Nortropane is a crucial scaffold found in biologically active alkaloids, including atropine, scopolamine, and cocaine, as well as in synthetic drug candidates like the FDA-approved anti-HIV drug Maraviroc [1-3]. Paired with the 1,3-oxazinan-2-one ring, a pharmacophore homologous to 1,3-oxazolidin-2-one, these spirocyclic hybrids possess immense potential for drug discovery and advanced materials design.
Our chemists have developed efficient and versatile methods for synthesizing exo- and endo-isomeric spirocyclic hybrids of the pharmacophoric (1R,5S)-8-azabicyclo[3.2.1]octane (nortropane) and 1,3-oxazinan-2-one fragments (see Figure 1). The results of the research performed have been presented in the latest publication by our scientific team [4].
Offered today is a collection of about 150 stock compounds from this series, with Custom Synthesis options available to tailor analogues meeting your specific research needs.
Please, contact us at orders@lifechemicals.com for any additional information and price quotations.
Key Benefits:
- Pharmacophoric Potential: The nortropane scaffold is well-known for its presence in biologically active compounds, making it a valuable starting point for designing therapeutically relevant molecules.
- Enhanced Drug-Like Properties: The inclusion of the 1,3-oxazinan-2-one fragment enhances chemical diversity, making these hybrids ideal candidates for lead optimization in various therapeutic areas.
- Broad Applications: These compounds hold promise in areas like CNS drug discovery, antiviral research, and receptor-targeted therapies.
Figure 1. Synthetic scheme and examples of final products.
Representative screening compounds from the Screening Library
Reference:
- Kohnen-Johannsen, K. L.; Kayser, O. Molecules 2019, 24, 796.
- Buels, K. S.; Fryer, A. D. In Muscarinic Receptors, Handbook of Experimental Pharmacology 208; Fryer, A. D.; Christopoulos, A.; Nathanson, N. M., Ed.; Springer: Berlin, 2012, 317–341.
- Mandala, D.; Thompson, W. A.; Watts, P. Tetrahedron 2016, 72, 3389.
- Spirocyclic Hybrids of Nortropane and 1,3-Oxazinan-2-one Fragments. A. Mandzhulo, I. Vashchenko, O. Lukin, S. Shishkina, G. Dolgonos, A. Gerasov, V. Yepishev, D. Samofalova, V. Fetyukhin, A. Shivanyuk. Synthesis 2024; 56(17): 2709-2730. DOI: 10.1055/a-2335-4444