Klein, Michael and Zabel, Manfred and Bernhardt, Günther and Koenig, Burkhard (2003) Tetrahydroxy 10-membered cyclic enediynes. JOURNAL OF ORGANIC CHEMISTRY, 68 (24). pp. 9379-9383. ISSN 0022-3263, 1520-6904
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The preparation of cyclic 10-membered tetrahydroxy enediynes is reported. The synthesis starts from tartaric acid and allows the control of the relative stereochemistry. Acetal protection of the 2,3-hydroxy groups stabilizes the enediyne during synthesis. Removal of the cyclic protecting group with EtSH/TFA transforms the stable compounds into reactive enediynes, and the rate constants of their cyclization were determined in benzene and water. The cytoxicity of the activated compounds was assayed against tumor cells in vitro, but the growth inhibitory effect was weak compared to cisplatin.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | BERGMAN CYCLIZATION; CHEMICAL-SYNTHESIS; ANTITUMOR-ACTIVITY; MOLECULAR DESIGN; DNA CLEAVAGE; DYNEMICIN-A; CYCLOAROMATIZATION; RING; FUNCTIONALITIES; REARRANGEMENT; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 27 Jul 2021 10:53 |
| Last Modified: | 27 Jul 2021 10:53 |
| URI: | https://pred.uni-regensburg.de/id/eprint/38395 |
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