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

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

Dmitrii Sergeevich Vasilchenko 1, 2
Dmitrii Sergeevich Vasilchenko
, 
Maria Vladimirovna Shafeeva 1
Maria Vladimirovna Shafeeva
, 
Elizaveta Vladimirovna Rogacheva 3
Elizaveta Vladimirovna Rogacheva
, 
Lyudmila Aleksandrovna Kraeva 3
Lyudmila Aleksandrovna Kraeva
,  , 
Tatyana Petrovna Tretyakova 4
Tatyana Petrovna Tretyakova
, 
Leonid Sergeevich Chistyi 5
Leonid Sergeevich Chistyi
, 
Nikolay Vitalyevich Rostovskii 2
Nikolay Vitalyevich Rostovskii
, 
Yury Georgievich Trishin 1
Yury Georgievich Trishin
1 St. Petersburg State University of Industrial Technologies and Design, 198095 St. Petersburg, Russian Federation
3 St. Petersburg Pasteur Institute, 197101 St. Petersburg, Russian Federation
4 Medicinal Chemistry Center, Togliatti State University, 445020 Togliatti, Russian Federation
5 Research Institute of Hygiene, Occupational Pathology and Human Ecology, Federal Medical Biological Agency, 188663 Leningrad Region, Russian Federation
10.71267/mencom.7712
Published 2025-07-17
Communication , Volume 35, Issue 5, 518-520
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Vasilchenko D. S. et al. Functionalization of terpene alcohols with 1-sulfonyl-1,2,3-triazoles: synthesis of N-(2-terpenyloxyethenyl/ethyl)sulfonamides // Mendeleev Communications. 2025. Vol. 35. No. 5. pp. 518-520.
GOST all authors (up to 50) Copy
Vasilchenko D. S., Shafeeva M. V., Rogacheva E. V., Kraeva L. A., Bunev A. S., Tretyakova T. P., Chistyi L. S., Rostovskii N. V., Trishin Y. G. Functionalization of terpene alcohols with 1-sulfonyl-1,2,3-triazoles: synthesis of N-(2-terpenyloxyethenyl/ethyl)sulfonamides // Mendeleev Communications. 2025. Vol. 35. No. 5. pp. 518-520.
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TY - JOUR
DO - 10.71267/mencom.7712
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7712
TI - Functionalization of terpene alcohols with 1-sulfonyl-1,2,3-triazoles: synthesis of N-(2-terpenyloxyethenyl/ethyl)sulfonamides
T2 - Mendeleev Communications
AU - Vasilchenko, Dmitrii Sergeevich
AU - Shafeeva, Maria Vladimirovna
AU - Rogacheva, Elizaveta Vladimirovna
AU - Kraeva, Lyudmila Aleksandrovna
AU - Bunev, Alexander Siyasatovich
AU - Tretyakova, Tatyana Petrovna
AU - Chistyi, Leonid Sergeevich
AU - Rostovskii, Nikolay Vitalyevich
AU - Trishin, Yury Georgievich
PY - 2025
DA - 2025/07/17
PB - Mendeleev Communications
SP - 518-520
IS - 5
VL - 35
ER -
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@article{2025_Vasilchenko,
author = {Dmitrii Sergeevich Vasilchenko and Maria Vladimirovna Shafeeva and Elizaveta Vladimirovna Rogacheva and Lyudmila Aleksandrovna Kraeva and Alexander Siyasatovich Bunev and Tatyana Petrovna Tretyakova and Leonid Sergeevich Chistyi and Nikolay Vitalyevich Rostovskii and Yury Georgievich Trishin},
title = {Functionalization of terpene alcohols with 1-sulfonyl-1,2,3-triazoles: synthesis of N-(2-terpenyloxyethenyl/ethyl)sulfonamides},
journal = {Mendeleev Communications},
year = {2025},
volume = {35},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7712},
number = {5},
pages = {518--520},
doi = {10.71267/mencom.7712}
}
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Vasilchenko, Dmitrii Sergeevich, et al. “Functionalization of terpene alcohols with 1-sulfonyl-1,2,3-triazoles: synthesis of N-(2-terpenyloxyethenyl/ethyl)sulfonamides.” Mendeleev Communications, vol. 35, no. 5, Jul. 2025, pp. 518-520. https://mendcomm.colab.ws/publications/10.71267/mencom.7712.

Keywords

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

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.

Funders

Russian Science Foundation
22-73-10184