Identification of the first enantiopure Rac1–Tiam1 protein–protein interaction inhibitor and its optimized synthesis via phosphine free remote group directed hydroarylation
Articolo
Data di Pubblicazione:
2019
Citazione:
Identification of the first enantiopure Rac1–Tiam1 protein–protein interaction inhibitor and its optimized synthesis via phosphine free remote group directed hydroarylation / A. Ruffoni, N. Ferri, A. Pinto, S. Pellegrino, A. Contini, F. Clerici. - In: MEDCHEMCOMM. - ISSN 2040-2503. - 10:2(2019 Feb), pp. 310-314. [10.1039/C8MD00477C]
Abstract:
A phospine free hydroarylation reaction applied to norbornene derivatives is described for the first time and was exploited for the regioselective gram scale synthesis of AR-148, a known Rac1–Tiam1 PPI inhibitor. Umpolung conversion of the nitro group into free amine allowed the regiocontrol of the key arylation step via a long range effect. The effect of AR-148 in comparison with its enantiomers on Rac1 activation of has been evaluated and (−)AR-148 has been identified as the first enantiomerically pure inhibitor of Rac1–Tiam1 PPI.
Tipologia IRIS:
01 - Articolo su periodico
Elenco autori:
A. Ruffoni, N. Ferri, A. Pinto, S. Pellegrino, A. Contini, F. Clerici
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