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 journalArticle

6 Citations (Scopus)

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

Fingerprint

methylation
synthesis
purification
phenols
tracers
bombardment
selectivity
Phenol
Hydroxyl Radical
Methylation
decay
High Pressure Liquid Chromatography
benzenesulfonamide
4-toluidine
4-(diethylamino)benzaldehyde

Keywords

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

ASJC Scopus subject areas

  • Radiation
  • Medicine(all)

Cite this

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title = "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",
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).",
keywords = "Cancer, Cannabinoid receptor 2 (CB2), Neurological disorders, Positron emission tomography (PET), Radiosynthesis",
author = "Mingzhang Gao and Julie Xu and Min Wang and Qi-Huang Zheng",
year = "2014",
doi = "10.1016/j.apradiso.2014.03.029",
language = "English",
volume = "90",
pages = "181--186",
journal = "Applied Radiation and Isotopes",
issn = "0969-8043",
publisher = "Elsevier Limited",

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TY - JOUR

T1 - 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

AU - Gao, Mingzhang

AU - Xu, Julie

AU - Wang, Min

AU - Zheng, Qi-Huang

PY - 2014

Y1 - 2014

N2 - 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).

AB - 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).

KW - Cancer

KW - Cannabinoid receptor 2 (CB2)

KW - Neurological disorders

KW - Positron emission tomography (PET)

KW - Radiosynthesis

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