One-Pot Synthesis of Aminodiperoxides from 1,5-Diketones, Geminal Bishydroperoxides and Ammonium Acetate

One-Pot Synthesis of Aminodiperoxides from 1,5-Diketones, Geminal Bishydroperoxides and Ammonium Acetate Full article

Journal

Molecules
ISSN: 1420-3049

Output data

Year: 2025, Volume: 30, Number: 24, Article number : 4703, Pages count : DOI: 10.3390/molecules30244703

Authors

Belyakova Yulia Yu. ¹ , Tsykunova Viktoria E. ¹ , Radulov Peter S. ¹ , Dzhemileva Lilya U. ¹ , Novikov Roman A. ¹ , Ilovaisky Alexey I. ^2,1 , Yaremenko Ivan A. ¹ , Terent’ev Alexander O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., 119991 Moscow, Russia
2	All-Russian Research Institute for Phytopathology, 5 Institute Street, Odintsovo District, 143050 B. Vyazyomy, Moscow Region, Russia

Herein, we report an efficient one-pot synthesis of bridged aminodiperoxides via a three-component reaction of 1,5-diketones with geminal bishydroperoxides and ammonium acetate. The synthesized aminodiperoxides are stable despite containing an unprotected secondary NH-group adjacent to two peroxide functionalities. Under optimal conditions, the reaction affords aminodiperoxides in high yields (up to 88%) with outstanding selectivity and high atom economy, thereby eliminating the need for column chromatographic purification. The synthesized aminodiperoxides exhibit potent cytotoxicity and remarkable selectivity toward Jurkat, K562, and A549 cancer cell lines, and are significantly superior to the clinically used anticancer agent camptothecin. Among all tested compounds, 3ec is the most promising candidate, exhibiting high activity and selectivity toward all tested cell lines (Jurkat: CC50 = 12.9 µM, SI = 67.09; K562: CC50 = 19.6 µM, SI = 44.28; A549: CC50 = 48.2 µM, SI = 17.98). Furthermore, a novel class of fungicidal compounds has been discovered. The aminodiperoxides exhibit fungicidal activity against phytopathogenic fungi, in some cases comparable to the commercial fungicide Triadimefon.

Belyakova Y.Y. , Tsykunova V.E. , Radulov P.S. , Dzhemileva L.U. , Novikov R.A. , Ilovaisky A.I. , Yaremenko I.A. , Terent’ev A.O.
One-Pot Synthesis of Aminodiperoxides from 1,5-Diketones, Geminal Bishydroperoxides and Ammonium Acetate
Molecules. 2025. V.30. N24. 4703 . DOI: 10.3390/molecules30244703 OpenAlex

OpenAlex:

W4417123670

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