Stereoselective Synthesis and Antiproliferative Activity of Steviol-Based Diterpene 1,3-Aminoalcohol Regioisomers
A series of novel diterpene-type 1,3-aminoalcohols and their regioisomers have been synthesised from natural stevioside in a stereoselective manner. The key intermediate β-keto alcohol was prepared using Wagner–Meerwein rearrangement of the epoxide derived from steviol methyl ester. The primary amin...
Elmentve itt :
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| Dokumentumtípus: | Cikk |
| Megjelent: |
2023
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| Sorozat: | MOLECULES
28 No. 24 |
| Tárgyszavak: | |
| doi: | 10.3390/molecules28247962 |
| mtmt: | 34417276 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/29006 |
| LEADER | 01994nab a2200265 i 4500 | ||
|---|---|---|---|
| 001 | publ29006 | ||
| 005 | 20231207081024.0 | ||
| 008 | 231207s2023 hu o 0|| Angol d | ||
| 022 | |a 1420-3049 | ||
| 024 | 7 | |a 10.3390/molecules28247962 |2 doi | |
| 024 | 7 | |a 34417276 |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 Activity of Steviol-Based Diterpene 1,3-Aminoalcohol Regioisomers |h [elektronikus dokumentum] / |c Bai Dorottya |
| 260 | |c 2023 | ||
| 300 | |a 22 | ||
| 490 | 0 | |a MOLECULES |v 28 No. 24 | |
| 520 | 3 | |a A series of novel diterpene-type 1,3-aminoalcohols and their regioisomers have been synthesised from natural stevioside in a stereoselective manner. The key intermediate β-keto alcohol was prepared using Wagner–Meerwein rearrangement of the epoxide derived from steviol methyl ester. The primary aminoalcohol was formed via Raney-nickel-catalysed hydrogenation of an oxime, and a versatile library of aminoalcohols was synthesised using a Schiff base with the primary amines. The aminoalcohol regioisomers were prepared from the mesylate of the β-keto alcohols. The corresponding primary aminoalcohol was formed via the palladium-catalysed hydrogenation of hydroxyl-azide, and click reactions of the latter were also carried out. The new compounds were characterised using 1D- and 2D-NMR techniques and HRMS measurements. The in vitro investigations showed high inhibition of cell growth in human cancer cell lines (HeLa, SiHa, A2780, MCF-7 and MDA-MB-231) in the case of naphthalic N-substituted derivatives. The antiproliferative effects were assayed using the MTT method. | |
| 650 | 4 | |a Farmakológia és gyógyszerészet | |
| 700 | 0 | 1 | |a Schelz Zsuzsanna |e aut |
| 700 | 0 | 1 | |a Boncz Mária Fanni |e aut |
| 700 | 0 | 1 | |a Zupkó István |e aut |
| 700 | 0 | 1 | |a Szakonyi Zsolt |e aut |
| 856 | 4 | 0 | |u http://publicatio.bibl.u-szeged.hu/29006/1/Molecules_7962_Bai_2023.pdf |z Dokumentum-elérés |