New β-carboline derivatives containing imidazolium as potential VEGFR2 inhibitors: synthesis, X-ray structure, antiproliferative evaluations, and molecular modeling

Li, Ma; Chen, Xiaofei; Zhu, Siyu; Chen, Wei; Ma, Qin; Fan, Wenhong; Zhang, Jie; Guo, Liang

doi:10.1039/d2md00065b

Cited by 2 publications

(1 citation statement)

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“…The bioactivity of different indole derivatives was the subject of intensive studies. Just one example: a series of new β‐carboline derivatives (that incorporates the indole skeleton) fused with an imidazolium moiety was found to have a significant antitumor activity [5] . It may be concluded that the N ‐heterocyclic scaffolds selected by us have relevance in planning new derivatives with biological activity including a cytotoxic effect.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Activity of Phosphinoylated and Phosphonoylated N‐Heterocycles Obtained by the Microwave‐Assisted Palladium Acetate‐Catalyzed Hirao Reaction

Huszár,

Szolga,

Bősze

et al. 2023

Chemistry A European J

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A literature survey showed that different derivatives with the 9‐phenyl‐9H‐carbazole or the dihydroindoline scaffold may be of biological activity including cytotoxic effect. Driven by this experience, we wished to synthesize P‐functionalized derivatives of the above mentioned N‐heterocycles. Three N‐heterocycles, 9‐(4‐bromophenyl)‐9H‐carbazole, 3‐bromo‐9‐phenyl‐9H‐carbazole and 1‐(5‐bromoindolin‐1‐yl)ethan‐1‐one were coupled with dialkyl phosphites and diarylphosphine oxides using Pd(OAc)2 (10%) as the catalyst precursor and triethylamine as the base in ethanol under microwave irradiation. The excess of the Y2P(O)H reagent (Y = alkoxy, aryl) (30%) served as the P‐ligand in its trivalent tautomeric form (Y2POH), hence there was no need for the usual P‐ligands meaning cost and environmental burden. Hence, our method is a “green” approach that proved to be more efficient than the preparation by the traditional method. The products, dialkyl phosphonates and tertiary phosphine oxides obtained in 58–84% yields were characterized, one of them also by single crystal X‐ray analysis, and were subjected to in vitro biological activity evaluation. A (carbazol)yl‐phenylphosphonate, an N‐phenyl‐(carbazol)yl‐phosphonate, a (carbazol)yl‐phenylphosphine oxide and an N‐phenyl‐(carbazol)ylphosphine oxide revealed a significant cytotoxic activity on A549 human non‐small‐cell lung carcinoma and MonoMac‐6 acute monocytic leukemia cancer cells. The cytotoxic effect was significant as compared to that of the reference compounds.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Activity of Phosphinoylated and Phosphonoylated N‐Heterocycles Obtained by the Microwave‐Assisted Palladium Acetate‐Catalyzed Hirao Reaction

Huszár,

Szolga,

Bősze

et al. 2023

Chemistry A European J

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Design, synthesis and biological evaluation of novel β-carbolines as antitumor agents via targeting autophagy in colorectal cancer

Ao,

Lai,

et al. 2025

European Journal of Medicinal Chemistry

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New β-carboline derivatives containing imidazolium as potential VEGFR2 inhibitors: synthesis, X-ray structure, antiproliferative evaluations, and molecular modeling

Abstract: A series of new β-carboline derivatives containing an imidazolium moiety were designed and synthesized via the reaction of β-carboline-1-carboxaldehydes, acetyl chloride, primary amine, and formaldehyde. The antitumor activity of the...

Cited by 2 publications

References 48 publications

Synthesis and Anticancer Activity of Phosphinoylated and Phosphonoylated N‐Heterocycles Obtained by the Microwave‐Assisted Palladium Acetate‐Catalyzed Hirao Reaction

Synthesis and Anticancer Activity of Phosphinoylated and Phosphonoylated N‐Heterocycles Obtained by the Microwave‐Assisted Palladium Acetate‐Catalyzed Hirao Reaction

Design, synthesis and biological evaluation of novel β-carbolines as antitumor agents via targeting autophagy in colorectal cancer

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