Header

UZH-Logo

Maintenance Infos

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).

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).

Statistics

Citations

3 citations in Web of Science®
3 citations in Scopus®
Google Scholar™

Altmetrics

Downloads

1 download since deposited on 06 Nov 2014
0 downloads since 12 months
Detailed statistics

Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2014
Deposited On:06 Nov 2014 12:28
Last Modified:21 Nov 2017 17:31
Publisher:RSC Publishing
ISSN:1477-0520
Publisher DOI:https://doi.org/10.1039/c4ob01662a
PubMed ID:25199510

Download