Exploring the substituent effects on a novel series of C1′-dimethyl-aryl Δ8-tetrahydrocannabinol analogs

Mathangi Krishnamurthy, Steven Gurley, Bob Moore

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The synthesis and characterization of novel C1′-phenyl-substituted Δ8-THC analogs were previously reported by our laboratory. Within this small series of compounds, the C1′-dimethyl phenyl group was found to impart 13.5-fold selectivity for the CB2 receptor with a Ki 0.91 nM. The current study expands on the previous report by evaluating the effects of aromatic ring substitution on CB1 and CB2 receptor subtype binding and selectivity. The ring substituents synthesized in this study include aliphatic, halogen, nitrile, and acetamido functional groups. In addition, the isosteric replacement of the phenyl group by thiophene was evaluated. The anti-glioma activities of selected compounds were evaluated in vitro and compared to the lead compound 2.

Original languageEnglish (US)
Pages (from-to)6489-6500
Number of pages12
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number13
DOIs
StatePublished - Jul 1 2008

Fingerprint

Cannabinoid Receptor CB2
Dronabinol
Lead compounds
Cannabinoid Receptor CB1
Thiophenes
Nitriles
Halogens
Glioma
Functional groups
Substitution reactions
Lead
In Vitro Techniques

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Exploring the substituent effects on a novel series of C1′-dimethyl-aryl Δ8-tetrahydrocannabinol analogs. / Krishnamurthy, Mathangi; Gurley, Steven; Moore, Bob.

In: Bioorganic and Medicinal Chemistry, Vol. 16, No. 13, 01.07.2008, p. 6489-6500.

Research output: Contribution to journalArticle

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