A novel route to a 4-amino steroid: MDL 19687

Synthesis of marine brominated alkaloid amathamide F: a palladium-catalyzed enamide synthesis

“…5 Since, our aim was to reduce the nitro group of compound 19 without concomitant reduction of the double bond, it was subjected to hydrogenation in presence of Lindlar catalyst (Scheme 2). 20 Unfortunately this reaction did not work. We then turned our attention to Fe-powder in Ac 2 O/AcOH 21 as a potential cock-tail to achieve the goal of selective reduction over 19.…”

“…We then turned our attention to Fe-powder in Ac 2 O/AcOH 21 as a potential cock-tail to achieve the goal of selective reduction over 19. It was highly gratifying to note that indeed this condition worked well furnishing a chromatographically separable cis (20) and trans (21) N-acetylated enamines, albeit in modest yields. At this juncture, direct coupling between compound 21 and N-methyl-L-proline would furnish the N-acetyl derivative of amathamide E (3), however it could not be achieved (Scheme 2).…”

Facile synthesis of two azete-steroid derivatives and theoretical evaluation of its interaction with the aromatase enzyme

“…Other studies showed the synthesis of amino-steroids through a nitro-steroids derivatives reduction [24]. Also, a report showed an amination of steroids using palladium as catalyst [25]. Other data showed the synthesis of some amino-steroid derivatives via Mannich reaction; it is noteworthy that structural chemistry of these compounds [26] involves an activated methyl group in ring A.…”

Steroidal CYP17 Inhibitors for Prostate Cancer Treatment: From Concept to Clinic

“…The 17-aza derivative 94 inhibited human CYP17 with an IC 50 value of 4.9 µM [123]. Compound 95 inhibited both 5α-reductase and CYP17 with k i values of 27 and 14 nM, respectively [124]. The oxime 96 was also a dual inhibitor with the ability to reduce serum and prostatic T and DHT concentrations in vivo [125].…”