1-Substituted β-Carboline-3-Carboxylates with high affinities to the Benzodiazepine recognition site

Abstract

Naturally occurring derivatives of β-carboline-3-carboxylic acid bearing acetyl or vinyl groups at C-1 were prepared by Pd-catalyzed cross-coupling reactions of methyl 1-chloro-β-carboline-3-carboxylate with appropriate organostannanes. Esters with chloro or acetyl groups at C-1 showed high affinity for the brain benzodiazepine recognition site. Thus, in contrast to 1-alkyl and 1-aryl analogs, these β-carboline-3-carboxylates with electron-withdrawing substituents at C-1 show high affinities.

Keywords:

• Alkaloids
• β-Carbolines
• Cross-coupling reaction
• Benzodiazepine recognition site

Acknowledgments

This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie.

Notes

*This article is dedicated to Prof. Dr. H.-D. Stachel, Munich, on the occasion of his 75th birthday.

Additional information

Notes on contributors

Hanns Häberlein

*This article is dedicated to Prof. Dr. H.-D. Stachel, Munich, on the occasion of his 75th birthday.