Synthesis and preliminary biological evaluation of truncated zoanthenol analogues
| Autor: | Masahiko Hayashi, Go Hirai, Koji Koyama, Masahiro Hirama, Yuuki Koizumi, Sameh M. Moharram, Hiroki Oguri |
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| Rok vydání: | 2004 |
| Předmět: |
Stereochemistry
Clinical Biochemistry Pharmaceutical Science Biochemistry Chemical synthesis Cnidaria Mice Structure-Activity Relationship chemistry.chemical_compound Alkaloids Drug Discovery Animals Structure–activity relationship Molecular Biology Cell Proliferation Biological evaluation chemistry.chemical_classification Hybridomas Dose-Response Relationship Drug Interleukin-6 Zoanthenol Molecular Mimicry Organic Chemistry General Medicine Heterocyclic Compounds Bridged-Ring chemistry Drug Design Hemiaminal Osteoporosis Molecular Medicine Pharmacophore Lactone |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 14:2647-2651 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/j.bmcl.2004.02.064 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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