Bioorganic & Medicinal Chemistry Letters 2004-05-17

Synthesis and preliminary biological evaluation of truncated zoanthenol analogues.

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

Index: Bioorg. Med. Chem. Lett. 14 , 2647, (2004)

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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.