3 years ago

Synthesis and biological evaluation of some undecanone derivatives

Trimurtulu Golakoti, Suryachandra Rao Ravada, Bharani Meka, Harikrishna Kancharla

Abstract

The total synthesis of Ardisinone E [15, 1-(2,4,6-trihydroxy phenyl)-11-(2-hydroxyphenyl)-undecan-1-one], a natural diarylundecanone, isolated from Ardisia arborescens, was accomplished along with 16 new diarylundecanone analogs (18ap), by modified Wittig reaction. The structures of the compounds were confirmed by 1H, 13C and mass spectral data. Compound 15 showed potent cytotoxic activity with an ED50 of 4.19 µg/mL in brine shrimp lethality assay model. Compounds 18c, 18e, 18j, 18k, 18l, and 18m exhibited strong anti-oxidant activity with IC50 values of 18.75, 12.28, 18.35, 11.04, 12.05, and 11.32 µg/mL, respectively, in NBT free radical assay. Compounds 18e, 18k, and 18m also showed significant 5-lipoxyganase enzyme inhibitory potential with IC50 values of 12.8, 15.23, and 15.23 µg/mL, respectively.

Publisher URL: https://link.springer.com/article/10.1007/s00044-017-2006-7

DOI: 10.1007/s00044-017-2006-7

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