Azasteroidal mimics – IP 1662

Steroids are one of the most important classes of molecules in our body and perform a number of fundamental biological functions. In order to find new steroidal molecules with desirable biological effects, natural steroids are often modified at several positions, especially in the cyclopentenophenanthrene ring system with heteroatoms or rings. Replacement of one or more carbon atoms in steroids with nitrogen atoms generates new molecules called azasteroids; azasteroids display a variety of biological activities, often free from undesirable or harmful side effects. Several natural and synthetic azasteroids are used for the treatment of steroidal related complications in medicinal biology, including prostate cancer, fungal infections, and hair loss. The challenges in the synthesis of steroids, particularly azasteroids, and the potential of azasteroids as novel drugs has prompted numerous investigations in this field. However, the current synthetic methods leading to azasteroids with one or more nitrogen atoms are very limited. Generally, oxidative cleavage of the steroidal rings is needed to introduce nitrogen atom(s) in order to synthesize azasteroids. Even though several azasteroidal synthesis have been reported, there is still a need for the development of new methodologies as the previous synthetic methods are limited to particular steroidal structures. FIU inventors have designed a five-step process for the synthesis of azasteroidal compounds. The preparation of these new azasteroidal compounds via an intermediate anhydrobase to a steroidal skeleton and the modification of substituents on the steroidal skeletons might provide congeners with useful biological properties. Anne Laure Schmitt Olivier aschmitt@fiu.edu 305-348-5948