Studies on quinones. Part 42: Synthesis of furylquinone and hydroquinones with antiproliferative activity against human tumor cell lines

• Type: Article in International Scientific Journal
• Date: 2008

Authors

Julio Benites (Author) Other; Jaime A Valderrama (Author) Other; Felipe Rivera (Author) Other; Leonel Rojo (Author) Other; Nair Campos (Author) Other; Madalena Pedro (Author) Other; Maria Saeo J Jose Nascimento (Author) FFUP

Journal

Title: Bioorganic and Medicinal Chemistry

Vol. 16

Pages: 862-868

ISSN: 0968-0896

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 26 Citations

Scopus - 22 Citations

Pubmed / Medline

Scientific classification

FOS: Natural sciences > Chemical sciences

CORDIS: Health sciences

Other information

Authenticus ID: P-004-21F

DOI: 10.1016/j.bmc.2007.10.028

Resumo (PT): The preparation of furyl-1,4-quinone and hydroquinones by reaction of 2-furaldehyde N,N-dimethylhydrazone with benzo- and naphthoquinones is reported. Access to furylnaphthoquinones from unactivated quinones requires acid-induced conditions, however oxidative coupling reactions of activated quinones proceed under neutral conditions. The in vitro cytotoxic activity of the prepared compounds against a panel of three human cancer cell lines has been studied. Most of the furyl-1,4-quinones exhibited good antiproliferative activity (GI50 = 6.5–33.5 μm) against the MCF-7, NCI-H460, and SF-268 (CNS cancer) cell lines chosen for testing. <br> <br> Keywords: Quinones; Michael addition; Oxidative coupling; Cytotoxicity <br> <a target="_blank" href="http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TF8-4PWKSJP-B&_user=2460038&_coverDate=01%2F15%2F2008&_rdoc=28&_fmt=high&_orig=browse&_origin=browse&_zone=rslt_list_item&_srch=doc-info(%23toc%235220%232008%23999839997%23679185%23FLA%23display%23Volume)&_cdi=5220&_sort=d&_docanchor=&_ct=46&_acct=C000057398&_version=1&_urlVersion=0&_userid=2460038&md5=2a62b0882e4eb8525be6bc1d921a004a&searchtype=a "> Texto integral </a> <br> <br>

Abstract (EN): The preparation of furyl-1,4-quinone and hydroquinones by reaction of 2-furaldehyde N,N-dimethylhydrazone with benzo- and naphthoquinones is reported. Access to furylnaphthoquinones from unactivated quinones requires acid-induced conditions, however oxidative coupling reactions of activated quinones proceed under neutral conditions. The in vitro cytotoxic activity of the prepared compounds against a panel of three human cancer cell lines has been studied. Most of the furyl-1,4-quinones exhibited good antiproliferative activity (GI(50) = 6.5-33.5 mu m) against the MCF-7, NCI-H460, and SF-268 (CNS cancer) cell lines chosen for testing.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 7