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Koufaki, M. et al.

Maria Koufaki, Christina Kiziridi, Xanthippi Alexi, Michael N. Alexis,

Design and synthesis of novel neuroprotective 1,2-dithiolane/chroman hybrids.

Novel 1,2-dithiolane/chroman hybrids bearing heterocyclic rings such as 1,2,4- and 1,3,4-oxadiazole, 1,2,3-triazole and tetrazole were designed and synthesized. The neuroprotective activity of the new analogues was tested against oxidative stress-induced cell death of glutamate-challenged HT22 hippocampal neurons. Our results show that bioisosteric replacement of amide group in 2-position of the chroman moiety, by 1,3,4-oxadiazole did not affect activity. However, analogue 5 bearing the 1,2,4-oxadiazole moiety showed improved neuroprotective activity. The presence of nitrogen heterocycles strongly influences the neuroprotective activity of 5-substituted chroman derivatives, depending on the nature of heterocycle. Replacement of the amide group of the first generation analogues by 1,2,4-oxadiazole or 1,2,3-triazole resulted in significant improvement of the activity against glutamate induced oxidative stress.[1]

References

Design and synthesis of novel neuroprotective 1,2-dithiolane/chroman hybrids. Koufaki, M., Kiziridi, C., Alexi, X., Alexis, M.N. Bioorg. Med. Chem. (2009) [Pubmed]

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