Novel diaryl-2H-azirines: Antitumor hybrids for dual-targeting tubulin and DNA

Lin, Shibo; Liang, Yuru; Cheng, Jing; Pan, Feng; Wang, Yang

doi:10.1016/j.ejmech.2021.113256

European Journal of Medicinal Chemistry

2021

DOI: 10.1016/j.ejmech.2021.113256

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Novel diaryl-2H-azirines: Antitumor hybrids for dual-targeting tubulin and DNA

Shibo Lin

Yuru Liang

Jing Cheng

et al.

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Cited by 11 publications

(1 citation statement)

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“…A promising strategy for olefin bond stabilization is to fix it by a heterocyclic moiety. At the moment, many analogues of CA-4 have been developed based on a wide range of heterocycles, among which are three-, , four-, , five-, ,− six-membered ,, and other − heterocyclic analogues of CA-4.…”

mentioning

confidence: 99%

3,4-Diarylisoxazoles─Analogues of Combretastatin A-4: Design, Synthesis, and Biological Evaluation In Vitro and In Vivo

Karetnikov,

Vasilyeva,

Babayeva

et al. 2024

ACS Pharmacol. Transl. Sci.

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Focusing on the molecular docking results, a series of 3,4-diarylisoxazoles, analogues of Combretastatin A4, bearing various substituents at the fifth position of the isoxazole ring and pharmacophore groups bioisosteric to methoxy substituent at ring B, were synthesized in good yields and high regioselectivity. Depending on the substituent at C5, three approaches were chosen for the construction of isoxazole ring, including nitrosation of gemdihalocyclopropanes, nitrile oxide synthesis, and difluoromethoxylation of isoxazolone to afford 5-haloisoxazoles, 5-unsubstituted isoxazoles, and 5-difluoromethoxyisoxazoles, respectively. Isoxazoles 43 and 45 showed selective cytotoxicity and antitubulin inhibition properties in vitro, with pharmacodynamic profiles closely related to that of CA-4. Both of them slow down tumor growth (66−74%) in mouse xenografts and slightly exceed in effectiveness Combretastatin A4-phosphate itself.

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confidence: 99%

3,4-Diarylisoxazoles─Analogues of Combretastatin A-4: Design, Synthesis, and Biological Evaluation In Vitro and In Vivo

Karetnikov,

Vasilyeva,

Babayeva

et al. 2024

ACS Pharmacol. Transl. Sci.

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A novel aromatic amide derivative SY-65 co-targeted tubulin and histone deacetylase 1 with potent anticancer activity in vitro and in vivo

Liu

et al. 2022

Biochemical Pharmacology

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Synthesis and biological evaluation of novel hybrids of phenylsulfonyl furoxan and phenstatin derivatives as potent anti-tumor agents

Huang

Wang

et al. 2022

European Journal of Medicinal Chemistry

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Novel diaryl-2H-azirines: Antitumor hybrids for dual-targeting tubulin and DNA

Cited by 11 publications

References 38 publications

3,4-Diarylisoxazoles─Analogues of Combretastatin A-4: Design, Synthesis, and Biological Evaluation In Vitro and In Vivo

3,4-Diarylisoxazoles─Analogues of Combretastatin A-4: Design, Synthesis, and Biological Evaluation In Vitro and In Vivo

A novel aromatic amide derivative SY-65 co-targeted tubulin and histone deacetylase 1 with potent anticancer activity in vitro and in vivo

Synthesis and biological evaluation of novel hybrids of phenylsulfonyl furoxan and phenstatin derivatives as potent anti-tumor agents

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