Isatin-based spiro indolenine alkaloids from <i>Isatis indigotica</i> Fortune with anti-neuroinflammatory and acetylcholinesterase inhibitory effects

Bai, Ming; Xi, Yu-Fei; Mi, Si-Hui; Yang, Pei-Yuan; Lou, Li-Li; Lv, Tian-Ming; Zhang, Xin; Yao, Guo-Dong; Lin, Bin; Huang, Xiao-Xiao; Song, Shao-Jiang

doi:10.1039/d3qo01769a

Org. Chem. Front.

2024

DOI: 10.1039/d3qo01769a

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Isatin-based spiro indolenine alkaloids from Isatis indigotica Fortune with anti-neuroinflammatory and acetylcholinesterase inhibitory effects

Ming Bai,

Yu-Fei Xi,

Si-Hui Mi

et al.

Abstract: Compounds 1a/1b are a pair of enantiomers characterized by an unprecedented 6/5/6/5/6 N,O-heterocyclic scaffold with a unique spiro[4.5] core. Compound 2 is the first 6/5/6/5/5/6 hexacyclic skeleton fused with an unexpected dispiro[4.4.0.4] system.

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Cited by 3 publications

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Exploring plant-derived bisindole alkaloids: a comprehensive review of sources, phytochemistry and cytotoxicity

Zhang,

Li,

et al. 2024

Phytochem Rev

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Exploring plant-derived bisindole alkaloids: a comprehensive review of sources, phytochemistry and cytotoxicity

Zhang,

Li,

et al. 2024

Phytochem Rev

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Chiral synthetic unprecedented spiro[indoline-2,3′-thiophen]-3-ones via an organocatalytic asymmetric sulfa-Michael/aldol cascade reaction

Zhang,

Fei,

Yang

et al. 2024

Org. Chem. Front.

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Novel spirooxindole-triazole derivatives: unveiling [3+2] cycloaddition reactivity through molecular electron density theory and investigating their potential cytotoxicity against HepG2 and MDA-MB-231 cell lines

Shawish,

Al Ayoubi,

El-Faham

et al. 2024

Front. Chem.

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A novel analogue of hybrid spirooxindoles was synthesized employing a systematic multistep synthetic approach. The synthetic protocol was designed to obtain a series of spirooxindole derivatives incorporating triazolyl-s-triazine framework via [3 + 2] cycloaddition (32CA) reaction of azomethine ylide (AY) with the corresponding chalcones (6a-d). Unexpectedly, the reaction underwent an alternate route, leading to the cleavage of the s-triazine moiety and yielding a series of spirooxindole derivatives incorporating a triazole motif. A comprehensive investigation of the 32CA reaction mechanism was conducted using Molecular Electron Density Theory (MEDT). The viability of all compounds was evaluated through an MTT assay, and the IC50 values were determined using Prism Software. The antiproliferative efficacy of the synthesized chalcones and the corresponding spirooxindole derivatives was assessed against two cancer cell lines: MDA-MB-231 (triple-negative breast cancer) and HepG2 (human hepatoma). These findings were compared with Sorafenib, which was used as a positive control. The results revealed that chalcones (6c and 6d) were the most active among the tested chalcones, with IC50 values of 7.2 ± 0.56 and 7.5 ± 0.281 µM for (6c) and of 11.1 ± 0.37 and 11.0 ± 0.282 µM for (6d), against MDA-MB-231 and HepG2, respectively. Spirooxindoles (9b, 9c, 9h, and 9i) exhibited the highest activity with IC50 values ranging from 16.8 ± 0.37 µM to 31.3 ± 0.86 µM against MDA-MB-231 and 13.5 ± 0.92 µM to 24.2 ± 0.21 µM against HepG2. In particular, spirooxindole derivatives incorporating 2,4-dichlorophenyl moiety were the most active, with an IC50 of 16.8 ± 0.37 µM for (9h) against MDA-MB-23 and 13.5 ± 0.92 µM for (9i) against HepG2. Interestingly, the IC50 of compound (6c) (7.2 µM) exhibited better activity than that of Sorafenib (positive control) (9.98 µM) against MDA-MB-231. Molecular docking, ADMET, and molecular dynamic simulations were conducted for the promising candidates (6b, 6c, and 9h) to explore their binding affinity in the EGFR active site.

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Isatin-based spiro indolenine alkaloids from Isatis indigotica Fortune with anti-neuroinflammatory and acetylcholinesterase inhibitory effects

Abstract: Compounds 1a/1b are a pair of enantiomers characterized by an unprecedented 6/5/6/5/6 N,O-heterocyclic scaffold with a unique spiro[4.5] core. Compound 2 is the first 6/5/6/5/5/6 hexacyclic skeleton fused with an unexpected dispiro[4.4.0.4] system.

Cited by 3 publications

References 42 publications

Exploring plant-derived bisindole alkaloids: a comprehensive review of sources, phytochemistry and cytotoxicity

Exploring plant-derived bisindole alkaloids: a comprehensive review of sources, phytochemistry and cytotoxicity

Chiral synthetic unprecedented spiro[indoline-2,3′-thiophen]-3-ones via an organocatalytic asymmetric sulfa-Michael/aldol cascade reaction

Novel spirooxindole-triazole derivatives: unveiling [3+2] cycloaddition reactivity through molecular electron density theory and investigating their potential cytotoxicity against HepG2 and MDA-MB-231 cell lines

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