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Thiazolo[5,4‐ f ]quinoxalines, Oxazolo[5,4‐ f ]quinoxalines and Pyrazino[ b,e ]isatins: Synthesis from 6‐Aminoquinoxalines and Properties
Author(s) -
Lassagne Frédéric,
Sims Joshua M.,
Erb William,
Mongin Olivier,
Richy Nicolas,
El Osmani Nour,
Fajloun Ziad,
Picot Laurent,
Thiéry Valérie,
Robert Thomas,
Bach Stéphane,
Dorcet Vincent,
Roisnel Thierry,
Mongin Florence
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100362
Subject(s) - regioselectivity , quinoxaline , chemistry , sonogashira coupling , ring (chemistry) , stereochemistry , combinatorial chemistry , azole , catalysis , organic chemistry , antifungal , medicine , palladium , dermatology
The regioselective iodination of different 2‐mono‐, 3‐mono‐ and 2,3‐disubstituted 6‐aminoquinoxalines, which takes place at their 5‐position, was rationalized on the basis of Hückel theory calculations. Oxazolo‐ and thiazolo[5,4‐ f ]quinoxaline analogues of reported disease‐related protein kinases inhibitors were synthesized from the obtained 6‐amino‐5‐iodoquinoxalines by using as key step copper‐catalyzed azole ring formation. Pyrazino[ b,e ]isatins were obtained, for the first time, from the same substrates by recourse to Sonogashira coupling, alkyne hydration, and oxidative cyclization. The absorption and emission properties of the most promising compounds were recorded. In addition, most of the synthesized polycycles were evaluated as protein kinase inhibitors and for their antiproliferative activity towards cancer cells.