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Design, synthesis and biological evaluation of 3,5-disubstituted 2-amino thiophene derivatives as a novel class of antitumor agents. 2014
Romeo Romagnoli, and
Pier Giovanni Baraldi, and
Carlota Lopez-Cara, and
Maria Kimatrai Salvador, and
Delia Preti, and
Mojgan Aghazadeh Tabrizi, and
Jan Balzarini, and
Peter Nussbaumer, and
Marcella Bassetto, and
Andrea Brancale, and
Xian-Hua Fu, and
Yang-Gao, and
Jun Li, and
Su-Zhan Zhang, and
Ernest Hamel, and
Roberta Bortolozzi, and
Giuseppe Basso, and
Giampietro Viola
Dipartimento di Scienze Farmaceutiche, Via Fossato di Mortara 17-19, Università di Ferrara, 44121 Ferrara, Italy. Electronic address: rmr@unife.it.
In search of new compounds with strong antiproliferative activity and simple molecular structure, we designed a novel series of agents based on the 2-amino-3-alkoxycarbonyl/cyano-5-arylethylthiophene scaffold. The presence of the ethyl spacer between the 2',5'-dimethoxyphenyl and the 5-position of the thiophene ring, as well as the number and location of methoxy substitutents on the phenyl ring, played a profound role in affecting the antiproliferative activity. Among the synthesized compounds, we identified the 2-amino-3-cyano-[2-(2,5-dimethoxyphenyl)ethyl] thiophene 2c as the most promising derivative against a wide panel of cancer cell lines (IC50=17-130 nM). The antiproliferative activity of this compound appears to correlate well with its ability to inhibit tubulin assembly and the binding of colchicine to tubulin. Moreover 2c, as determined by flow cytometry, strongly induced arrest in the G2/M phase of the cell cycle, and annexin-V and propidium iodide staining indicate that cell death proceeds through an apoptotic mechanism that follows the intrinsic mitochondrial pathway.
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