77960-29-3Relevant articles and documents
Integrated Synthetic, Biophysical, and Computational Investigations of Covalent Inhibitors of Prolyl Oligopeptidase and Fibroblast Activation Protein α
Plescia, Jessica,De Cesco, Stéphane,Patrascu, Mihai Burai,Kurian, Jerry,Di Trani, Justin,Dufresne, Caroline,Wahba, Alexander S.,Janmamode, Na?la,Mittermaier, Anthony K.,Moitessier, Nicolas
, p. 7874 - 7884 (2019/10/11)
Over the past decade, there has been increasing interest in covalent inhibition as a drug design strategy. Our own interest in the development of prolyl oligopeptidase (POP) and fibroblast activation protein α (FAP) covalent inhibitors has led us to question whether these two serine proteases were equal in terms of their reactivity toward electrophilic warheads. To streamline such investigations, we exploited both computational and experimental methods to investigate the influence of different reactive groups on both potency and binding kinetics using both our own series of POP inhibitors and others' discovered hits. A direct correlation between inhibitor reactivity and residence time was demonstrated through quantum mechanics methods and further supported by experimental studies. This computational method was also successfully applied to FAP, as an overview of known FAP inhibitors confirmed our computational predictions that more reactive warheads (e.g., boronic acids) must be employed to inhibit FAP than for POP.
Cycloaddition of furfurylamines to maleic anhydride and its substituted derivatives
Zaytsev,Mikhailova,Airiyan,Galkina,Golubev,Nikitina,Zubkov,Varlamov
, p. 505 - 513 (2012/10/29)
The regio- and stereoselectivity of the [4+2] cycloaddition of maleic, citraconic, dichloromaleic, and dibromomaleic anhydrides to difurfuryl amines and secondary furfurylamines were studied. N-Furfuryl-, N-phenyl-, and N-benzylhexahydrooxoepoxyisoindole-7-carboxylic acids were synthesized. An approach was developed for obtaining hexahydroepoxyoxoisoindole-7-carboxylic acid unsubstituted at the nitrogen atom. Aromatization of the oxabicycloheptene fragment of the dihaloepoxyiso-indolonecarboxylic acids gave a series of 7-carboxy-2-R-isoindol-1-ones.
A facile, protic ionic liquid route to N-substituted 5-hydroxy-4-methyl-3- oxoisoindoline-1-carboxamides and N-substituted 3-oxoisoindoline-4-carboxylic acids
Gordon, Christopher P,Byrne, Nolene,McCluskey, Adam
experimental part, p. 1000 - 1006 (2010/10/18)
Treatment of highly decorated bicyclo[2.2.1]heptadienes with the protic ionic liquid, TfOH:TEA effected quantitative conversion to the corresponding N-substituted 5-hydroxy-4-methyl-3-oxoisoindoline-1-carboxamides. This approach provides rapid access important chemical space for the rapid development of highly functionalised oxoisoindoline and is highly substrate tolerant.
