Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 9, Issue -, Pages 2328-2335Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.9.267
Keywords
cyclopamine; hedgehog signaling pathway; natural products; steroidal alkaloids; structure-activity relationship
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The chemical synthesis and biological evaluation of new cyclopamine analogs bearing exocyclic methylenes in different positions is described. Bis-exo- cyclopamine 6 was identified as a potent inhibitor of the Gli1-dependent luciferase expression in Shh-LIGHTII cells. An extension of this study to F- ring-modified structures shows the necessity of a rigidly positioned nitrogen atom for bioactivity as well as the presence of the C21 methyl group for acid stability and bioactivity.
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