Highly Efficient Synthesis of Spiro[1-azabicyclo[3.2.0]heptane] Frameworks via [3+2]-Cycloaddition

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 27, 2025

An efficient one-pot three-component [3 + 2]-cycloaddition reaction of azomethine ylides, generated in situ from isatins and azetidine-2-carboxylic acid, with different maleimides itaconimides has been investigated. These reactions afford the corresponding spiro dispiro[1-azabicyclo[3.2.0]heptanes] moderate to high yields (up 93%) excellent diastereoselectivities regioselectivities under mild conditions. The method provides a simple route stereoselective synthesis new polyheterocyclic systems such as 3-spiro[1-azabicyclo[3.2.0]heptane]oxindoles spiro-conjugated or fused succinimide moiety. observed diastereo- regioselectivity cycloaddition is reasoned by DFT studies. antiproliferative effect synthesized compounds against cancer cell lines was assessed.

Язык: Английский

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In Vitro Activity of Pyrrolo[3, 4-D]Isoxazoles Against Hela, 3T3 and 3T3-SV40 Cell Lines

Pharmaceutical Chemistry Journal, Год журнала: 2025, Номер unknown

Опубликована: Фев. 22, 2025

Язык: Английский

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Study of Cytotoxicity of 3-Azabicyclo[3.1.0]hexanes and Cyclopropa[a]pyrrolizidines Spiro-Fused to Acenaphthylene-1(2H)-one and Aceanthrylene-1(2H)-one Fragments Against Tumor Cell Lines

International Journal of Molecular Sciences, Год журнала: 2025, Номер 26(8), С. 3474 - 3474

Опубликована: Апрель 8, 2025

A series of 3-azabicyclo[3.1.0]hexanes and cyclopropa[a]pyrrolizidines spiro-fused to acenaphthylene-1(2H)-one aceanthrylene-1(2H)-one frameworks have been studied for their in vitro antiproliferative activity against human erythroleukemia (K562), cervical carcinoma (HeLa), melanoma (Sk-mel-2), osteosarcoma (U2OS), as well murine (B16) cell lines. Using confocal microscopy, it was found that cultivation with the tested compounds led disappearance stress fibers (granular actin distributed diffusely cytoplasm up 56% treated cells) decrease filopodia-like deformations (up 69% after cultivation), which indirectly suggests a motility. The line scratch test showed these cells lose ability move do not fill scratched strip. This also supported by docking simulations actin-related targets (PDB ID: 8DNH, 2Q1N). flow cytometry, impact on mitochondrial membrane potential significant increase number decreased from 10% control 55-80% cyclopropa[a]pyrrolizidine adducts. obtained results support antitumor effect spiro-compounds encourage extension study order improve anticancer reduce toxicological risks.

Язык: Английский

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Organocatalytic Diastereoselective Synthesis of Spiro[3-azabicyclo[3.1.0]hexanes] via 1,3-Dipolar Cycloaddition of Azomethine Ylides with Cyclopropenes

Russian Journal of General Chemistry, Год журнала: 2024, Номер 94(4), С. 804 - 823

Опубликована: Апрель 1, 2024

Язык: Английский

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