33290-15-2Relevant academic research and scientific papers
Synthesis, structure-activity relationships and molecular modeling studies of new indole inhibitors of monoamine oxidases A and B
La Regina, Giuseppe,Silvestri, Romano,Gatti, Valerio,Lavecchia, Antonio,Novellino, Ettore,Befani, Olivia,Turini, Paola,Agostinelli, Enzo
experimental part, p. 9729 - 9740 (2009/04/06)
New monoamine oxidase inhibitors were synthesized as indole analogues of a previously reported pyrrole series. Several compounds were potent MAO-A (12, 17, 19-22, 31, 36, and 37) or MAO-B (14, 20, 24, 38, 44, and 46) inhibitors, and had Ki values in the nanomolar concentration range. In particular, 22 (Ki = 0.00092 μM, and SI = 68,478) was exceptionally potent and selective as MAO-A inhibitor. In molecular modeling studies, compounds 22, 24, 44, and 46 positioned the indole ring into an aromatic cavity of MAO-A, and established π-π stacking interactions with Tyr407, Tyr444, and FAD cofactor. However, only compound 22 was able to form hydrogen bonds with FAD, a finding which was in accordance with its potent anti-MAO-A activity. Conversely, 22/MAOB complex was highly unstable during the MD simulation.
Diastereoselective carbozincation of propargylic amines
Rezaei, Hadi,Marek, Ilan,Normant, Jean F
, p. 2477 - 2483 (2007/10/03)
The carbometalation of propargylic amines derived from methylbenzylamine takes place with good 1,3-diastereoselection in the presence of Lewis acids.
