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Mendeleev Commun., 2025 Volume 35, Issue 5, Pages 518–520 (Mi mendc7269)

Communications

Functionalization of terpene alcohols with 1-sulfonyl-1,2,3-triazoles: synthesis of N-(2-terpenyloxyethenyl/ethyl)sulfonamides

D. S. Vasilchenkoab, M. V. Shafeevaa, E. V. Rogachevac, L. A. Kraevac, A. S. Bunevd, T. P. Tretyakovad, L. S. Chistyie, N. V. Rostovskiib, Yu. G. Trishina

a St. Petersburg State University of Industrial Technologies and Design, 198095 St. Petersburg, Russian Federation
b Institute of Chemistry, St. Petersburg State University, 199034 St. Petersburg, Russian Federation
c St. Petersburg Pasteur Institute, 197101 St. Petersburg, Russian Federation
d Medicinal Chemistry Center, Togliatti State University, 445020 Togliatti, Russian Federation
e Research Institute of Hygiene, Occupational Pathology and Human Ecology, Federal Medical Biological Agency, 188663 Leningrad Region, Russian Federation

Abstract: New N-(2-aryl-2-terpenyloxyethenyl)sulfonamides bearing two pharmacophoric terpenyloxy and sulfonamide groups linked through an ethylene bridge were synthesized by the reaction of p-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 N-(2-aryl-2-terpenyloxyethyl)-sulfonamides. Some of the synthesized compounds exhibited high antibacterial and moderate cytotoxic activity.

Keywords: terpene alcohols, 1,2,3-triazoles, rhodium(II) pivalate, azavinylcarbenes, OH insertion reactions, sulfonamides, antibacterial activity, cytotoxic activity.

Received: 18.12.2024
Accepted: 27.02.2025

Language: English

DOI: 10.71267/mencom.7712



© Steklov Math. Inst. of RAS, 2025