A new synthesis of 4'-resveratrol esters and evaluation of the potential for anti-depressant activity

  • Bioorg Med Chem Lett. 2013 May 15;23(10):2941-4. doi: 10.1016/j.bmcl.2013.03.046.
Mark J Acerson  1 ,  Kimberly M Fabick ,  Yong Wong ,  Crystal Blake ,  Edwin D Lephart ,  Merritt B Andrus
Affiliations
  • 1. Department of Chemistry, Brigham Young University, Provo, UT 84602, USA.
PMID: 23582778 DOI: 10.1016/j.bmcl.2013.03.046
Abstract

The 4'-ester analog of the disease preventative resveratrol 1 (RV), 4'-acetyl-RV 2 along with 4'-pivaloate 13 and benzoate 14 RV were synthesized. The previously developed palladium catalyzed decarbonylative Heck coupling was used to assemble the stilbene core together with 3,5-dibenzyl protected phenol intermediates that allowed for efficient coupling and deprotection using boron trifluoride etherate. Studies with Long-Evans rats were performed to establish safety, toxicity, and behavioral parameters. In addition, the Porsalt forced-swim test was used to demonstrate anti-depressant activity.