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 | |
| Publication status | Published - May 17 2004 |
| Externally published | Yes |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Molecular Medicine
- Molecular Biology
- Pharmaceutical Science
- Drug Discovery
- Clinical Biochemistry
- Organic Chemistry
Cite this
Synthesis and preliminary biological evaluation of truncated zoanthenol analogues. / Hirai, Go; Oguri, Hiroki; Hayashi, Masahiko; Koyama, Koji; Koizumi, Yuuki; Moharram, Sameh M.; Hirama, Masahiro.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 14, No. 10, 17.05.2004, p. 2647-2651.Research output: Contribution to journal › Article
}
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
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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UR - http://www.scopus.com/inward/citedby.url?scp=1942502398&partnerID=8YFLogxK
U2 - 10.1016/j.bmcl.2004.02.064
DO - 10.1016/j.bmcl.2004.02.064
M3 - Article
VL - 14
SP - 2647
EP - 2651
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 10
ER -