Facile and high-yield synthesis of N-(4-diethylamino)benzyl-4-[11C]methoxy-N-(p-tolyl)benzenesulfonamide as a new potential PET selective CB2 radioligand

Mingzhang Gao, Julie Xu, Min Wang, Qi Huang Zheng

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The reference standard N-(4-diethylamino)benzyl-4-methoxy-N-(p-tolyl)benzenesulfonamide (3c) (CB2, Ki=0.5nM; CB1, Ki=1297nM; selectivity CB1/CB2=2594) and its corresponding precursor N-(4-diethylamino)benzyl-4-hydroxy-N-(p-tolyl)benzenesulfonamide (3d) were synthesized from 4-(diethylamino)benzaldehyde and p-toluidine in 3 steps with 75-84% overall chemical yield. The target tracer N-(4-diethylamino)benzyl-4-[11C]methoxy-N-(p-tolyl)benzenesulfonamide ([11C]3c) was synthesized from the phenol hydroxyl precursor by O-[11C]-methylation with [11C]CH3OTf, followed by HPLC combined with SPE purification in 40-50% decay corrected radiochemical yields with 370-740GBq/μmol specific activity at the end of bombardment (EOB).

Original languageEnglish (US)
Pages (from-to)181-186
Number of pages6
JournalApplied Radiation and Isotopes
Volume90
DOIs
StatePublished - Aug 2014

Keywords

  • Cancer
  • Cannabinoid receptor 2 (CB2)
  • Neurological disorders
  • Positron emission tomography (PET)
  • Radiosynthesis

ASJC Scopus subject areas

  • Radiation
  • Medicine(all)

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