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Perylenequinones: Isolation, Synthesis, and Biological Activity

  1. Carol A. Mulrooney1,2,
  2. Erin M. O'Brien1,3,
  3. Barbara J. Morgan1,4,
  4. Marisa C. Kozlowski1

Article first published online: 23 MAY 2012

DOI: 10.1002/ejoc.201200184

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2012, Issue 21, pages 3887–3904, July 2012

Additional Information

How to Cite

Mulrooney, C. A., O'Brien, E. M., Morgan, B. J. and Kozlowski, M. C. (2012), Perylenequinones: Isolation, Synthesis, and Biological Activity. Eur. J. Org. Chem., 2012: 3887–3904. doi: 10.1002/ejoc.201200184

Author Information

  1. 1

    Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA

  2. 2

    Current address: Broad Institute, Boston, Massachusetts, USA

  3. 3

    Current address: Millennium, The Takeda Oncology Company, Boston, Massachusetts, USA

  4. 4

    Current address: Goodwin Proctor, Boston, Massachusetts, USA

Publication History

  1. Issue published online: 11 JUL 2012
  2. Article first published online: 23 MAY 2012
  3. Manuscript Received: 16 FEB 2012

Funded by

  • National Science Foundation (NSF). Grant Numbers: CHE-0616885, CHE-0911713
  • National Institutes of Health (NIH). Grant Number: CA-109164

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Keywords:

  • Total synthesis;
  • Natural products;
  • Structure–activity relationships;
  • Photodynamic therapy;
  • Quinones;
  • Biaryls

Abstract

The perylenequinones are a class of natural products characterized by a pentacyclic conjugated chromophore giving rise to photoactivity. Potentially useful light-activated biological activity, targeting protein kinase C (PKC), has been identified for several of the natural products. Recently discovered new members of this compound class, as well as several related phenanthro-perylenequinones, are reviewed. Natural product modifications that improve biological profiles are outlined, as well as avenues for the total synthesis of analogs not available from the natural product series. An overview of structure/function relationships is provided.

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