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Phenylahistin, a Small Dipeptidic Colchicine-Like Anti-Microtubule Agent: Total Synthesis and SAR Study of the Derivatives

  • Yoshio Hayashi
  • Sumie Orikasa
  • Koji Tanaka
  • Kaneo Kanoh
  • Yoshiaki Kiso
Part of the American Peptide Symposia book series (APSY, volume 7)

Abstract

Phenylahistin (1), a fungal metabolite from Aspergillus ustus NSC-F038, belongs to a new class of peptidic colchicine-like microtubule-binding agents that exhibits cytotoxic activity against a wide variety of tumor cell lines [1]. (-)-Phenylahistin (-)-1, a diketopiperazine derivative, consists of L-phenylalanine and a unique isoprenylated dehydrohistidine residue with a quaternary carbon at the 5-position of the imidazole ring. To develop more potent anti-tumor agents based on this diketopiperazine derivative, it is important to elucidate the structural components necessary for the anti-microtubule activity of (-)-1. The total synthesis of 1 will establish the synthetic route for its derivatives.

Keywords

Synthetic Route Imidazole Ring Total Synthesis Aromatic Amino Acid Residue High Cytotoxic Activity 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    Kanoh, K., Kohno, S., Katada, J., Hayashi, Y. Muramatsu, M., Uno, I. Biosci. Biotechnol. Biochem. 63, 1130–1133 (1999).PubMedCrossRefGoogle Scholar
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    Kanoh, K., Kohno, S., Katada, J., Takahashi, J., Uno, I., Hayashi, Y. Bioorg. Med. Chem. 7, 1451–1457 (1999).PubMedCrossRefGoogle Scholar
  3. 3.
    Hayashi, Y., Orikasa, S., Tanaka, K., Kanoh, K., Kiso, Y. J. Org. Chem. 65, 8402–8405 (2000).PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media Dordrecht 2001

Authors and Affiliations

  • Yoshio Hayashi
    • 1
  • Sumie Orikasa
    • 1
  • Koji Tanaka
    • 1
  • Kaneo Kanoh
    • 2
  • Yoshiaki Kiso
    • 1
  1. 1.Department of Medicinal Chemistry, Center for Frontier Research in Medicinal ScienceKyoto Pharmaceutical UniversityKyotoJapan
  2. 2.Shimizu LaboratoriesMarine Biotechnology InstituteShizuokaJapan

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