The isocyanide stands out as an intriguing entity, owing to its chameleonic reactivity that has made it a widely utilized reactant in organic synthesis, especially in multicomponent reactions (MCRs). Despite its pivotal role in the biological activity of natural compounds, isocyanides have historically been overlooked by medicinal chemists due to misconceptions about their toxicity, reactivity, and metabolic instability. Additionally, the structural complexity and limited availability of natural isocyanides have contributed to this neglect. However, our recent investigations have revealed that, under specific molecular contexts, the isocyanide group can resist human metabolism and show promise as a pharmacophoric group in medicinal chemistry. Therefore, the aim of this PhD was to systematically utilize the isocyanide as a pharmacophoric group, integrating it into chemically straightforward and expeditiously synthesized structures, with the goal of deploy them in medicinal chemistry screening campaigns, particularly within the domains of antimicrobial and oncological research. Another goal was to develop environmental friendly synthetic procedures for the synthesis and use of isocyanides.

Green methodologies for the synthesis and use of isocyanides and their application in medicinal chemistry

BRUNELLI, FRANCESCA
2025

Abstract

The isocyanide stands out as an intriguing entity, owing to its chameleonic reactivity that has made it a widely utilized reactant in organic synthesis, especially in multicomponent reactions (MCRs). Despite its pivotal role in the biological activity of natural compounds, isocyanides have historically been overlooked by medicinal chemists due to misconceptions about their toxicity, reactivity, and metabolic instability. Additionally, the structural complexity and limited availability of natural isocyanides have contributed to this neglect. However, our recent investigations have revealed that, under specific molecular contexts, the isocyanide group can resist human metabolism and show promise as a pharmacophoric group in medicinal chemistry. Therefore, the aim of this PhD was to systematically utilize the isocyanide as a pharmacophoric group, integrating it into chemically straightforward and expeditiously synthesized structures, with the goal of deploy them in medicinal chemistry screening campaigns, particularly within the domains of antimicrobial and oncological research. Another goal was to develop environmental friendly synthetic procedures for the synthesis and use of isocyanides.
2025
Inglese
TRON, Gian Cesare
Università degli Studi del Piemonte Orientale Amedeo Avogadro
Vercelli
291
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.14242/218108
Il codice NBN di questa tesi è URN:NBN:IT:UNIUPO-218108