An eco-friendly acetylcholine iodide-ethylene glycol (ACI/EG) deep eutectic mixture mediated green protocol has been developed for the synthesis of hitherto unexplored multi-functionalized linear tricyclic spiropyrrolo[1,2-]isoquinoline analogues. The effects of the synthesized compounds on the osteoblast differentiation of hBMSC-TERT cell lines were investigated and promising results were observed with significant IC values. In addition, molecular modeling simulations were also performed with the 3D structure of BMP-2 to reveal binding interactions and orientations of highly potent spiropyrrolo[1,2-]isoquinoline analogues.
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http://dx.doi.org/10.1039/c8ra00646f | DOI Listing |
J Org Chem
October 2021
Institut UTINAM - UMR CNRS 6213, Université Bourgogne Franche-Comté, 16 Route de Gray, 25030 Besançon, France.
An efficient diastereoselective route is developed to get access to novel spiropyrrolo[1,2-]isoquinoline-oxindole skeletons by a -component [3 + 2] cycloaddition reaction of ()-5-arylidene-1,3-thiazolidine-2,4-diones, isatin derivatives, and 1,2,3,4-tetrahydroisoquinoline (THIQ). Interestingly, the regioselectivity of the reaction is both temperature- and solvent-dependent, allowing the synthesis of two regioisomeric -dispiropyrrolo[2,1-]isoquinolineoxindoles in excellent yield. Unprecedentedly, each isomeric dispiropyrrolo[2,1-]isoquinolineoxindole endured 1,3-dipolar cycloaddition/recycloaddition reactions under thermal or catalytic conditions to regenerate the corresponding regioisomeric counterpart.
View Article and Find Full Text PDFRSC Adv
April 2018
Department of Chemistry, College of Science, King Saud University P.O. Box 2455 Riyadh 11451 Saudi Arabia
An eco-friendly acetylcholine iodide-ethylene glycol (ACI/EG) deep eutectic mixture mediated green protocol has been developed for the synthesis of hitherto unexplored multi-functionalized linear tricyclic spiropyrrolo[1,2-]isoquinoline analogues. The effects of the synthesized compounds on the osteoblast differentiation of hBMSC-TERT cell lines were investigated and promising results were observed with significant IC values. In addition, molecular modeling simulations were also performed with the 3D structure of BMP-2 to reveal binding interactions and orientations of highly potent spiropyrrolo[1,2-]isoquinoline analogues.
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