Article 2023 · 31 atıf

Synthesis of nitrogen-containing oleanolic acid derivatives as carbonic anhydrase and acetylcholinesterase inhibitors

Senol, Halil, Turgut, Gurbet Celik, Sen, Alaattin, Saglamtas, Rueya, Tuncay, Salih, Gulcin, Ilhami, Topcu, Guelacti

Özet

In this study, a total of 13 compounds (5-17) were synthesized starting from oleanolic acid (OA), a natural triterpenoid. Five new compounds (10, 11, 12, 15 and 17), are the main targets of the study, which were synthesized for the first time in this work as oxime, imine and hydrazone derivatives of OA. Other compounds were previously obtained as natural or semi-synthetically. NMR and HRMS analyses were carried out to determine of structures of all the synthesized molecules. The inhibitory effects of the synthesized compounds on acetylcholinesterase (AChE), human carbonic anhydrase I (hCA I) and II (hCA II) were evaluated. Compounds 13 and 15 showed better inhibitory activity than the other compounds against both hCA I and hCA II isoenzymes, which are competing with AZA. In addition, compound 15 showed the strongest AChE inhibitory activity among all the tested compounds, with an IC50 value of 34.46 mu M.

Anahtar Kelimeler

Oleanolic acid Acetylcholinesterase Oxime Imine Hydrazone Carbonic anhydrase BIOLOGICAL EVALUATION CRYSTAL-STRUCTURE ALPHA-GLUCOSIDASE URSOLIC ACIDS ISOENZYMES I BUTYRYLCHOLINESTERASE TRITERPENOIDS GLYCOSIDASE DEMENTIA ANALOGS

WoS Kategorileri

Chemistry, Medicinal

Sürdürülebilir Kalkınma Amaçları

Sağlık ve Kaliteli Yaşam

Künye

Dergi: MEDICINAL CHEMISTRY RESEARCH
Yıl: 2023
Cilt: 32
Sayı: 4
Sayfa: 694-704
ISSN: 1054-2523
eISSN: 1554-8120
DOI: 10.1007/s00044-023-03031-z
WoS UID: WOS:000933217400001

Yayını aç (DOI)