A Concise Route to 19-Nor-10-azasteroids, a New Class of Steroid 5α-Reductase Inhibitors. 3.¹ Synthesis of (+)-19-Nor-10-azatestosterone and (+)-17β-(Acetyloxy)-(5β)-10-azaestr-1-en-3-one

Selective non-steroidal inhibitors of 5α-reductase type 1

“…The first inhibitors have been therefore designed by modifying the structure of natural substrates, including the substitution of one carbon atom of the A or B ring of the steroids by an heteroatom, leading to the discovery of potent inhibitors of human 5␣-reductase such as 4-azasteroids (among which finasteride, marketed for the treatment of BPH) [30][31][32], 6-azasteroids [33,34], 10-azasteroids [35][36][37][38][39], and steroidal carboxylic acid inhibitors [40][41][42][43] (Scheme 2). The kinetic mechanism by which T is reduced to DHT is believed to proceed via a preferentially ordered binding of the substrate and release of DHT from the enzyme.…”

Synthesis of 3-Substituted Derivatives of 2,2,6,6-Tetramethylpiperidine-N-alkoxyamine Ethers: Novel Alkoxyamine Building Blocks

“…9,11 These compounds represent highly functionalized alkoxyamines, which provide countless opportunities for further transformation. As to biologically active compounds, bicyclic lactones, 15 azasteroids, 16 pyrindinones, 17 lactames, 18 or enantiopure piperidines 18 may be attractive targets. With regard to the mentioned polymer light stabilizers, 12d might already be an interesting compound.…”

Synthesis, Spectral Characterization, andIn VitroCytotoxicity of N-2′-Hydroxyethyl-Substituted Azacholestanes Prepared from 6-Oxocholestanes by Modified Schmidt Reaction

“…During the last decade, a number of azasteroids have been synthesized as 5 -reductase inhibitors [23][24][25][26][27]. Guarna and coworkers have also synthesized and explored the biological application of a novel class of potent azasteroidal inhibitors having nuclear nitrogen atom at position C-10 of the steroidal ketones [28]. Several reports pertaining with the preparation of azasteroids have been mentioned in the literature [29][30][31][32].…”