108791-78-2Relevant articles and documents
Synthesis of diverse lactam carboxamides leading to the discovery of a new transcription-factor inhibitor
Ng, Pui Yee,Tang, Yuchen,Knosp, Wendy M.,Stadler, H. Scott,Shaw, Jared T.
, p. 5352 - 5355 (2007)
(Chemical Equation Presented) Diversity is the key: Skeletal diversity is a useful starting point in the search for compounds that modulate protein-biopolymer interactions. A library of 400 lactam carboxamides has been synthesized in a short synthetic sequence and a new compound that inhibits the interaction of a transcription factor (HOXA13) with its DNA target has been discovered, and inhibition of transcription is demonstrated in cells.
Synthesis of polyheterocyclic pyrrolo[3,4-b]pyridin-5-ones via a one-pot (Ugi-3CR/aza diels-alder/N-acylation/aromatization/SN2) process. A suitable alternative towards novel Aza-analogues of falipamil
Zamudio-Medina, Angel,García-González, Ailyn N.,Herrera-Carrillo, Genesis K.,Zárate-Zárate, Daniel,Benavides-Macías, Adriana,Tamariz, Joaquín,Ibarra, Ilich A.,Islas-Jácome, Alejandro,González-Zamora, Eduardo
, (2018/04/06)
We describe the one-pot synthesis of twenty polyheterocyclic pyrrolo[3,4-b]pyridin-5-ones via a cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization) in 20 to 95% overall yields, as well as four pharmacologically promising analogues via an improved cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2): two piperazine-linked pyrrolo[3,4b]pyridin-5-ones in 33 and 34%, and a couple of Falipamil aza-analogues in 30 and 35% overall yields. It is worth highlighting the good substrate scope found, because final products are furnished with alkyl, aryl, and heterocyclic substituents. The use of chain-ring tautomerizable isocyanides (as key reagents for the Ugi-type three component reaction) allowed for a rapid and efficient assembly of the polysubstituted oxindoles, which were used in situ toward the complex products, conferring features like robustness, sustainability, and the one-pot approach to this synthetic methodology.
Ugi four-component reaction of alcohols: Stoichiometric and catalytic oxidation/MCR sequences
Drouet, Fleur,Masson, Géraldine,Zhu, Jieping
, p. 2854 - 2857 (2013/07/26)
A new, simple, and efficient procedure for the one-pot Ugi four-component reaction of alcohols instead of aldehydes is described. Using a stoichiometric amount of IBX or only 1-2% of sodium 2-iodobenzenesulfonate in the presence of Oxone, a wide range of primary alcohols were oxidized to the aldehyde that were directly engaged in the Ugi four-component reaction to afford α-acetamidoamides in good to excellent yields.