Medicinal Chemistry Research

, Volume 26, Issue 12, pp 3106–3124 | Cite as

Synthesis and biological evaluation of some undecanone derivatives

  • Bharani Meka
  • Suryachandra Rao Ravada
  • Harikrishna Kancharla
  • Trimurtulu Golakoti
Original Research
  • 106 Downloads

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.

Keywords

Ardisinone Diarylundecanone Ardisia arborescens 5-lipoxyganase Brine shrimp 

Notes

Acknowledgements

The authors thank Sri G. Ganga Raju, Chairman, Mr. G. Rama Raju, Director and Mr. B. Kiran, CEO, Laila Nutraceuticals for their encouragement, PDT in vitro division for the bioactivity studies.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no competing interests.

Supplementary material

44_2017_2006_MOESM1_ESM.docx (22.6 mb)
Supplementary Information

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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  1. 1.Laila Impex R & D CentreVijayawadaIndia

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