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Insights into the Synthesis of Steroidal A-Ring Olefins
Varela, Carla M.; Roleira, Fernanda M. F.; Costa, Saul C. P.; Tinto, Alexandra S. C. T.; Martins, Ana I. O. S.; Carvalho, Rui A.; Teixeira, Natércia A.one (5), from the D1-3-keto enone, (5a,17b)-3-oxo-5-androst-1-en-17-yl acetate (1), through a strategy involving the reaction of D1-3-hydroxy allylic alcohol, 3b-hydroxy-5a-androst-1-en-17b-yl acetate (2), with SOCl2 , was revisited in order to prepare and biologically evaluate 5 as aromatase inhibitor for breast cancer treatment. Surprisingly, the followed strategy also afforded the isomeric D2-olefin 6 as a b...
New steroidal 17b-carboxy derivatives present anti-5a-reductase activity and an...
Amaral, Cristina; Varela, Carla; Correia-da-Silva, Georgina; da Silva, Elisário Tavares; Carvalho, R. A.; Costa, Saul C. P.; Cunha, Sara C.The androgens testosterone (T) and dihydrotestosterone (DHT), besides playing an important role in prostate development and growth, are also responsible for the development and progression of benign prostate hyperplasia (BPH) and prostate cancer. Therefore, the actions of these hormones can be antagonized by preventing the irreversible conversion of T into DHT by inhibiting 5a-reductase (5a-R). This has been a ...
Ultrasound assisted remote functionalization of non-activated carbon atoms: eff...
Costa, Saul C. P.; Moreno, M. J. S. Miranda; Melo, M. Luísa Sá e; Neves, André S. CamposUltrasonic irradiation of bromohydrins in the presence of (diacetoxyiodo)benzene and I2 generates alkoxyl radicals which lead in situ to intramolecular hydrogen abstraction on the C-19 non-activated carbon atoms in steroids producing tetrahydrofurans selectively in very good yields. Photolysis was less effective in promoting such conversions. ; http://www.sciencedirect.com/science/article/B6THS-3YF4638-1R/1/...
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