Regioselective synthesis and cannabinoid receptor binding affinity of N-Alkylated 4,5-Diaryl-1,2,3-triazoles

Murali Papudippu, Hong Shu, Sari Izenwasser, Dean Wade, Gerard Gulasey, Steven Fournet, Edwin D. Stevens, Stacey A. Lomenzo, Mark L. Trudell

Research output: Contribution to journalArticle

2 Scopus citations

Abstract

A series of N1- and N2-substituted 4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-1,2,3-triazoles were regioselectively synthesized to explore the binding motifs of the diaryl-1,2,3-triazole scaffold at CB1 receptors. The N1 analogs were regioselectively constructed via Click chemistry to furnish analogs with modest CB1 receptor affinity (K i < 200 nM). The regioselective N2-alkylation of the 4-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-1,2,3-triazole afforded analogs that exhibited good affinity for CB1 receptors (K i < 100 nM).

Original languageEnglish (US)
Pages (from-to)4473-4484
Number of pages12
JournalMedicinal Chemistry Research
Volume21
Issue number12
DOIs
StatePublished - Dec 1 2012

Keywords

  • 1,2,3-triazole
  • Cannabinoid receptors
  • Click chemistry
  • N-alkylation

ASJC Scopus subject areas

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

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    Papudippu, M., Shu, H., Izenwasser, S., Wade, D., Gulasey, G., Fournet, S., Stevens, E. D., Lomenzo, S. A., & Trudell, M. L. (2012). Regioselective synthesis and cannabinoid receptor binding affinity of N-Alkylated 4,5-Diaryl-1,2,3-triazoles. Medicinal Chemistry Research, 21(12), 4473-4484. https://doi.org/10.1007/s00044-012-9991-3