147802-68-4

Upstream product

• 262293-86-7 3-Benzyloxy-17-hydroxyestra-1,3,5⁽¹⁰⁾-trien-16-one oxime 
• 53-16-7 Estrone 
• 858-98-0 3-benzyloxyestra-1,3,5⁽¹⁰⁾-trien-17-one 
• 100-44-7 benzyl chloride 
• 262293-85-6 3-(benzyloxy)-16-(hydroxyimino)-estra-1,3,5⁽¹⁰⁾-trien-17-one 

Downstream Products

• 147802-69-5 3-Benzyloxy-17-hydroxy-16,17-secoestra-1,3,5⁽¹⁰⁾-triene-16-nitrile 
• 1173915-25-7 C₂₅H₂₇N₃O 

Relevant academic research and scientific papers

Synthesis and biological activity of new 16, 17-secoestrone derivatives

Starting from estrone 3-benzyloxy-17β-hydroxyestra-1,3,5(10)-trien-16-one oxime (3b) was synthesized, which underwent Beckmann fragmentation giving the 3-benzyloxy-17-oxo-16,17-secoestra-1,3,5(10)-triene-16-nitrile (4b). Sodiumb borohydride reduction of this compound afforded 3-benzyloxy-17-hydroxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile (5b). The deprotection of the 3-hydroxy group was achieved by action of hydrogen upon derivatives 4b and 5b in presence of Pd/C as a catalyst, yielding 3-hydroxy-17-oxo-16,17-secoestra-1,3,5(10)-triene-16-nitrile (4a) and 3,17-dihydroxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile (5a). In biological tests on experimental animals, compounds 4a, 4b, 5a and 5b showed virtually a complete loss of estrogenic activity, whereas compounds 4a, 5a and 5b exhibited moderate antiestrogenic effect.