951892-01-6Relevant academic research and scientific papers
Selective Acylation of Aryl- A nd Heteroarylmagnesium Reagents with Esters in Continuous Flow
Heinz, Benjamin,Djukanovic, Dimitrije,Ganiek, Maximilian A.,Martin, Benjamin,Schenkel, Berthold,Knochel, Paul
, p. 493 - 496 (2020/01/31)
A selective acylation of readily accessible organomagnesium reagents with commercially available esters proceeds at convenient temperatures and short residence times in continuous flow. Flow conditions allow us to prevent premature collapse of the hemiacetal intermediates despite noncryogenic conditions, thus furnishing ketones in good yields. Throughout, the coordinating ability of the ester and/or Grignard was crucial for the reaction outcome. This was leveraged by the obtention of several bisaryl ketones using 2-hydroxy ester derivatives as substrates.
Exploring the substituent effects on a novel series of C1′-dimethyl-aryl Δ8-tetrahydrocannabinol analogs
Krishnamurthy, Mathangi,Gurley, Steven,Moore II, Bob M.
, p. 6489 - 6500 (2008/12/21)
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.
