Publication details
Synthesis of carbocyclic analogs of dehydroaltenusin: identification of a stable inhibitor of calf DNA polymerase a
| Authors | |
|---|---|
| Year of publication | 2015 |
| Type | Article in Periodical |
| Magazine / Source | Tetrahedron |
| MU Faculty or unit | |
| Citation | |
| Doi | http://dx.doi.org/10.1016/j.tet.2015.08.005 |
| Field | Organic chemistry |
| Keywords | Dehydroaltenusin; DNA polymerase; DNA damage repair; Spirocyclic compounds; Regioselective aldol condensation |
| Description | 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 (4,5-dihydroxy-6-methoxy-2-methylspiro[cyclohexa[2,5]diene-1,1-indene]-3,4(2H)-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. |