Salvianolic acid F
The role of our hybrid molecules, an analogue of Salvianolic acid F, in compelling the glioma cells towards apoptosis by specifically perturbing the concentration of glutathione along with caspase 6.
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24 months(2-8C).
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Eur. J. Org. Chem., 2016, 36:5941–9.
Divergent Synthesis of Styryl–Cinnamate Hybrid Analogues Inspired by the Natural Product Salvianolic Acid F as a Premise To Investigate Their Anticancer Activity and Its Metabolomic Profiling[Reference:
WebLink]
The natural product Salvianolic acid F- inspired protecting-group-free synthesis of hydroxylated styryl-cinnamate hybrids (C6-C2-C6-C3 unit) has been achieved by step-economical route via sequential double C-C bond formation in one pot.
METHODS AND RESULTS:
The present method involves multiple reactions (Perkin-condensation/ decarboxylation-Heck cross-coupling reactions) using simple precursors (i.e. hydroxylated benzaldehyde, arylacetic acid and acrylic acid derivatives) in one pot which yields desired unnatural small hybrid molecules (1-12) in varying yields of 35-65%with E-selectivity under microwave irradiation whereas the reported conventional route for synthesis of Salvianolic acid F itself requires six steps with an overall yield of 10.0% besides tedious separation of E/Z isomers that arise from Wittig reaction.Apart from an economical synthesis and products diversity, we herein report the potential of some hybrid molecules (3,8,10 and 11), with the catecholic core, to selectively inhibit glioma cells. The intrinsic mode of action (MOA) for our lead molecule involving caspase 6 and quinonemethide pathway is also reported based on 1HNMR-guided metabolomic profiling.
CONCLUSIONS:
We emphatically demonstrate the role of our hybrid molecules, an analogue of Salvianolic acid F, in compelling the glioma cells towards apoptosis by specifically perturbing the concentration of glutathione along with caspase 6.
