Non-Catalyzed Click Reactions of ADIBO Derivatives with 5-Methyluridine Azides and Conformational Study of the Resulting Triazoles

PLoS One. 2015 Dec 16;10(12):e0144613. doi: 10.1371/journal.pone.0144613. eCollection 2015.

Abstract

Copper-free click reactions between a dibenzoazocine derivative and azides derived from 5-methyluridine were investigated. The non-catalyzed reaction yielded both regioisomers in an approximately equivalent ratio. The NMR spectra of each regioisomer revealed conformational isomery. The ratio of isomers was dependent on the type of regioisomer and the type of solvent. The synthesis of various analogs, a detailed NMR study and computational modeling provided evidence that the isomery was dependent on the interaction of the azocine and pyrimidine parts.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azoles / chemistry*
  • Click Chemistry*
  • Copper / chemistry
  • Molecular Conformation*
  • Nuclear Magnetic Resonance, Biomolecular
  • Triazoles / chemistry*

Substances

  • Azoles
  • Triazoles
  • Copper

Grants and funding

The research in this project was supported by the Ministry of Education, Youth and Sport of the Czech Republic (project IGA_PrF_2015_007), Technological Agency CR (project TE01020028) and by the European Social Fund (CZ.1.07/2.3.00/20.0009). The infrastructure of this project (Institute of Molecular and Translation Medicine) was supported by the National Program of sustainability (project LO1304). Computational resources were provided by the MetaCentrum under the program LM2010005 and the CERIT-SC under the program Centre CERIT Scientific Cloud, part of the Operational Program Research and Development for Innovations, Reg. no. CZ.1.05/3.2.00/08.0144.