ArticleMolecules (Basel, Switzerland)2020
Glycoconjugation of Betulin Derivatives Using Copper-Catalyzed 1,3-Dipolar Azido-Alkyne Cycloaddition Reaction and a Preliminary Assay of Cytotoxicity of the Obtained Compounds.
Article in Molecules (Basel, Switzerland), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 28 citations in OpenAlex.
- N2-substituted triazoles as trypanothione reductase inhibitors: in silico evaluation, synthesis, and anti-leishmanial activity.Journal of computer-aided molecular design · 2026Article
- Novel C3/C28-bis-1,2,4-Triazolyl-sulfanylacetate-betulin Derivatives: Synthesis and Evaluation of Anticancer Potential.International journal of molecular sciences · 2026Article
- Betulin-Amino Acid Molecular Hybrids: Synthesis, Structure and Pharmacological Potential.International journal of molecular sciences · 2026Article
- New Synthetic Approach to C‑30 Ethers, Esters, and Amines of Betulin Using the Mitsunobu Reaction and Biological Evaluation of the Products.ACS omega · 2026Article
- Article
- 1,3-Dipolar Cycloaddition and Mannich Reactions of Alkynyl Triterpenes: New Trends in Synthetic Strategies and Pharmacological Applications.International journal of molecular sciences · 2025Review
- New Difunctional Derivatives of Betulin: Preparation, Characterization and Antiproliferative Potential.Molecules (Basel, Switzerland) · 2025Article
- Assessment of the Lipophilicity of Indole Derivatives of Betulin and Their Toxicity in a Zebrafish Model.Molecules (Basel, Switzerland) · 2024Article
- Drug Delivery Systems of Betulin and Its Derivatives: An Overview.Biomedicines · 2024Review
- Synthesis, Pharmacological Properties, and Potential Molecular Mechanisms of Antitumor Activity of Betulin and Its Derivatives in Gastrointestinal Cancers.Pharmaceutics · 2023Review
- A Small Sugar Molecule with Huge Potential in Targeted Cancer Therapy.Pharmaceutics · 2023Review
- Semisynthetic Derivatives of Pentacyclic Triterpenes Bearing Heterocyclic Moieties with Therapeutic Potential.Molecules (Basel, Switzerland) · 2022Review
- Design, Synthesis and Preliminary Evaluation of the Cytotoxicity and Antibacterial Activity of Novel Triphenylphosphonium Derivatives of Betulin.Molecules (Basel, Switzerland) · 2022Article
- Design and Synthesis of Novel Betulin Derivatives Containing Thio-/Semicarbazone Moieties as Apoptotic Inducers through Mitochindria-Related Pathways.Molecules (Basel, Switzerland) · 2021Article
- Are Ancestral Medical Practices the Future Solution to Today's Medical Problems?Molecules (Basel, Switzerland) · 2021Article
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
Pentacyclic lupane-type triterpenoids, such as betulin and its synthetic derivatives, display a broad spectrum of biological activity. However, one of the major drawbacks of these compounds as potential therapeutic agents is their high hydrophobicity and low bioavailability. On the other hand, the presence of easily transformable functional groups in the parent structure makes betulin have a high synthetic potential and the ability to form different derivatives. In this context, research on the synthesis of new betulin derivatives as conjugates of naturally occurring triterpenoid with a monosaccharide via a linker containing a heteroaromatic 1,2,3-triazole ring was presented. It has been shown that copper-catalyzed 1,3-dipolar azide-alkyne cycloaddition reaction (CuAAC) provides an easy and effective way to synthesize new molecular hybrids based on natural products. The chemical structures of the obtained betulin glycoconjugates were confirmed by spectroscopic analysis. Cytotoxicity of the obtained compounds was evaluated on a human breast adenocarcinoma cell line (MCF-7) and colorectal carcinoma cell line (HCT 116). The obtained results show that despite the fact that the obtained betulin glycoconjugates do not show interesting antitumor activity, the idea of adding a sugar unit to the betulin backbone may, after some modifications, turn out to be correct and allow for the targeted transport of betulin glycoconjugates into the tumor cells.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.