Document Detail


Design, synthesis and antiproliferative activity of styryl lactones related to (+)-goniofufurone.
MedLine Citation:
PMID:  20359789     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
This paper describes a straightforward divergent synthesis of (+)-goniofufurone mimics (4, 5 and 6) starting from d-xylose. In a preliminary bioassay, analogues 4 and 5 exhibited a submicromolar antiproliferative activity towards HL-60 cells, while the corresponding parent compound 1 was completely inactive against this cell line. At the same time, these molecules showed approximately 10-fold stronger cytotoxicity in the same cell line when compared to the standard anticancer drug doxorubicin (DOX). Analogue 6 displayed 18- and 3-fold higher potency in Raji cell line when compared to control compounds 1 and DOX, respectively. A new divergent route for the preparation of (+)-goniofufurone (1) and (+)-crassalactone C (3) from d-xylose is also disclosed.
Authors:
Velimir Popsavin; Bojana Srećo; Goran Benedeković; Jovana Francuz; Mirjana Popsavin; Vesna Kojić; Gordana Bogdanović
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2010-03-12
Journal Detail:
Title:  European journal of medicinal chemistry     Volume:  45     ISSN:  1768-3254     ISO Abbreviation:  Eur J Med Chem     Publication Date:  2010 Jul 
Date Detail:
Created Date:  2010-05-17     Completed Date:  2010-08-17     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0420510     Medline TA:  Eur J Med Chem     Country:  France    
Other Details:
Languages:  eng     Pagination:  2876-83     Citation Subset:  IM    
Copyright Information:
Copyright (c) 2010 Elsevier Masson SAS. All rights reserved.
Affiliation:
Department of Chemistry, Faculty of Sciences, University of Novi Sad, Trg D. Obradovića 3, 21000 Novi Sad, Serbia. velimir.popsavin@dh.uns.ac.rs
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MeSH Terms
Descriptor/Qualifier:
Antineoplastic Agents / chemical synthesis,  chemistry*,  pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Drug Design*
Humans
Hydrophobicity
Inhibitory Concentration 50
Lactones / chemical synthesis,  chemistry*,  pharmacology*
Stereoisomerism
Chemical
Reg. No./Substance:
0/Antineoplastic Agents; 0/Lactones; 136778-39-7/7-goniofufurone

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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