108163-97-9Relevant articles and documents
Design, synthesis, biological evaluation and molecular modelling of substituted pyrrolo[2,1-: A] isoquinolinone derivatives: Discovery of potent inhibitors of AChE and BChE
Parravicini, Oscar,Angelina, Emilio,Spinelli, Roque,Garibotto, Francisco,Siano, álvaro S.,Vila, Laura,Cabedo, Nuria,Cortes, Diego,Enriz, Ricardo D.
, p. 8321 - 8334 (2021)
We report here the design, synthesis and biological evaluation of a new series of substituted pyrrolo[2,1-a]isoquinolin-3-one derivatives, some of which have strong inhibitory activity against both AChE and BChE enzymes. The design of these new inhibitors was carried out taking rivastigmine as the starting structure. Thus, on the basis of an exhausting molecular modeling study using combined techniques (docking, dynamic molecular simulations and QTAIM calculations), we obtained new ligands possessing stronger inhibitory effects than rivastigmine, the reference compound. QTAIM analysis gave us detailed information about the molecular interactions stabilizing the different ligand-enzyme complexes. These calculations showed the importance of the interaction with the CAS esteratic site for the inhibitory effect of these compounds. Nevertheless, they also indicated that the combination of interactions with CAS and strong interactions with the PAS site might be beneficial for the inhibitory effect.
Synthesis of new antimicrobial pyrrolo[2,1-a]isoquinolin-3-ones
Moreno, Laura,Parraga, Javier,Galan, Abraham,Cortes, Diego,Cabedo, Nuria,Primo, Jaime
, p. 6589 - 6597,9 (2012/12/12)
The attractive structure of the pyrroloisoquinoline moiety, together with its potential antimicrobial activity, encouraged us to prepare six 8-substituted and seven 8,9-disubstituted-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinolin-3- ones in a few steps with good yields. We applied a convenient methodology via double intramolecular cyclization conducted by a Bischler-Napieralski cyclodehydration-imine reduction sequence, which is widely employed in the synthesis of isoquinoline alkaloids. Therefore, we synthesized three series of these pyrrolo[2,1-a]isoquinolin-3-ones characterized by the substituent at the 8-position or 8,9-positions of the aromatic ring: (a) different side chains are attached to an 8-OH group (series 1); (b) a chlorine atom is attached to the 8-position (series 2); and (c) 8- and 9-carbons are bearing an identical group (series 3). The compounds bearing a benzylic moiety at the 8-position, for example, 8-benzyloxy-pyrrolo[2,1-a]isoquinolin-3-one (1a) and 8-(4-fluorobenzyloxy)-pyrrolo[2,1-a]isoquinolin-3-one (1e), as well as, a 8-chloro-9-methoxy moiety including the 8-chloro-9-methoxy-pyrrolo[2,1-a] isoquinolin-3-one (2a), provided the most fungicide and bactericide agents, respectively.
SYNTHESIS AND PHARMACODYNAMIC INVESTIGATION OF NEW ISOGUVACINE ANALOGUES WITH BENZOQUINOLIZINE SKELETON
Blasko, Gabor,Kardos, Julianna,Baitz-Gacs, Eszter,Simonyi, Miklos,Szantay, Csaba
, p. 2887 - 2900 (2007/10/02)
Stereoisomer hydroxy-esters 15 - 19 as well as isoguvacine analogue 20 with benzoquinolizine skeleton have been prepared via regioselective Dieckmann condensation of diester 9 followed by subsequent reduction and E2-elimination.Compounds 16 and 20 have shown a considerable in vitro activity at the GABA/benzodiazepine receptor complex.
