Synthesis and preliminary biological evaluation of truncated zoanthenol analogues |
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Authors: | Hirai Go Oguri Hiroki Hayashi Masahiko Koyama Koji Koizumi Yuuki Moharram Sameh M Hirama Masahiro |
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Institution: | Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. |
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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. |
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