Modified N,O-Nucleosides: Design, Synthesis, and Anti-tumour Activity

Abstract

A preliminary library of modified N,O-nucleosides was prepared and tested on a selected number of human cancer lines that include SKOV3, SW480, and K562. Thymine, N-benzyl substituents, and aromatic rings contribute to an increase of the biological activity, up to 10-25 mM, that appeared also reliant on the calculated lipophilicity of the nucleosides, expressed as cLogP, where P represents the partition coefficient of a solute between n-octanol and water. Scheme 1. Synthesis of N,O-nucleosides via 1,3-dipolar cycloaddition of nitrones 3 with vinyl nucleobases 4 by microwave (MW) irradiation. CSIRO PUBLISHINGAust.

Synthesis, Biological and In Silico Evaluation of Pure Nucleobase-Containing Spiro (Indane-Isoxazolidine) Derivatives as Potential Inhibitors of MDM2–p53 Interaction

“…Our group, with wide expertise of Mw-assisted reactions such as 1,3-dipolar cycloadditions [37,38,39,40,41], has recently synthesized a series of isatinyl/indanyl nitrones (INs) by a solvent-free condensation of alkyl- or arylhydroxylamines hydrochlorides with isatin and indanone using a microwave irradiation technique [42]. This methodology can be considered a versatile procedure to synthesize nitrones in high yields and a short reaction time, reducing the formation of by-products.…”

Antiproliferative activity of novel isatinyl/indanyl nitrones (INs) as potential spin trapping agents of free radical intermediates

“…18 In an attempt to generate novel molecular entities with amplified spin trapping and antiproliferative activity on cancer cells, we synthesized some isatin and indanone ketonitrones, combining the simultaneous presence of an oxindole-like ring and a nitrone portion. 18 In an attempt to generate novel molecular entities with amplified spin trapping and antiproliferative activity on cancer cells, we synthesized some isatin and indanone ketonitrones, combining the simultaneous presence of an oxindole-like ring and a nitrone portion.…”

C-5’-Triazolyl-2’-oxa-3’-aza-4’a-carbanucleosides: Synthesis and biological evaluation

“…In this context, nucleoside analogues, where different carbon or heterocyclic systems replace the furanose ring, have been reported as anticancer or antiviral agents [ 19 – 20 ]. In particular, 2’-oxa-3’-aza-4’a-carbanucleosides 1 – 4 , characterized by the presence of an isoxazolidine ring, represent a scaffold of modified dideoxynucleosides endowed with interesting physiological features ( Fig.…”