Stereoselective Synthesis and Antiproliferative Activities of Tetrafunctional Diterpene Steviol Derivatives
A new family of diterpene-type aminotriol derivatives has been synthesised from stevioside in a stereoselective manner. The key intermediate spiro-epoxide was prepared through the methyl ester of the allilyc diol derived from steviol. The oxirane ring was opened with primary and secondary amines, pr...
Elmentve itt :
| Szerzők: | |
|---|---|
| Dokumentumtípus: | Cikk |
| Megjelent: |
2023
|
| Sorozat: | INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
24 No. 2 |
| Tárgyszavak: | |
| doi: | 10.3390/ijms24021121 |
| mtmt: | 33547781 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/26050 |
| LEADER | 02309nab a2200313 i 4500 | ||
|---|---|---|---|
| 001 | publ26050 | ||
| 005 | 20230110094111.0 | ||
| 008 | 230110s2023 hu o 0|| Angol d | ||
| 022 | |a 1661-6596 | ||
| 024 | 7 | |a 10.3390/ijms24021121 |2 doi | |
| 024 | 7 | |a 33547781 |2 mtmt | |
| 040 | |a SZTE Publicatio Repozitórium |b hun | ||
| 041 | |a Angol | ||
| 100 | 1 | |a Bai Dorottya | |
| 245 | 1 | 0 | |a Stereoselective Synthesis and Antiproliferative Activities of Tetrafunctional Diterpene Steviol Derivatives |h [elektronikus dokumentum] / |c Bai Dorottya |
| 260 | |c 2023 | ||
| 300 | |a 18 | ||
| 490 | 0 | |a INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES |v 24 No. 2 | |
| 520 | 3 | |a A new family of diterpene-type aminotriol derivatives has been synthesised from stevioside in a stereoselective manner. The key intermediate spiro-epoxide was prepared through the methyl ester of the allilyc diol derived from steviol. The oxirane ring was opened with primary and secondary amines, providing a versatile library of aminotriols. The corresponding primary aminotriol was formed by palladium-catalysed hydrogenation, and an N,O-heterocyclic compound was synthesised in a regioselective reaction. All new compounds were characterised by 1D- and 2D-NMR techniques and HRMS measurements. In our in vitro investigations, we found that the aromatic N-substituted derivatives exhibited high inhibition of cell growth on human cancer cell lines (HeLa, SiHa, A2780, MCF-7 and MDA-MB-231). The antiproliferative activities were assayed by the MTT method. Furthermore, the introduction of an additional hydroxy group slightly increased the biological activity. The drug-likeness of the compounds was assessed by in silico and experimental physicochemical characterisations, completed by kinetic aqueous solubility and in vitro intestinal-specific parallel artificial membrane permeability assay (PAMPA-GI) measurements. | |
| 650 | 4 | |a Általános orvostudomány | |
| 650 | 4 | |a Farmakológia és gyógyszerészet | |
| 700 | 0 | 1 | |a Schelz Zsuzsanna |e aut |
| 700 | 0 | 1 | |a Erdős Dóra |e aut |
| 700 | 0 | 1 | |a Kis Anna K. |e aut |
| 700 | 0 | 1 | |a Nagy Viktória |e aut |
| 700 | 0 | 1 | |a Zupkó István |e aut |
| 700 | 0 | 1 | |a Balogh György Tibor |e aut |
| 700 | 0 | 1 | |a Szakonyi Zsolt |e aut |
| 856 | 4 | 0 | |u http://publicatio.bibl.u-szeged.hu/26050/1/IntJMolSci_1121_Bai_2023.pdf |z Dokumentum-elérés |