The Cu-catalyzed multicomponent ketone-amine-alkyne (KA2) reaction was combined with a Pauson-Khand cycloaddition to give access of unprecedented constrained spirocyclic pyrrolocyclopentenone derivatives following a DOS couple-pair approach. The polyfunctional molecular scaffolds were tested on the cyclopentenone reactivity to further expand the skeletal diversity, demonstrating the utility of this combined approach in generating novel spiro compounds as starting material for the generation of chemical libraries. The chemoinformatics characterization of the newly-synthesized molecules gave evidence about structural and physicochemical properties with respect to a set of blockbuster drugs, and showed that such scaffolds are drug-like but more spherical and three-dimensional in character than the drugs.

Combination of multicomponent KA2 and Pauson-Khand reactions: Short synthesis of spirocyclic pyrrolocyclopentenones / Innocenti R.; Lenci E.; Menchi G.; Trabocchi A.. - In: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1860-5397. - STAMPA. - 16(2020), pp. 200-211. [10.3762/bjoc.16.23]

Combination of multicomponent KA2 and Pauson-Khand reactions: Short synthesis of spirocyclic pyrrolocyclopentenones

Innocenti R.;Lenci E.;Menchi G.;Trabocchi A.
2020

Abstract

The Cu-catalyzed multicomponent ketone-amine-alkyne (KA2) reaction was combined with a Pauson-Khand cycloaddition to give access of unprecedented constrained spirocyclic pyrrolocyclopentenone derivatives following a DOS couple-pair approach. The polyfunctional molecular scaffolds were tested on the cyclopentenone reactivity to further expand the skeletal diversity, demonstrating the utility of this combined approach in generating novel spiro compounds as starting material for the generation of chemical libraries. The chemoinformatics characterization of the newly-synthesized molecules gave evidence about structural and physicochemical properties with respect to a set of blockbuster drugs, and showed that such scaffolds are drug-like but more spherical and three-dimensional in character than the drugs.
16
200
211
Goal 3: Good health and well-being
Innocenti R.; Lenci E.; Menchi G.; Trabocchi A.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2158/1189795
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