Kyle Rehrauer
Current Organizations / Institutes
The organizations/institutes from the scholar's latest article
Research Subjects
Research Interests
Kyle Rehrauer has a total of 10 co-authors. Here are the top co-authors by number of shared publications:
- Adrian E. Roitberg
University of Florida
1 shared publication - Alexander J. Grenning
University of Minnesota
1 shared publication - Anghelo Gangano
University of Florida
1 shared publication - Christopher W. Cunningham
Department of Pharmaceutical Sciences, Concordia University Wisconsin, Mequon, Wisconsin 53097, United States
1 shared publication - Daniel Barrus
RTI International
1 shared publication - Ion Ghiviriga
University of Florida
1 shared publication
Latest Publications
- Open Access
- 4 January 2023
- Published by American Chemical Society (ACS) in ChemRxiv
Axially Chiral Cannabinoids: Design, Synthesis, and Cannabinoid Receptor Affinity
The resorcinol-terpene phytocannabinoid template is a privileged scaffold for the development of diverse therapeutics target-ing the endocannabinoid system. Axially chiral cannabinols (axCBNs) are unnatural cannabinols (CBNs) that bear an addi-tional C10 substituent, which twists the cannabinol biaryl framework out of planarity creating an axis of chirality. This “es-cape from flatland” is hypothesized to enhance both the physical and biological properties of cannabinoid ligands, thus ush-ering in the next generation of endocannabinoid system chemical probes and cannabinoid-inspired leads for drug develop-ment. In this full report, we describe the philosophy guiding the design of axCBNs as well as several synthetic strategies for their construction. We also introduce a second class of axially chiral cannabinoids inspired by cannabidiol (CBD), termed axially chiral cannabidiols (axCBDs). Finally, we provide an analysis of axially chiral cannabinoid (axCannabinoid) atro-pisomerism, which spans two classes (class 1 and 3 atropisomers), and provide first evidence that axCannabinoids retain—and in some cases, strengthen—affinity and functional activity at cannabinoid receptors. Together, these findings present a promising new direction for the design of novel cannabinoid ligands for drug discovery and exploration of the complex en-docannabinoid system.
- 4 January 2023
- Published by American Chemical Society (ACS) in ChemRxiv
Open AccessAxially Chiral Cannabinoids: Design, Synthesis, and Cannabinoid Receptor Affinity
The resorcinol-terpene phytocannabinoid template is a privileged scaffold for the development of diverse therapeutics target-ing the endocannabinoid system. Axially chiral cannabinols (axCBNs) are unnatural cannabinols (CBNs) that bear an addi-tional C10 substituent, which twists the cannabinol biaryl framework out of planarity creating an axis of chirality. This “es-cape from flatland” is hypothesized to enhance both the physical and biological properties of cannabinoid ligands, thus ush-ering in the next generation of endocannabinoid system chemical probes and cannabinoid-inspired leads for drug develop-ment. In this full report, we describe the philosophy guiding the design of axCBNs as well as several synthetic strategies for their construction. We also introduce a second class of axially chiral cannabinoids inspired by cannabidiol (CBD), termed axially chiral cannabidiols (axCBDs). Finally, we provide an analysis of axially chiral cannabinoid (axCannabinoid) atro-pisomerism, which spans two classes (class 1 and 3 atropisomers), and provide first evidence that axCannabinoids retain—and in some cases, strengthen—affinity and functional activity at cannabinoid receptors. Together, these findings present a promising new direction for the design of novel cannabinoid ligands for drug discovery and exploration of the complex en-docannabinoid system.