Synthesis and preliminary biological evaluation of truncated zoanthenol analogues

Go Hirai, Hiroki Oguri, Masahiko Hayashi, Koji Koyama, Yuuki Koizumi, Sameh M. Moharram, Masahiro Hirama

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Zoanthamines are a family of marine alkaloids that have complex heptacyclic structures and are reported to be interleukin-6 modulators. While the structure of zoanthamines, especially the ABC-ring portion, is similar to that of steroids, the CDEFG-ring portion, composed of aminoacetal and lactone core, is a unique structural element. In this report, we designed and synthesized ABC-ring 6 and CDEFG-ring 7, which are truncated analogues of the northern and southern hemispheres of zoanthenol 5, respectively, and which incorporate all of the functionality of each hemisphere. A preliminary SAR study suggested that the hydrochloride of the CEFG-ring portion is an active pharmacophore for suppressing the growth of interleukin-6-dependent MH60 cells.

Original languageEnglish
Pages (from-to)2647-2651
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume14
Issue number10
DOIs
Publication statusPublished - May 17 2004
Externally publishedYes

Fingerprint

Interleukin-6
Lactones
Alkaloids
Modulators
Steroids
Growth
zoanthamine
zoanthenol

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Synthesis and preliminary biological evaluation of truncated zoanthenol analogues. / Hirai, Go; Oguri, Hiroki; Hayashi, Masahiko; Koyama, Koji; Koizumi, Yuuki; Moharram, Sameh M.; Hirama, Masahiro.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 14, No. 10, 17.05.2004, p. 2647-2651.

Research output: Contribution to journalArticle

Hirai, G, Oguri, H, Hayashi, M, Koyama, K, Koizumi, Y, Moharram, SM & Hirama, M 2004, 'Synthesis and preliminary biological evaluation of truncated zoanthenol analogues', Bioorganic and Medicinal Chemistry Letters, vol. 14, no. 10, pp. 2647-2651. https://doi.org/10.1016/j.bmcl.2004.02.064
Hirai, Go ; Oguri, Hiroki ; Hayashi, Masahiko ; Koyama, Koji ; Koizumi, Yuuki ; Moharram, Sameh M. ; Hirama, Masahiro. / Synthesis and preliminary biological evaluation of truncated zoanthenol analogues. In: Bioorganic and Medicinal Chemistry Letters. 2004 ; Vol. 14, No. 10. pp. 2647-2651.
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