Isolation of Antiplasmodial Oxazoles and Isoflavonoids from the Roots of Oxytropis trichophysa and Total Synthesis of Oxazole-type Alkaloids

Journal of Natural Products, Год журнала: 2025, Номер unknown

Опубликована: Янв. 18, 2025

A chemical examination of a root extract Oxytropis trichophysa led to the isolation and identification 23 compounds, including oxazole-type alkaloids isoflavonoid derivatives. Notably, three (1, 2, 3) two derivatives (7 10) were obtained from natural source for first time. In addition, O. derived 2,5-diphenyloxazoles their synthesized. Despite potential activity, antiplasmodial activities naturally occurring certain isoflavonoids remain unexplored. Therefore, both synthesized compounds evaluated against Plasmodium falciparum strain 3D7. Among tested 5, 6), one alkaloid (34), (13 15) demonstrated significant inhibitory effects, with half-maximal concentration (IC50) values ranging 3.1 6.2 μM selective indices between 0.9 18.8. Compound 1 showed most potent an IC50 μM, while its cytotoxic 50% value human foreskin fibroblasts was found be 8.5 μM. The isolated this plant provide valuable insights into composition may help elucidate properties trichophysa.

Язык: Английский

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Molecular Iodine-Catalyzed Synthesis of 3,3-Disubstituted Isatins: Total Synthesis of Indole Alkaloid, 3,3-Dimethoxy-2-oxindole

Chemistry, Год журнала: 2025, Номер 7(2), С. 43 - 43

Опубликована: Март 17, 2025

3,3-Dialkoxy-2-oxindoles are prevalent in natural products and exhibit unique biological activities. Among them, acyclic alkoxy analogues show instability acidic conditions, making access to isatin ketals highly challenging. Conventional methods for the synthesis of 3,3-dialkoxy-2-oxindoles usually require strongly harsh reaction resulting a low overall efficiency. Herein, we report on an acid- metal-free protocol from isatins through iodine-catalyzed ketalization. This photochemical does not use any specific reagents such as metal catalysts. Furthermore, total unprecedented 2-oxindole alkaloid bearing 3,3-dimethoxy moiety is achieved.

Язык: Английский

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Total Synthesis of the Proposed Structure of Indolyl 1,2-Propanediol Alkaloid, 1-(1H-Indol-3-yloxy)propan-2-ol

Chemistry, Год журнала: 2023, Номер 5(4), С. 2772 - 2784

Опубликована: Дек. 12, 2023

The first total synthesis of the proposed structure unprecedented indolyl derivative bearing 1,2-propanediol moiety is described. Isomerization 3-alkoxyindolines through indolenium intermediates was key step in synthesis. 1H, 13C-NMR, IR, and HRMS spectra synthetic compound drastically differed to those originally reported structure, which suggests natural product requires revision.

Язык: Английский

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