Synthesis and biological evaluation of heterocyclic analogues of pregnenolone as novel anti-osteoporotic agents


Maurya SW, Dev K, Singh KB, Rai R, Siddiqui IR, Singh D, Maurya R




Bioorg Med Chem Lett . 2017 Mar 15;27(6):1390-1396.

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The structural modifications of pregnenolone have been described via the introduction of heterocyclic moieties at C-17 position by limiting the acyl group.

Novel heterocyclic analogues of pregnenolone have been synthesized by using Friedlander and Claisen-Schmidt reactions, and the synthesized compounds were evaluated for their osteogenic activity.

Among the synthesized derivatives, four compounds showed significantly increased ALP activity. Among all four active compounds, the novel compound 3a has shown significant bone matrix mineralization and mRNA expressions of osteogenic marker genes, BMP2, RUNX-2 and OCN at 1pM concentration.

Structural formula of pregnenolone; the three marked locations are the places where modifications can be made to obtain pregnenolone analogs. (Source: modified from Maurya SW et al. 2017)

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