Synthesis, Structure, and Antiviral Activity of Camphene‐Based Spiroisoxazolines
Abstract 1,3‐Dipolar cycloaddition reactions of nitrile oxides to camphene were studied. Slow diffusion of DIPEA vapor into a solution containing N‐hydroxyimidoyl halide as a precursor of 1,3‐dipole was used to effectively generate unstable nitrile oxides. For the first time, the regio‐ and stereoselectivity of the nitrile oxides cycloaddition to camphene was established: 1,3‐dipoles add from the exo side of C═C double bond with the formation of 5‐spiro oxazolidines. Synthesized spiroisoxazolidines were tested for antiviral activity against the influenza A virus of H1N1 subtype; compounds with a reasonable inhibitory effect and selectivity were revealed.
Authors
- Maria A. Niukalova (ORCID: https://orcid.org/0000-0003-1553-2643)
- Dmitry E. Shybanov (ORCID: https://orcid.org/0009-0009-5892-4074)
- Elena Kimovna Beloglazkina (ORCID: https://orcid.org/0000-0001-6796-8241)
- Оlga I. Yarovaya (ORCID: https://orcid.org/0000-0002-2333-4893)
- Nikolai Vasil'evich Zyk (ORCID: https://orcid.org/0000-0002-3771-116X)
- Yuri K. Grishin (ORCID: https://orcid.org/0000-0001-7709-5245)
- Нариман Ф. Салахутдинов (ORCID: https://orcid.org/0000-0001-8512-4309)
- Владимир В. Зарубаев (ORCID: https://orcid.org/0000-0002-6837-5242)
- Vitaly A. Roznyatovsky
- Angelica V. Garshinina
Institutions
- Lomonosov Moscow State University (RU)
- Novosibirsk Institute of Organic Chemistry (RU)
- Saint Petersburg Pasteur Institute (RU)
- Moscow State University (TJ)
Publication Details
- Journal
- ChemistrySelect
- Published
- 2025-09-01
- DOI
- https://doi.org/10.1002/slct.202503734
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Russian Science Foundation