Synthesis of carbocyclic analogs of dehydroaltenusin: identification of a stable inhibitor of calf DNA polymerase a

KOVÁČOVÁ, Silvia, Santosh Kumar ADLA, Lukáš MAIER, Michal BABIAK, Yoshiyuki MIZUSHINA and Kamil PARUCH. Synthesis of carbocyclic analogs of dehydroaltenusin: identification of a stable inhibitor of calf DNA polymerase a. Tetrahedron. Pergamon Press, 2015, vol. 71, No 40, p. 7575-7582. ISSN 0040-4020. Available from: https://dx.doi.org/10.1016/j.tet.2015.08.005.

Basic information

• Original name: Synthesis of carbocyclic analogs of dehydroaltenusin: identification of a stable inhibitor of calf DNA polymerase a
• Authors: KOVÁČOVÁ, Silvia (703 Slovakia, belonging to the institution), Santosh Kumar ADLA (356 India, belonging to the institution), Lukáš MAIER (203 Czech Republic, belonging to the institution), Michal BABIAK (703 Slovakia, belonging to the institution), Yoshiyuki MIZUSHINA (392 Japan) and Kamil PARUCH (203 Czech Republic, belonging to the institution).
• Edition: Tetrahedron, Pergamon Press, 2015, 0040-4020.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10401 Organic chemistry
• Country of publisher: United Kingdom of Great Britain and Northern Ireland
• Confidentiality degree: is not subject to a state or trade secret
• Impact factor: Impact factor: 2.645
• RIV identification code: RIV/00216224:14310/15:00083970
• Organization unit: Faculty of Science
• Doi: http://dx.doi.org/10.1016/j.tet.2015.08.005
• UT WoS: 000361161500007
• Keywords in English: Dehydroaltenusin; DNA polymerase; DNA damage repair; Spirocyclic compounds; Regioselective aldol condensation
• Tags: AKR, rivok

Abstract

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.