Development of New Amide Derivatives of Betulinic Acid: Synthetic Approaches and Structural Characterization

In this study, we report the synthesis of three new derivatives of betulinic acid, a pentacyclic triterpenoid known for its antitumor activity. These derivatives were synthesized via amide bond formation at the C-28 position using 3-[(Ethylimino)methylidene]amino-N,N-dimethylpropan-1-amine (EDC)/Hydroxybenzotriazole (HOBt) activation and various amines as nucleophiles. The synthesized compounds were characterized by nuclear magnetic resonance (NMR) techniques, including proton (1H), carbon-13 (13C), COSY, HSQC, and DEPT, as well as ultraviolet–visible (UV-VIS) spectroscopy, Fourier-transform infrared (IR) and elemental analysis. This work highlights the potential of semi-synthetic modification of betulinic acid to enhance anticancer properties while addressing challenges in solubility and bioavailability. Further structural optimization and formulation studies are warranted to improve drug-like properties and therapeutic applicability.

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Publication Details

Journal
Molbank
Published
2025-10-13
DOI
https://doi.org/10.3390/m2072
Citations
2
Primary Topic
Natural product bioactivities and synthesis
Type
article
Field-Weighted Citation Impact
1.61
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article

Development of New Amide Derivatives of Betulinic Acid: Synthetic Approaches and Structural Characterization

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2 citations
Molbank
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article

Development of New Amide Derivatives of Betulinic Acid: Synthetic Approaches and Structural Characterization

Zimo Ren, Paolo Coghi, Carmine Coluccini, Yuhan Xie, Jin Qi, Qinwei Xu
article en
2 citations

Abstract

In this study, we report the synthesis of three new derivatives of betulinic acid, a pentacyclic triterpenoid known for its antitumor activity. These derivatives were synthesized via amide bond formation at the C-28 position using 3-[(Ethylimino)methylidene]amino-N,N-dimethylpropan-1-amine (EDC)/Hydroxybenzotriazole (HOBt) activation and various amines as nucleophiles. The synthesized compounds were characterized by nuclear magnetic resonance (NMR) techniques, including proton (1H), carbon-13 (13C), COSY, HSQC, and DEPT, as well as ultraviolet–visible (UV-VIS) spectroscopy, Fourier-transform infrared (IR) and elemental analysis. This work highlights the potential of semi-synthetic modification of betulinic acid to enhance anticancer properties while addressing challenges in solubility and bioavailability. Further structural optimization and formulation studies are warranted to improve drug-like properties and therapeutic applicability.

MolbankVol. 2025(4)
Macau University of Science and Technology (MO), China Medical University (TW)
Openalex Percentile: Top 14%
Natural product bioactivities and synthesis
1.61
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