Synthesis and preliminary biological evaluation of truncated zoanthenol analogues

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

doi:10.1016/j.bmcl.2004.02.064

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 journal › Article

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 language	English
Pages (from-to)	2647-2651
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	14
Issue number	10
DOIs	https://doi.org/10.1016/j.bmcl.2004.02.064
Publication status	Published - May 17 2004
Externally published	Yes

All Science Journal Classification (ASJC) codes

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

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Hirai, G., Oguri, H., Hayashi, M., Koyama, K., Koizumi, Y., Moharram, S. M., & Hirama, M. (2004). Synthesis and preliminary biological evaluation of truncated zoanthenol analogues. Bioorganic and Medicinal Chemistry Letters, 14(10), 2647-2651. https://doi.org/10.1016/j.bmcl.2004.02.064

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AU - Moharram, Sameh M.

AU - Hirama, Masahiro

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