Scalable laboratory synthesis of potent antioxidants in the resveratrol family
Scalable laboratory synthesis of potent antioxidants in the resveratrol family
Simple and expedited syntheses of multiple resveratrol- based compounds and analogs. This technology provides a general synthetic strategy to make different members of the resveratrol class. The approach is based on the use of a common building block in a variety of highly selective, reagent-controlled reaction cascades that concisely generate analogues with complete chemoselectivity.
New York, NY, United States
Overview Comments Tagged publications (1)

Background 

Resveratrol, an organic polyphenol antioxidant naturally found in red wine, has been targeted for use in a wide array of applications ranging from cosmetic treatments to cancer therapies. This is due to resveratrol’s distinct anti-inflammatory, UVB-protective, anti-aging, and tumor suppressant biological properties. By extension, other chemical compounds structurally similar to resveratrol are sought after for their potential to demonstrate even better utility toward these applications. However, extracting resveratrol or similar polyphenol compounds from natural sources in workable quantity is cumbersome and has hindered research. This technology describes a concise, scalable synthetic strategy for creating a diverse array of these compounds in the laboratory, thereby making investigation of these molecules possible for use in product design and development.

Simple and expedited syntheses of multiple resveratrol- based compounds and analogs

This technology provides a general synthetic strategy to make different members of the resveratrol class. The approach is based on the use of a common building block in a variety of highly selective, reagent-controlled reaction cascades that concisely generate analogues with complete chemoselectivity. The technology can thus be used to reliably make large quantities of both natural and non-natural resveratrol variants. Allowing for a wide array of diverse structures to be produced succinctly makes this approach highly applicable to rational molecule design. Additionally, structures designed using this technology can easily be optimized to generate molecules that elicit the desired potency and efficacy for the intended application.

The synthetic strategy embodied in the technology has been tested to make resveratrol and numerous natural and non-natural isosteres, all of which have had their structure validated through 1H-NMR, 13C-NMR, mass spectrometry, and infrared spectrometry techniques.

Lead Inventor:

Scott A. Snyder, Ph.D.

Applications:

  • Selective synthesis of resveratrol-based compounds for biological activity evaluation 
  • Synthesis of potential drug candidates for the treatment of diseases, such as: diabetes, cardiovascular disease, cancer; Alzheimer’s disease, and optic neuritis 
  • Synthesis of compounds as potential potent anti-aging agents 

Advantages:

  • Speed and ease of synthesis of a diverse array of resveratrol-based polyphenolic compounds 
  • Allows optimization of molecules based on rational drug design 
  • Large quantity production of high-purity resveratrol-based natural products and natural product-like analogs using simple reagents 

Patent information:

Patent Pending (WO/2009/038731)

Licensing Status:

Available for licensing and sponsored research support

Tech Ventures Reference: IR M08-006 and IR M09-015

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