Get access

Diversity Through a Branched Reaction Pathway: Generation of Multicyclic Scaffolds and Identification of Antimigratory Agents

Authors

  • Dr. Zhiming Wang,

    1. Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095-1569 (USA), Fax: (+1) 310-206-3722
    2. School of Chemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, (P.R. China)
    Search for more papers by this author
  • Dr. Sabrina Castellano,

    1. Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095-1569 (USA), Fax: (+1) 310-206-3722
    Search for more papers by this author
  • Dr. Sape S. Kinderman,

    1. Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095-1569 (USA), Fax: (+1) 310-206-3722
    Search for more papers by this author
  • Christian E. Argueta,

    1. Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060 (USA), Fax: (+1) 860-486-2981
    Search for more papers by this author
  • Dr. Anwar B. Beshir,

    1. Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060 (USA), Fax: (+1) 860-486-2981
    Search for more papers by this author
  • Prof. Gabriel Fenteany,

    Corresponding author
    1. Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060 (USA), Fax: (+1) 860-486-2981
    • Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269-3060 (USA), Fax: (+1) 860-486-2981
    Search for more papers by this author
  • Prof. Ohyun Kwon

    Corresponding author
    1. Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095-1569 (USA), Fax: (+1) 310-206-3722
    • Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095-1569 (USA), Fax: (+1) 310-206-3722
    Search for more papers by this author

Abstract

A library of 91 heterocyclic compounds composed of 16 distinct scaffolds has been synthesized through a sequence of phosphine-catalyzed ring-forming reactions, Tebbe reactions, Diels–Alder reactions, and, in some cases, hydrolysis. This effort in diversity-oriented synthesis produced a collection of compounds that exhibited high levels of structural variation both in terms of stereochemistry and the range of scaffolds represented. A simple but powerful sequence of reactions thus led to a high-diversity library of relatively modest size with which to explore biologically relevant regions of chemical space. From this library, several molecules were identified that inhibit the migration and invasion of breast cancer cells and may serve as leads for the development of antimetastatic agents.

Get access to the full text of this article

Ancillary