Universität zu Köln

Yadav, Dharmendra B., Taleli, Lebusetsa, van der Westhuyzen, Alet E., Fernandes, Manuel A., Dragoun, Maxim, Prokop, Aram, Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827, de Koning, Charles B. and van Otterlo, Willem A. L. (2015). Synthesis of Diverse 6-Oxa-allocolchicinoids by a Suzuki-Miyaura Coupling, Acid-Catalyzed Intramolecular Transacetalization Strategy. Eur. J. Org. Chem., 2015 (23). S. 5167 - 5183. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1099-0690

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Abstract

The synthesis of allocolchicine analogues is of importance as these compounds have been found to possess promising anticancer activity by affecting tubulin polymerization. In this paper, the synthesis of 28 novel substituted 6-oxa-allocolchicinoids is reported. The key steps involved in the synthesis were a Suzuki-Miyaura coupling reaction, followed by an acid-catalyzed intramolecular transacetalization to afford the desired 5-alkoxy-5,7-dihydrodibenzo[c,e]oxepines. In addition, when thiophenol and phenol were used in the transacetalization step, the 5-(phenylsulfanyl)-5,7-dihydrodibenzo[c,e]oxepine and 4-(5,7-dihydrodibenzo[c,e]oxepin-5-yl)phenol skeletons were obtained, respectively. The cytotoxicity of the synthetic compounds was unfortunately not impressive; however, one of the compounds was shown to sensitize vincristine-resistant leukemia and lymphoma cells to vincristine, a result vindicating further synthetic studies.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Yadav, Dharmendra B. UNSPECIFIED UNSPECIFIED UNSPECIFIED Taleli, Lebusetsa UNSPECIFIED UNSPECIFIED UNSPECIFIED van der Westhuyzen, Alet E. UNSPECIFIED UNSPECIFIED UNSPECIFIED Fernandes, Manuel A. UNSPECIFIED UNSPECIFIED UNSPECIFIED Dragoun, Maxim UNSPECIFIED UNSPECIFIED UNSPECIFIED Prokop, Aram UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED de Koning, Charles B. UNSPECIFIED UNSPECIFIED UNSPECIFIED van Otterlo, Willem A. L. UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-398058
DOI:	10.1002/ejoc.201500573
Journal or Publication Title:	Eur. J. Org. Chem.
Volume:	2015
Number:	23
Page Range:	S. 5167 - 5183
Date:	2015
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1099-0690
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language ASYMMETRIC-SYNTHESIS; ALLOCOLCHICINE ANALOGS; ANTITUMOR AGENTS; RING; TUBULIN; DERIVATIVES; COLCHICINOIDS; CYCLIZATION; INHIBITION; BINDING Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/39805