Symmetrical α-bromoacryloylamido diaryldienone derivatives as a novel series of antiproliferative agents. Design, synthesis and biological evaluation

In a continuing study of hybrid compounds containing the α-bromoacryloyl moiety as potential anticancer drugs, we synthesized a novel series of hybrids 4a– h, in which this moiety was linked to a 1,5-diaryl-1,4-pentadien-3-one system. Many of the conjugates prepared ( 4b, 4c, 4e and 4g) demonstrated...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2010-05, Vol.20 (9), p.2733-2739
Main Authors: Romagnoli, Romeo, Baraldi, Pier Giovanni, Cruz-Lopez, Olga, Cara, Carlota Lopez, Carrion, Maria Dora, Balzarini, Jan, Hamel, Ernest, Basso, Giuseppe, Bortolozzi, Roberta, Viola, Giampietro
Format: Article
Language:English
Subjects:
Animals
Antineoplastic agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antiproliferative activity
Antitumor agents
Apoptosis
Biological and medical sciences
Caspase 3 - metabolism
Cell Line, Tumor
Chalcones - chemistry
Drug Design
Drug Evaluation, Preclinical
Drug Screening Assays, Antitumor
General aspects
HeLa Cells
Humans
Hybrid compounds
Medical sciences
Mice
Pharmacology. Drug treatments
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Summary:In a continuing study of hybrid compounds containing the α-bromoacryloyl moiety as potential anticancer drugs, we synthesized a novel series of hybrids 4a– h, in which this moiety was linked to a 1,5-diaryl-1,4-pentadien-3-one system. Many of the conjugates prepared ( 4b, 4c, 4e and 4g) demonstrated pronounced, submicromolar antiproliferative activity against four cancer cell lines. Moreover, compound 4b induced apoptosis through the mitochondrial pathway and activated caspase-3 in a concentration-dependent manner.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2010.03.075