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Issue 8, 2013
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Synthesis, structure–activity relationships and stereochemical investigations of new tricyclic pyridazinone derivatives as potential STAT3 inhibitors

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Abstract

Through a cell-based biological screening, the benzocinnolinone derivative (±)-2c was identified as a promising STAT3 inhibitor. Since SAR studies on a series of compounds structurally related to (±)-2c (1c, 2a–p, 3c, 4c, 6) showed that the latter had the most significant inhibitory activity, we investigated in depth its essential structural features. In particular, enantiomeric separation was performed, and the absolute configuration of the stereoisomers was assigned by theoretical and crystallographic studies. The biological evaluation highlighted that (S)-(−)-2c is twice as potent as (R)-(+)-2c.

Graphical abstract: Synthesis, structure–activity relationships and stereochemical investigations of new tricyclic pyridazinone derivatives as potential STAT3 inhibitors

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Publication details

The article was received on 27 Mar 2013, accepted on 19 Jun 2013 and first published on 21 Jun 2013


Article type: Concise Article
DOI: 10.1039/C3MD00095H
Med. Chem. Commun., 2013,4, 1181-1188

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    Synthesis, structure–activity relationships and stereochemical investigations of new tricyclic pyridazinone derivatives as potential STAT3 inhibitors

    D. Masciocchi, A. Gelain, F. Porta, F. Meneghetti, A. Pedretti, G. Celentano, D. Barlocco, L. Legnani, L. Toma, B. Kwon, A. Asai and S. Villa, Med. Chem. Commun., 2013, 4, 1181
    DOI: 10.1039/C3MD00095H

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