Synthesis and antibacterial activity of betulonic acid amides with piperazine derivatives

Chue, Kuck-Tack; Chang, Mingqin; Ten, Leonid N.

doi:10.1007/s10600-011-0051-x

Cited by 8 publications

(2 citation statements)

References 18 publications

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“…Asi nejvýznamnějším příkladem patogenní bakterie může být grampozitivní bakterie Staphylococcus aureus 27 . Podle publikovaných údajů 28 triterpenoidy vykazují antimikrobiální aktivitu proti Staphylococcus aureus, Escherichia coli a Enterococcus faecalis v koncentracích mezi 0,006-200 mg ml -1 . U betulonové…”

Section: Biologické Aktivityunclassified

Betulonic and Platanic Acids as a Basis for the Synthesis of New Therapeutically Effective Substances

Černá,

Wimmer,

Massyagutova

et al. 2024

Chem. Listy

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Natural substances produced by plants represent an important source of new medicinal products. This article is focused on the description of the antimicrobial, antiviral, and cytotoxic activity of the synthesized derivatives of betulonic and platanic acids, especially their oxime-based derivatives. It is also aimed at providing overview of the possible use of these derivatives in the treatment of infectious or cancer diseases.

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Section: Biologické Aktivityunclassified

Betulonic and Platanic Acids as a Basis for the Synthesis of New Therapeutically Effective Substances

Černá,

Wimmer,

Massyagutova

et al. 2024

Chem. Listy

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“…The conducted studies have shown that these compounds have antiproliferative activity against a range of human cancer lines (MT-4, MOLT-4, CEM, Hep G2, Bel-7402, HeLa, MCF-7, Bcap-37, MGc-803, PC3 and A375; Figure 1) [10][11][12]. Moreover, amide and ester derivatives of betulonic acid have been found to possess antiviral, anti-inflammatory and antibacterial properties (Figure 1) [13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Pharmacokinetic Profile, Anticancer Activity and Toxicity of the New Amides of Betulonic Acid—In Silico and In Vitro Study

Bębenek,

Rzepka,

Hermanowicz

et al. 2024

IJMS

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Betulonic acid (B(O)A) is a pentacyclic lupane-type triterpenoid that widely exists in plants. There are scientific reports indicating anticancer activity of B(O)A, as well as the amides and esters of this triterpenoid. In the first step of the study, the synthesis of novel amide derivatives of B(O)A containing an acetylenic moiety was developed. Subsequently, the medium-soluble compounds (EB171 and EB173) and the parent compound, i.e., B(O)A, were investigated for potential cytotoxic activity against breast cancer (MCF-7 and MDA-MB-231) and melanoma (C32, COLO 829 and A375) cell lines, as well as normal human fibroblasts. Screening analysis using the WST-1 test was applied. Moreover, the lipophilicity and ADME parameters of the obtained derivatives were determined using experimental and in silico methods. The toxicity assay using zebrafish embryos and larvae was also performed. The study showed that the compound EB171 exhibited a significant cytotoxic effect on cancer cell lines: MCF-7, A-375 and COLO 829, while it did not affect the survival of normal cells. Moreover, studies on embryos and larvae showed no toxicity of EB171 in an animal model. Compared to EB171, the compound EB173 had a weaker effect on all tested cancer cell lines and produced less desirable effects against normal cells. The results of the WST-1 assay obtained for B(O)A revealed its strong cytotoxic activity on the examined cancer cell lines, but also on normal cells. In conclusion, this article describes new derivatives of betulonic acid—from synthesis to biological properties. The results allowed to indicate a promising direction for the functionalization of B(O)A to obtain derivatives with selective anticancer activity and low toxicity.

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Synthesis and Cytotoxicity of Lupane Mono- and Bis-Piperazinylamides

Giniyatullina

Казакова

2021

Chem Nat Compd

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Synthesis and antibacterial activity of betulonic acid amides with piperazine derivatives

Cited by 8 publications

References 18 publications

Betulonic and Platanic Acids as a Basis for the Synthesis of New Therapeutically Effective Substances

Betulonic and Platanic Acids as a Basis for the Synthesis of New Therapeutically Effective Substances

Synthesis, Pharmacokinetic Profile, Anticancer Activity and Toxicity of the New Amides of Betulonic Acid—In Silico and In Vitro Study

Synthesis and Cytotoxicity of Lupane Mono- and Bis-Piperazinylamides

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