried out selectively with an unprotected 3,20-dioxo derivative. The binding of the 6-aza-steroids to the γ-aminobutyric acid receptor (GABAA) was measured using [35S]-tert-butyl-bicyclo[2.2.2]phosphorothionate (TBPS) and [ 3H]flunitrazepam. The only analogue to be slightly active was that lacking any oxygen function in position 3.