Journal
TETRAHEDRON
Volume 71, Issue 40, Pages 7575-7582Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.08.005
Keywords
Dehydroaltenusin; DNA polymerase; DNA damage repair; Spirocyclic compounds; Regioselective aldol condensation
Categories
Funding
- SoMoPro Programme [SRGA771]
- European Community [229603]
- South Moravian Region
- Grants-in-Aid for Scientific Research [24580205] Funding Source: KAKEN
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Syntheses of carbocyclic analogs of dehydroaltenusin tautomers are reported. Both target compounds, cDHA (2,8-dihydroxy-6-methoxy-10a-methyl-10,10a-dihydrophenanthrene-3,9-dione) and cDHAs (4',5dihydroxy-6'-methoxy-2-methylspirolcyclohexa[2,5]diene-1,1'-indene]-3',4(2'H)-dione), were prepared from 3,5-dimethoxybenzaldehyde in 11 and 13 steps, respectively. Unlike dehydroaltenusin, both cDHA and cDHAs are stable and their structures were confirmed by X-ray crystallography. Compound cDHA was found to be active against calf DNA polymerase a but not related isozymes, while the spirocyclic analog cDHAs was inactive. (C) 2015 Elsevier Ltd. All rights reserved.
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