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Enantioselective Total Syntheses of the Proposed Structures of Prevezol B and Evaluation of Anti-Cancer Activity

Leung, Anna E; Rubbiani, Riccardo; Gasser, Gilles; Tuck, Kellie L (2014). Enantioselective Total Syntheses of the Proposed Structures of Prevezol B and Evaluation of Anti-Cancer Activity. Organic & Biomolecular Chemistry, 12:8239-8246.

Abstract

The first enantioselective total syntheses of the proposed structures of the natural product prevezol B are reported. The reported syntheses complement the previously-reported syntheses of the proposed structures of prevezol C, a stereoisomer of prevezol B. It was previously shown that the structure of the naturally occurring prevezol C had been incorrectly assigned. This work has led us to conclude that the proposed structures of prevezol B are also incorrect and major revision of both of the structures of the prevezols B and C is required. Cytotoxicity studies on the human cervical cancer cell line HeLa revealed that the synthesized prevezol B and C compounds were not active even at the highest concentration used (100 μM). However, one of the synthetic precursors was shown to have modest potency against HeLa cells (IC50 = 23.5 ± 1.8 μM).

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Life Sciences > Biochemistry
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Language:English
Date:2014
Deposited On:06 Nov 2014 12:28
Last Modified:11 Jun 2025 01:39
Publisher:RSC Publishing
ISSN:1477-0520
OA Status:Closed
Publisher DOI:https://doi.org/10.1039/c4ob01662a
PubMed ID:25199510

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