TY - JOUR
T1 - Synthesis and preliminary biological evaluation of truncated zoanthenol analogues
AU - Hirai, Go
AU - Oguri, Hiroki
AU - Hayashi, Masahiko
AU - Koyama, Koji
AU - Koizumi, Yuuki
AU - Moharram, Sameh M.
AU - Hirama, Masahiro
N1 - Funding Information:
We thank Prof. D. Uemura (Nagoya University) for the generous gift of zoanthamine 1 and norzoanthamine 2 . This work was supported by the Ministry of Education, Science, Sports and Culture (Japan) Grant-in-Aid for Scientific Research and the Suntory Institute of Bioorganic Research. Fellowships to G.H. and M.M.S. from the Japanese Society for the Promotion of Science are gratefully acknowledged. This research was also partially supported by the Ministry of Education, Science, Sports and Culture, a Grant-in-Aid for the COE project, Giant Molecules and Complex Systems, 2002.
Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2004/5/17
Y1 - 2004/5/17
N2 - 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.
AB - 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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U2 - 10.1016/j.bmcl.2004.02.064
DO - 10.1016/j.bmcl.2004.02.064
M3 - Article
C2 - 15109670
AN - SCOPUS:1942502398
VL - 14
SP - 2647
EP - 2651
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 10
ER -
