Portal de Periódicos da CAPES

Synthesis and preliminary biological evaluation of truncated zoanthenol analogues

2004; Elsevier BV; Volume: 14; Issue: 10 Linguagem: Inglês

10.1016/j.bmcl.2004.02.064

1464-3405

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

Synthesis of heterocyclic compounds

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.