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.
Synthesis, structure-activity relationships and stereochemical investigations on new tricyclic pyridazinone derivatives as potential STAT3 inhibitors / F. Meneghetti, D. Masciocchi, A. Gelain, F. Porta, A. Pedretti, G. Celentano, D. Barlocco, L. Legnani, L. Toma, B. Kwon, A. Asai, S. Villa. ((Intervento presentato al 7. convegno Nuove Prospettive in Chimica Farmaceutica tenutosi a Savigliano nel 2013.
Synthesis, structure-activity relationships and stereochemical investigations on new tricyclic pyridazinone derivatives as potential STAT3 inhibitors
F. Meneghetti;D. Masciocchi;A. Gelain;F. Porta;A. Pedretti;G. Celentano;D. Barlocco;S. Villa
2013
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.File | Dimensione | Formato | |
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