Synthesis and Antioxidant Activity of N′-(9H-Xanthen-9-yl)carbohydrazides

A series of new N′-(9H-xanthen-9-yl)carbohydrazides have been synthesized by the reaction of alkanehydrazides and cyclohexanecarbohydrazide with 9H-xanthen-9-ol (xanthydrol) and pyridinium per­chlorate. Xanthydrol and pyridinium perchlorate form a stable complex, N-(9H-xanthen-9-yl)pyridinium perchlorate, the lability of the C9–N+ bond in which favors easy introduction of the heterocyclic fragment into carbohydrazides. Antioxidant evaluation of the synthesized compounds revealed their antioxidant activity in the range of 0.62 to 0.73 relative units (with respect to ascorbic acid). Elongation of the alkyl chain of linear N′-(9H-xanthen-9-yl)alkanehydrazides increased their antioxidant activity, whereas branching of the alkyl fragment significantly reduced the antioxidant effect or did not affect it.

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Publication Details

Journal
Russian Journal of Organic Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1134/s1070428024602048
Primary Topic
Free Radicals and Antioxidants
Type
article
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article

Synthesis and Antioxidant Activity of N′-(9H-Xanthen-9-yl)carbohydrazides

Л. Г. Чеканова, V. Yu. Gorokhov, Svetlana A. Zabolotnykh, A. V. Kharitonova
Russian Journal of Organic Chemistry
Free Radicals and Antioxidants
article

Synthesis and Antioxidant Activity of N′-(9H-Xanthen-9-yl)carbohydrazides

Л. Г. Чеканова, V. Yu. Gorokhov, Svetlana A. Zabolotnykh, A. V. Kharitonova
article en

Abstract

A series of new N′-(9H-xanthen-9-yl)carbohydrazides have been synthesized by the reaction of alkanehydrazides and cyclohexanecarbohydrazide with 9H-xanthen-9-ol (xanthydrol) and pyridinium per­chlorate. Xanthydrol and pyridinium perchlorate form a stable complex, N-(9H-xanthen-9-yl)pyridinium perchlorate, the lability of the C9–N+ bond in which favors easy introduction of the heterocyclic fragment into carbohydrazides. Antioxidant evaluation of the synthesized compounds revealed their antioxidant activity in the range of 0.62 to 0.73 relative units (with respect to ascorbic acid). Elongation of the alkyl chain of linear N′-(9H-xanthen-9-yl)alkanehydrazides increased their antioxidant activity, whereas branching of the alkyl fragment significantly reduced the antioxidant effect or did not affect it.

Russian Journal of Organic ChemistryVol. 61(1)
Institute of Technical Chemistry (RU)
Openalex Percentile: Top 95%
Free Radicals and Antioxidants
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