A comparative evaluation of monomethoxy substituted o-diarylazoles as antiproliferative microtubule destabilizing agents

Silyanova, Eugenia A.; Ushkarov, Vladimir I.; Samet, A. V.; Maksimenko, Anna S.; Koblov, Ivan A.; Кислый, В. П.; Semenova, Marina N.; Семенов, В. В.

doi:10.1016/j.mencom.2022.01.039

Cited by 10 publications

(6 citation statements)

References 22 publications

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“…Silyanova and colleagues found that only the isoxazole heterocycle and the unsubstituted benzene ring next to the heteroatom conferred the appropriate conformation of the molecule to exert antiproliferative effects through the microtubule destabilization mode of action. The 4,5-diarylisoxazoles showed greater antimitotic activity than 3,4-diarylisoxazoles [ 35 ]. In 2018, isoxazole chalcone derivatives with structural similarities to CA4 were synthesized.…”

Section: Biological Effects Of Natural Products Containing the Isoxaz...mentioning

confidence: 99%

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

Wang

Tang

et al. 2023

Pharmaceuticals

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Isoxazoles and isoxazolines are five-membered heterocyclic molecules containing nitrogen and oxygen. Isoxazole and isoxazoline are the most popular heterocyclic compounds for developing novel drug candidates. Over 80 molecules with a broad range of bioactivities, including antitumor, antibacterial, anti-inflammatory, antidiabetic, cardiovascular, and other activities, were reviewed. A review of recent studies on the use of isoxazoles and isoxazolines moiety derivative activities for natural products is presented here, focusing on the parameters that affect the bioactivity of these compounds.

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Section: Biological Effects Of Natural Products Containing the Isoxaz...mentioning

confidence: 99%

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

Wang

Tang

et al. 2023

Pharmaceuticals

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“…A structure-activity relationship study revealed that isoxazoles 31 with an unsubstituted benzene ring at the C-3 of the isoxazole ring provide the appropriate configuration for the molecule to exhibit an antiproliferative effect by a microtubule destabilising mode of action. 78…”

Section: Selectivity Via Pyridinium Saltsmentioning

confidence: 99%

Primary nitro compounds: progress in the synthesis of isoxazoles by condensation with aldehydes or activated ketones

De Sarlo,

Machetti

2023

Org. Biomol. Chem.

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“…Consequently, 3,4-disubstituted isoxazoles had to be synthesized from nitrostilbenes in the Semenov group’s biological investigation (Scheme 1c ). 9c 11…”

Section: Table 1 Optimization Of Reaction Conditionsmentioning

confidence: 99%

Regioselective Synthesis of 3,4-Disubstituted Isoxazoles by Using a Chalcone-Rearrangement Strategy

Nakamura¹,

Kine²,

Uenishi³

et al. 2023

Synlett

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We developed a regioselective synthesis of 3,4-disubstituted isoxazoles using a chalcone rearrangement strategy. The reaction of β-ketoacetals with hydroxylamine hydrochloride and pyridine afforded the corresponding 3,4-disubstituted isoxazoles via isoxazolines or oximes. Depending on the substrate, another disubstituted isomer was also obtained under our optimized conditions, and the reaction mechanism for each transformation was proposed.

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A comparative evaluation of monomethoxy substituted o-diarylazoles as antiproliferative microtubule destabilizing agents

Cited by 10 publications

References 22 publications

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

Isoxazole/Isoxazoline Skeleton in the Structural Modification of Natural Products: A Review

Primary nitro compounds: progress in the synthesis of isoxazoles by condensation with aldehydes or activated ketones

Regioselective Synthesis of 3,4-Disubstituted Isoxazoles by Using a Chalcone-Rearrangement Strategy

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