Novel anti-viability ceramide analogs: design, synthesis, and structure-activity relationship studies of substituted (S)-2-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamides

Bioorganic & Medicinal Chemistry
Jiawang LiuMaryam Foroozesh

Abstract

A group of novel L-serinamides, substituted (S)-2-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamides (3a-o) and substituted (S)-2-(benzylamino)-3-hydroxy-N-tetradecyl propanamides (4c, 4i, 4l, and 4o), were synthesized as potential anti-tumor lead compounds. In vitro cell viability assay results indicate treatment with 3a-o compounds resulted in significant inhibition of cell viability in the chemoresistant breast cancer cell line, MCF-7TN-R. Compounds 3i and 3l, both ortho-substituted analogs, show the greatest efficacy with IC50 values of 10.3 microM and 12.5 microM, respectively. The SAR analysis indicate that the imine functional group of 3a-o is critical for the cellular anti-viability effect, and the partial atomic charge (PAC) value of imine C atom is a valuable structural parameter for predicting the activity of these ceramide analogs.

References

Jan 18, 2003·Biochimica Et Biophysica Acta·Benjamin J PettusYusuf A Hannun
Sep 1, 2006·Chemistry and Physics of Lipids·Santiago GrijalvoGemma Fabriàs
Sep 2, 2008·Chemistry and Physics of Lipids·Carmen BediaGemma Fabriás
Mar 13, 2009·Carcinogenesis·Susanne SchiffmannSabine Grösch
Jun 18, 2009·Molecular Cancer Research : MCR·David E ModrakDavid V Gold

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Citations

Jan 25, 2014·Bioorganic & Medicinal Chemistry·Adharsh P PonnapakamBarbara S Beckman
Aug 8, 2013·Future Medicinal Chemistry·Jiawang LiuMaryam Foroozesh
Jul 26, 2018·Anti-cancer Drugs·Tulasi PonnapakkamMaryam Foroozesh
Apr 4, 2015·Biological Chemistry·Mark KesterMylisa R Parette
Aug 18, 2021·Toxicology Reports·Tulasi PonnapakkamMaryam Foroozesh

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