Homoarcyriaflavin: Synthesis of ring-expanded arcyriaflavin analogues

Mahboobi, Siavosh and Burgemeister, Thomas and Dove, Stefan and Kuhr, Sabine and Popp, Alfred (1999) Homoarcyriaflavin: Synthesis of ring-expanded arcyriaflavin analogues. JOURNAL OF ORGANIC CHEMISTRY, 64 (22). pp. 8130-8137. ISSN 0022-3263,

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Abstract

The construction of the ring-expanded carbazole system, forming arcyriaflavin homologues, is efficiently accomplished by the reaction of 2,2'-bridged bis-indoles with 3,4-dibromo-2,5-dihydro-1H-2,5-pyrroledione derivatives under Grignard conditions A ring size of up to nine members in the central ring is achievable. Substitutions either at the indole system or at the imide-N are also possible. The conformation of homoarcyriaflavins as a cross-link between the rigid arcyriaflavins and the flexible arcyriarubins was investigated by NMR, X-ray, and semiempiric quantum chemical calculation methods.

Item Type: Article
Uncontrolled Keywords: PROTEIN-KINASE-C; INHIBITORS; REBECCAMYCIN; POTENT; INDOLOCARBAZOLE; STAUROSPORINE;
Subjects: 600 Technology > 615 Pharmacy
Divisions: Chemistry and Pharmacy > Institute of Pharmacy > Pharmaceutical/Medicinal Chemistry I (Prof. Elz)
Depositing User: Dr. Gernot Deinzer
Date Deposited: 13 Dec 2022 13:03
Last Modified: 13 Dec 2022 13:03
URI: https://pred.uni-regensburg.de/id/eprint/48911

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