Nucleophilic vinylic “addition-elimination” substitution reaction of 3β-acetoxy-17-chloro-16-formylandrosta-5,16-diene: A novel and general route to 17-substituted steroids. Part 1 - synthesis of novel 17-azolyl-Δ16 steroids; inhibitors of 17α-hydroxylase/17, 20-lyase (17α-lyase)

Synthesis and biological evaluation of esters of 16-formyl-17-methoxy-dehydroepiandrosterone derivatives as inhibitors of 5α-reductase type 2

“…To a solution of 17-chloro-16-formylandrost-5,16-dien-3b-yl acetate ( Figure 2) (2) (200 mg, 0.53 mmol) in dimethylformamide under nitrogen atmosphere, 0.5 M sodium methoxyde in methanol (1.3 mL, 1.2 meq) was added, and the mixture was stirred for 30 min at room temperature. The reaction mixture was then added into 20 mL of ice, and the solid obtained was filtered by vacuum and washed three times with cold water 13 . The yellow crude product was purified by flash column chromatography (FCC, Florisil Õ 60-100 hexane: AcOEt 65:25) 13 .…”

“…The reaction mixture was then added into 20 mL of ice, and the solid obtained was filtered by vacuum and washed three times with cold water 13 . The yellow crude product was purified by flash column chromatography (FCC, Florisil Õ 60-100 hexane: AcOEt 65:25) 13 .…”

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

“…In 1996, Njar et al reported the first steroidal inhibitors of CYP17 bearing a heterocyclic moiety bound to C17 by a nitrogen atom [101], which included compounds 53-55 (Fig. 5, Table 2, entries [19][20][21], among which the imidazolyl derivative 53 was found to be the most promising [101][102][103][104]. Later, in 2005, the same group reported the synthesis of galeterone 4 and its Δ 4 -3-keto derivative 56 (Fig.…”

A new pregnenolone analogues as privileged scaffolds in inhibition of CYP17 hydroxylase enzyme. Synthesis and in silico molecular docking study

“…In addition, computational studies established that a good inhibitor should possess a sufficiently large hydrophobic core, comparable to a steroid molecule, and bear electronegative groups at its external positions [10,11]. Therefore, recently several nitrogen containing steroidal compounds containing fiveor six-membered 17b-exo-heterocycles (preferably nitrogen containing), such as steroidal azoles [12,13] have been developed for the treatment of prostate cancer, including abiraterone acetate (Zytiga) 1 [14,15], VN/124-1 galeterone (2) [16][17][18], which is currently undergoing phase I/II clinical trials for the treatment of chemotherapy naive castration-resistant prostate cancer (CRPC) [19,20] and VN/85-1 (3) [21,22] (Fig. 1), which reduce circulating androgen levels through inhibition of CYP17 [23].…”