Synthesis of cytotoxic fluorinated quassinoids

The C-15 senecioyl side chain of brusatol was interchanged with fluorinated acyl groups, and the C-3 hydroxy group of bruceolide was esterified with fluorinated acyl chlorides. These fluorinated quassinoids 11, 12, 13, and 17 showed significant cytotoxic activity against eight human cancer cell line...

Full description

Saved in:
Bibliographic Details
Published in:Bioorganic & medicinal chemistry 1997-08, Vol.5 (8), p.1489-1495
Main Authors: Ohno, Nobuhiro, Fukamiya, Narihiko, Okano, Masayoshi, Tagahara, Kiyoshi, Lee, Kuo-Hsiung
Format: Article
Language:English
Subjects:
Acylation
Antineoplastic Agents, Phytogenic - chemical synthesis
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - pharmacology
Fluorine
Glaucarubin - analogs & derivatives
Glaucarubin - chemical synthesis
Glaucarubin - chemistry
Glaucarubin - pharmacology
Humans
Models, Chemical
Quassins
Tumor Cells, Cultured - drug effects
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The C-15 senecioyl side chain of brusatol was interchanged with fluorinated acyl groups, and the C-3 hydroxy group of bruceolide was esterified with fluorinated acyl chlorides. These fluorinated quassinoids 11, 12, 13, and 17 showed significant cytotoxic activity against eight human cancer cell lines including small and non-small cell lung, colon, CNS, ovarian and renal cancers, leukemia, and melanoma with 17 being about 100 times more potent than 11, 12, and 13. The activity of 17 was similar to that of bruceantin ( 1) in this in vitro cell line panel. Synthesis and in vitro antineoplastic activity of four fluorinated quassinoid derivatives ( 11– 13, and 17).
ISSN:0968-0896
1464-3391
DOI:10.1016/S0968-0896(97)00095-3