89593-30-6Relevant academic research and scientific papers
Synthesis and evaluation of novel 4-amino-4,6-androstadiene-3,17-dione: An analog of formestane
Sharma, Sanjay K.,Zheng, Weizhong,Joshua, Alummoottil V.,Abrams, Douglas N.,McEwan, Alexander J.B.
, p. 5563 - 5566 (2008)
Synthesis of 4-amino-4,6-androstadiene-3,17-dione 7, an analog of formestane used in breast cancer therapy as an aromatase inhibitor, from 4-acetoxy-4-androstene-3,17-dione 2 is described. This is the first report of a 4-amino diene (4,6) system in this series of molecules. The new (7) and reported molecules were screened by the National Cancer Institute (NCI, Bethesda, USA) for in vitro antitumor activity against 60 human cancer cell lines. Molecule 7 showed best activity against breast cancer cell line (MCF-7).
C-6α- vs C-7α-Substituted Steroidal Aromatase Inhibitors: Which Is Better? Synthesis, Biochemical Evaluation, Docking Studies, and Structure-Activity Relationships
Roleira, Fernanda M. F.,Varela, Carla,Amaral, Cristina,Costa, Saul C.,Correia-Da-Silva, Georgina,Moraca, Federica,Costa, Giosuè,Alcaro, Stefano,Teixeira, Natércia A. A.,Tavares Da Silva, Elisiário J.
, p. 3636 - 3657 (2019/04/26)
C-6α and C-7α androstanes were studied to disclose which position among them is more convenient to functionalize to reach superior aromatase inhibition. In the first series, the study of C-6 versus C-7 methyl derivatives led to the very active compound 9 with IC50 of 0.06 μM and Ki = 0.025 μM (competitive inhibition). In the second series, the study of C-6 versus C-7 allyl derivatives led to the best aromatase inhibitor 13 of this work with IC50 of 0.055 μM and Ki = 0.0225 μM (irreversible inhibition). Beyond these findings, it was concluded that position C-6α is better to functionalize than C-7α, except when there is a C-4 substituent simultaneously. In addition, the methyl group was the best substituent, followed by the allyl group and next by the hydroxyl group. To rationalize the structure-activity relationship of the best inhibitor 13, molecular modeling studies were carried out.
The Synthesis of 4-Hydroxyandrost-4-ene-3,17-dione and other Potential Aromatase Inhibitors
Mann, John,Pietrzak, Barbara
, p. 2681 - 2685 (2007/10/02)
We describe novel syntheses of 4-hydroxyandrost-4-ene-3,17-dione (Ia) and related compounds, some containing fluorine.In addition we provide further evidence of the general tendency of 2- and 6-substituted androst-4-ene-3,17-diones to undergo rearrangement reactions, and thus provide new routes to 6-fluoro- and 2,6-difluoro-derivatives.Several of these compounds are potent aromatase inhibitors.
