New structure–activity relationships of A-and D-ring modified steroidal aromatase inhibitors: design, synthesis, and biochemical evaluation

…, C Amaral, G Correia da Silva, T Baptista…

Index: Varela, Carla; Tavares Da Silva, Elisiario J.; Amaral, Cristina; Correia Da Silva, Georgina; Baptista, Teresa; Alcaro, Stefano; Costa, Giosue; Carvalho, Rui A.; Teixeira, Natercia A. A.; Roleira, Fernanda M. F. Journal of Medicinal Chemistry, 2012 ,  vol. 55,  # 8  p. 3992 - 4002

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Citation Number: 30

Abstract

A-and D-ring androstenedione derivatives were synthesized and tested for their abilities to inhibit aromatase. In one series, C-3 hydroxyl derivatives were studied leading to a very active compound, when the C-3 hydroxyl group assumes 3β stereochemistry (1, IC50= 0.18 μM). In a second series, the influence of double bonds or epoxide functions in different positions along the A-ring was studied. Among epoxides, the 3, 4-epoxide 15 showed the ...