139018-14-7Relevant articles and documents
Indole-based allosteric inhibitors of HIV-1 integrase
Patel, Pratiq A.,Kvaratskhelia, Nina,Mansour, Yara,Antwi, Janet,Feng, Lei,Koneru, Pratibha,Kobe, Mathew J.,Jena, Nivedita,Shi, Guqin,Mohamed, Mosaad S.,Li, Chenglong,Kessl, Jacques J.,Fuchs, James R.
, p. 4748 - 4752 (2016)
Employing a scaffold hopping approach, a series of allosteric HIV-1 integrase (IN) inhibitors (ALLINIs) have been synthesized based on an indole scaffold. These compounds incorporate the key elements utilized in quinoline-based ALLINIs for binding to the IN dimer interface at the principal LEDGF/p75 binding pocket. The most potent of these compounds displayed good activity in the LEDGF/p75 dependent integration assay (IC50?=?4.5?μM) and, as predicted based on the geometry of the five- versus six-membered ring, retained activity against the A128T IN mutant that confers resistance to many quinoline-based ALLINIs.
Synthetic Studies toward 1,2,3,3a,4,8b-Hexahydropyrrolo[3,2-b]indole Core. Unusual Fragmentation with 1,2-Aryl Shift
Aksenov, Alexander V.,Aksenov, Dmitrii A.,Aksenov, Nicolai A.,Aksenova, Anna A.,Aleksandrova, Elena V.,Nobi, Mezvah A.,Rubin, Michael
, p. 1434 - 1444 (2022/01/27)
Base-assisted transformations of 2-(3-oxoindolin-2-yl)acetonitriles were investigated. Unexpectedly, attempted reactions of substrates possessing nonprotected nitrogen atoms were accompanied by unusual extrusions of 2-arylacetonitriles, followed by a 1,2-aryl shift to afford 3-hydroxyindolin-2-ones. On the other hand, the reactions for N-alkyl derivatives of oxoindolines took the expected route by only providing 1,2,3,3a,4,8b-hexahydropyrrolo[3,2-b]indoles.
Electrochemical Umpolung C-H Functionalization of Oxindoles
Maulide, Nuno,Pastor, Miryam,Vayer, Marie,Weinstabl, Harald
supporting information, (2022/01/12)
Herein, we present a general electrochemical method to access unsymmetrical 3,3-disubstituted oxindoles by direct C-H functionalization where the oxindole fragment behaves as an electrophile. This Umpolung approach does not rely on stoichiometric oxidants and proceeds under mild, environmentally benign conditions. Importantly, it enables the functionalization of these scaffolds through C-O, and by extension to C-C or even C-N bond formation.