Journal
TETRAHEDRON
Volume 137, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2023.133365
Keywords
tetralones; Allylpolyalkoxybenzenes; dihydrobenzo[ g ]indazoles; Selective demethylation; Toxicity; Sea urchin embryos
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An efficient method for converting plant allylpolyalkoxybenzenes into unsubstituted and arylsubstituted polymethoxylated aryldihydrobenzo[g]indazoles, analogues of combretastatin A4, has been developed. The resulting indazoles have different positions of OH-group due to selective demethylation of target compounds, and their structure was confirmed by X-ray analysis. Sea urchin embryo assay showed that aryldihydrobenzo[g]indazoles with an OH group and 1-unsubstituted pyrazole ring had systemic toxicity but lacked tubulin-related antimitotic activity. (c) 2023 Elsevier Ltd. All rights reserved.
An efficient method for the conversion of available plant allylpolyalkoxybenzenes into unsubstituted and arylsubstituted polymethoxylated aryldihydrobenzo[g]indazoles, analogues of combretastatin A4, has been developed. The selective demethylation of target compounds resulted in indazoles with different position of OH-group. Their structure was confirmed by X-ray analysis. A sea urchin embryo assay revealed the lack of tubulin-related antimitotic activity of aryldihydrobenzo[g]indazoles with systemic toxicity of a compound featuring OH group and 1-unsubstituted pyrazole ring.(c) 2023 Elsevier Ltd. All rights reserved.
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