A series of 2,3-heteroarylmaleimides 9 and polyheterocondensed imides 12 were prepared in good yields and short reaction time using a very efficient procedure consisting in the condensation of the corresponding anhydrides and N,N-diethylethylenediamine and microwave heating. The antiproliferative activity of the novel molecules was tested against human tumor cells (NCI-H460 lung carcinoma) and rat aortic smooth muscle cells (SMCs). The IC50 values for the novel molecules ranged from 0.08 to 13.9 lM in SMCs, and from 0.84 to 9 lM in the tumor cell line. The activity profile for compounds 9 and 12 is comparable to that obtained for amonafide in NCI-H460, except for fused imides 12b,i which proved to be about 10-fold more potent. Whereas, in rat SMCs, only the compound 12b was shown to be 10-fold more potent than amonafide. Instead 12c is equipotent to amonafide. These results suggest that the extended p-system and the kind of heteroatom are essential in the binding with the molecular target

Antiproliferative effects on human tumor cells and rat aortic smooth muscular cells of 2,3-heteroarylmaleimides and heterofused imides / N. Ferri, E.M. Beccalli, A. Contini, A. Corsini, M. Antonino, T. Radice, G. Pratesi, S. Tinelli, F. Zunino, M.L. Gelmi. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 0968-0896. - 16:4(2008), pp. 1691-1701.

Antiproliferative effects on human tumor cells and rat aortic smooth muscular cells of 2,3-heteroarylmaleimides and heterofused imides

N. Ferri;E.M. Beccalli;A. Contini;A. Corsini;M.L. Gelmi
2008

Abstract

A series of 2,3-heteroarylmaleimides 9 and polyheterocondensed imides 12 were prepared in good yields and short reaction time using a very efficient procedure consisting in the condensation of the corresponding anhydrides and N,N-diethylethylenediamine and microwave heating. The antiproliferative activity of the novel molecules was tested against human tumor cells (NCI-H460 lung carcinoma) and rat aortic smooth muscle cells (SMCs). The IC50 values for the novel molecules ranged from 0.08 to 13.9 lM in SMCs, and from 0.84 to 9 lM in the tumor cell line. The activity profile for compounds 9 and 12 is comparable to that obtained for amonafide in NCI-H460, except for fused imides 12b,i which proved to be about 10-fold more potent. Whereas, in rat SMCs, only the compound 12b was shown to be 10-fold more potent than amonafide. Instead 12c is equipotent to amonafide. These results suggest that the extended p-system and the kind of heteroatom are essential in the binding with the molecular target
2,3-heteroarylmaleimides ; heterofused imides ; synthesis ; biological activity ; antiproliferative ; human tumor cells ; rat aortic smooth muscular cells
Settore BIO/14 - Farmacologia
Settore CHIM/06 - Chimica Organica
BIOORGANIC & MEDICINAL CHEMISTRY
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/43792
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