Novel synthesis of steroidal oximes and lactams and their biological evaluation as antiproliferative agents
2017; Elsevier BV; Volume: 122; Linguagem: Inglês
10.1016/j.steroids.2017.03.008
ISSN1878-5867
AutoresRoxana Martínez-Pascual, Socorro Meza‐Reyes, José Luis Vega-Báez, Penélope Merino‐Montiel, José M. Padrón, Ángel Mendoza, Sara Montiel‐Smith,
Tópico(s)Phytochemistry and Bioactive Compounds
ResumoA novel three-step methodology to obtain 6a-aza-B-homo steroidal lactams has been developed starting from the easily available cholesterol and pregnenolone. In addition, a new procedure for the synthesis of a 6a-aza-B-homo steroidal lactam analog of vespertilin, starting from diosgenin has been established. In both synthetic pathways, the key intermediate is a hydroxyimino derivative obtained in a one- or two-step sequence from the starting materials. These methods avoid the use of hazardous oxidant agents in the process. The new steroidal oximes and lactams were examined for their antiproliferative activities against several tumor cell lines. The 6,23-dihydroxyimino derivative exhibited the highest activity with GI50 values of 11–22 µM.
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