843652-40-4Relevant articles and documents
A new four-component reaction involving the Michael addition and the Gewald reaction, leading to diverse biologically active 2-aminothiophenes
Thomas, Joice,Jana, Sampad,Sonawane, Mahendra,Fiey, Bert,Balzarini, Jan,Liekens, Sandra,Dehaen, Wim
, p. 3892 - 3900 (2017)
The Gewald three-component reaction yielding highly substituted 2-aminothiophene heterocycles has been known for a long time and holds an extraordinary potential in the pharmaceutical industry. Herein, we describe a four-component reaction initiated by the conjugate addition of different indole derivatives to α,β-unsaturated carbonyl compounds. This is followed by an in situ Gewald three-component reaction which results in the formation of a compound containing an indole and a 2-aminothiophene moiety separated by a methylene spacer. We also examined the impact of the use of other nucleophilic components such as pyrrole derivatives on this MG-4CR (Michael-Gewald four component reaction). All these synthesized compounds were tested for anti-proliferative activity and three of them showed activity in the nanomolar range.
Palladium-Mediated Oxidative Annulation of δ-Indolyl-α,β-Unsaturated Compounds toward the Synthesis of Cyclopenta[ b]indoles and Heterogeneous Hydrogenation to Access Fused Indolines
Agy, André Capretz,Rodrigues, Manoel T.,Zeoly, Lucas A.,Simoni, Deborah A.,Coelho, Fernando
, p. 5564 - 5581 (2019/05/06)
The cyclopenta[b]indole moiety represents a key skeletal unit in several natural and synthetic compounds that exhibit diverse biological properties. We described herein a two-step sequence for synthesizing cyclopenta[b]indoles with great structural diversity in overall yields up to 37%. The key step was a palladium-catalyzed oxidative annulation of 3-alkylindoles (Fujiwara-Moritani reaction). The obtained cyclopenta[b]indoles were used as substrates in heterogeneous hydrogenation reactions to afford new fused indolines in moderate yields. An acid-catalyzed intramolecular cyclization of three such indolines gave tetracyclic lactams in 89, 90, and 61% yields.
Advances toward new antidepressants with dual serotonin transporter and 5-HT1A receptor affinity within a class of 3-aminochroman derivatives. Part 2
Hatzenbuhler, Nicole T.,Baudy, Reinhardt,Evrard, Deborah A.,Failli, Amedeo,Harrison, Boyd L.,Lenicek, Steven,Mewshaw, Richard E.,Saab, Annmarie,Shah, Uresh,Sze, Jean,Zhang, Minsheng,Zhou, Dahui,Chlenov, Michael,Kagan, Michael,Golembieski, Jeannette,Hornby, Geoffrey,Lai, Margaret,Smith, Deborah L.,Sullivan, Kelly M.,Schechter, Lee E.,Andree, Terrance H.
supporting information; experimental part, p. 6980 - 7004 (2009/11/30)
Novel compounds combining a 5-HT1A moiety (3-aminochroman scaffold) and a 5-HT transporter (indole analogues) linked through a common basic nitrogen via an alkyl chain attached at the 1- or 3-position of the indole were evaluated for dual affin
