Functionalization of terpene alcohols with 1-sulfonyl-1,2,3-triazoles: synthesis of <em>N</em>-(2-terpenyloxyethenyl/ethyl)sulfonamides
New <em>N</em>-(2-aryl-2-terpenyloxyethenyl)sulfonamides bearing two pharmacophoric terpenyloxy and sulfonamide groups linked through an ethylene bridge were synthesized by the reaction of <em>p</em>-menthol, allobetulin or isoborneol with 4-aryl-1-arylsulfonyl-1,2,3-triazoles in the presence of rhodium(II) pivalate. A significant part of the compounds obtained possessed low stability, which necessitated their hydrogenation into more stable <em>N</em>-(2-aryl-2-terpenyloxyethyl)-sulfonamides. Some of the synthesized compounds exhibited high antibacterial and moderate cytotoxic activity.
Authors
- Tatyana Tretyakova (ORCID: https://orcid.org/0000-0003-2916-8678)
- Leonid S. Chistyi
- Л. А. Краева (ORCID: https://orcid.org/0000-0002-9115-3250)
- Николай В. Ростовский (ORCID: https://orcid.org/0000-0002-8925-794X)
- Dmitrii S. Vasilchenko (ORCID: https://orcid.org/0009-0000-1371-5003)
- Elizaveta Rogacheva (ORCID: https://orcid.org/0000-0002-3843-0685)
- M. V. Shafeeva
- Alexander S. Bunev (ORCID: https://orcid.org/0000-0001-6408-8329)
- Yury Georgievich Trishin
Institutions
- St Petersburg University (RU)
- Togliatti State University (RU)
- Saint-Petersburg State University of Technology and Design (RU)
- Saint Petersburg Pasteur Institute (RU)
- Federal Medical-Biological Agency (RU)
Publication Details
- Journal
- Mendeleev Communications
- Published
- 2025-01-01
- DOI
- https://doi.org/10.71267/mencom.7712
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Saint Petersburg State University
- Russian Science Foundation
- Division of Materials Research