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Synthesis and Antioxidant Activity of New N-Containing Hybrid Derivatives of Gallic and Ursolic Acids

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Chemistry of Natural Compounds Aims and scope

New hybrid derivatives of ursolic and gallic acids linked through an ethylene linker and containing hydrazide and 1,3,4-oxadiazol-2-thione as terminal substituents were synthesized. Hydrazinolysis of methyl 3-(3β-acetoxyurs-12-en-28-oyloxy)-4,5-dihydroxybenzoate led to cleavage at the triterpenoid C-28-ester bond to produce (3β-acetoxyurs-12-en)-28-oyl hydrazide and methyl gallate. The dioxolane protecting group on the polyphenol moiety was easily removed with retention of the ester on the aromatic moiety during the reaction of hydrazine with methyl 3-(3β-acetoxyurs-12-en-28-oyloxy)-4,5-[(R,S)-methoxymethylenedioxy]benzoate. The new hybrid derivatives of ursolic and gallic acids containing hydrazide and 1,3,4-oxadiazole moieties possessed high antioxidant activity.

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Acknowledgment

The work was performed in the framework of Project ERA.Net RUS Plus No. RUS_ST2017-139 AnticancerBet (financial support from RFBR Project 18-53-76001), Federal Programs AAAA-A21-121011490016-8 and AAAA-A21-121011490015-1, and Grant 32101472 from the Chinese National Natural Sciences Foundation. We thank the Chemical Research Center for Common Use, SB, RAS, for spectral and analytical measurements.

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Authors and Affiliations

  1. Novosibirsk Institute of Organic Chemistry, 9 Prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russia

    S. A. Popov & E. E. Shul’ts

  2. Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, 210042, Nanjing, P. R. China

    C. Wang & Z. Qi

  3. Riga Technical University, 3 P. Valdena St, Riga, LV-1048, Latvia

    M. Turks

Authors
  1. S. A. Popov
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  2. C. Wang
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  3. Z. Qi
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  4. E. E. Shul’ts
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  5. M. Turks
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Corresponding author

Correspondence to S. A. Popov.

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Translated from Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2021, pp. 893–897.

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Popov, S.A., Wang, C., Qi, Z. et al. Synthesis and Antioxidant Activity of New N-Containing Hybrid Derivatives of Gallic and Ursolic Acids. Chem Nat Compd 57, 1042–1046 (2021). https://doi.org/10.1007/s10600-021-03546-0

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  • DOI: https://doi.org/10.1007/s10600-021-03546-0

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