147900-22-9

Usage

InChI:InChI=1/C23H26O5/c1-4-21(28-13(2)24)23-10-7-14(25)11-18(23)19(26)12-15-16-5-6-20(27)22(16,3)9-8-17(15)23/h1,11,15-17,21H,5-10,12H2,2-3H3/t15-,16-,17-,21?,22-,23-/m0/s1

Upstream product

• 147900-21-8 (19R)-19-ethynyl-19-acetoxy-3β-hydroxyandrost-5-en-17-one 
• 147900-20-7 (19S)-19-ethynyl-19-acetoxy-3β-hydroxyandrost-5-en-17-one 

Relevant academic research and scientific papers

A time-dependent inactivation of aromatase by 19-substituted androst-4-ene-3,6, 17-triones

Diastereomeric (19S)- and (19R)-19-ethynyl-19-acetoxy derivatives of androst-4-ene-3,6,17-trione (AT) (9 and 10) and 19,19-difluoro AT (12) were synthesized. The 19,19-difluoro compound (12) was an effective competitive inhibitor of human placental aromatase with an inhibition constant (k:) of 1.8 fiM but the acetylenic 9 and 10 were poor inhibitors of the enzyme with kis of 75 and 67 ·M, respectively. Inhibitor 12 caused a time-dependent, biphasic loss of aromatase activity in the presence of reduced nicotinamide-adenine-dinucleotide phosphate (NADPH) in air, whereas the other two caused a time-dependent, pseudo-first-order inactivation of the activity with rate constants for inactivation of 0.250, 0.077, and 0.065 min-1 for steroids 12, 9, and 10. NADPH was required for the time-dependent inactivation, and the substrate androst-4-ene-3,17-dione prevented it.L,-Cysteine did not protect aromatase from the inactivation. (Steroids 58:40-46, 1993).