Hederagenin amide derivatives as potential antiproliferative agents

Rodríguez-Hernández, Diego; Barbosa, Luiz C. A.; Demuner, Antônio J.; Martins, João Paulo Ataide; Fischer, Lucie; Csuk, René

doi:10.1016/j.ejmech.2019.02.057

Cited by 20 publications

(11 citation statements)

References 32 publications

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“…In general, the hydroxylated derivatives were less active than the acetylated derivatives. Among them, compound 28 (Figure 13) carrying a piperazinyl presented good cytotoxic activity against A2780 cells (EC 50 ¼ 1.9 mM), which was better than parent compound hederagenin (IC 50 > 30 mM) 52 .…”

Section: Biological Effects Of Natural Products Containing the Piperazinyl Moietymentioning

confidence: 99%

Piperazine skeleton in the structural modification of natural products: a review

Zhang

Guo

Deng

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Piperazine moiety is a cyclic molecule containing two nitrogen atoms in positions 1 and 4, as well as four carbon atoms. Piperazine is one of the most sought heterocyclics for the development of new drug candidates with a wide range of applications. Over 100 molecules with a broad range of bioactivities, including antitumor, antibacterial, anti-inflammatory, antioxidant, and other activities, were reviewed. This article reviewed investigations regarding piperazine groups for the modification of natural product derivatives in the last decade, highlighting parameters that affect their biological activity.

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Section: Biological Effects Of Natural Products Containing the Piperazinyl Moietymentioning

confidence: 99%

Piperazine skeleton in the structural modification of natural products: a review

Zhang

Guo

Deng

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Amide linkage holds irreplaceable roles in biological systems; at the same time, amide linkage is of wide appearance in modern pharmaceuticals and bioactive compounds, which are widely used in the fields including medicine, chemical industry, and so on. Therefore, amide derivatives have also attracted considerable attention because of their important bioactivities, including antitumor activity, antibacterial activity, antimelanogenic activity, antifungal activity, anticonvulsant activity, anti‐inflammatory activity, antitubercular activity, and brain‐penetrant inhibitory activity . Therefore, in this study, we designed and synthesized a series of indole derivatives containing the molecular scaffold of indole and amide moieties, and further evaluated their biological activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of novel indoleamide derivatives as antioxidative and antitumor agents

Zhang

Wang

et al. 2020

Journal of Heterocyclic Chem

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Novel indole amide derivatives C1‐C10 were successfully synthesized and characterized by 1H NMR, 13C NMR, IR, MS, and elemental analysis, and their molecular formulas were C14H10N6O, C13H10N4O, C16H13N3O2, C19H14N2O2, C16H11N3OS, C15H13N3O, C12H9N5O, C16H10ClN3OS, C15H17N3O2, and C13H14N2O3, respectively. The primary biological activities of these compounds were evaluated in vitro by the DPPH assay, H2O2‐induced oxidative stress injury assay, and cytotoxicity assay. The results indicated that compounds C1, C2, C4, C7, and C9 exhibited DPPH·scavenging ability, while C3, C4, C5, and C8 showed potent growth‐inhibitory activities against various human tumor cells, including MDA‐MB‐231, Hela, A549, and HT29. Interestingly, compound C4 showed potent scavenging effects on the DPPH radical and possessed protective effect on H2O2‐induced oxidative stress injury in human neuroblastoma SH‐SY5Y cells at low concentrations; however, C4 exhibited significant toxicity against four human tumor cells at a higher concentration in all treatments, and the range of IC50 value was 7.91 to 13.35 μM.

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“…Betulonic acid diethylentriamine conjugate showed partial activity against methicillin-resistant S. aureus and the fungi C. neoformans [265]. [265,275], 268 [281], 269 [265], 270, 271 [300], 272, 273, 290 [298], 275, 299 [299], 276 [294,303], 277 [258], 278 [259], 279 [260], 280 [295,299], 281, 292 [302], 282 [289], 283 [274], 284 [304], 285 [287], 286 [291], 287 [284], 288 [277], 289 [285], 291 [283], 293 [296], 294 [280], 295 [297], 296 [279], 297 [274].…”

Section: Terpene-and Triterpene-based Polyamine Derivativesmentioning

confidence: 99%

“…Conjugates of oleanolic acid with spermine 300 and 301 were studied for the characteristics of their oleanolic acid backbone that is a conformationally rigid and convenient chiral building block for preparing functional soft materials. However, besides their supramolecular characteristics, conjugates displayed high cytotoxicity with a range IC50 [265,275], 268 [281], 269 [265], 270, 271 [300], 272, 273, 290 [298], 275, 299 [299], 276 [294,303], 277 [258], 278 [259], 279 [260], 280 [295,299], 281, 292 [302], 282 [289], 283 [274], 284 [304], 285 [287], 286 [291], 287 [284], 288 [277], 289 [285], 291 [283], 293 [296], 294 [280], 295 [297], 296 [279], 297 [274].…”

Section: Terpene-and Triterpene-based Polyamine Derivativesmentioning

confidence: 99%

See 1 more Smart Citation

From Marine Metabolites to the Drugs of the Future: Squalamine, Trodusquemine, Their Steroid and Triterpene Analogues

Казакова

Giniyatullina

Babkov

et al. 2022

IJMS

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This review comprehensively describes the recent advances in the synthesis and pharmacological evaluation of steroid polyamines squalamine, trodusquemine, ceragenins, claramine, and their diverse analogs and derivatives, with a special focus on their complete synthesis from cholic acids, as well as an antibacterial and antiviral, neuroprotective, antiangiogenic, antitumor, antiobesity and weight-loss activity, antiatherogenic, regenerative, and anxiolytic properties. Trodusquemine is the most-studied small-molecule allosteric PTP1B inhibitor. The discovery of squalamine as the first representative of a previously unknown class of natural antibiotics of animal origin stimulated extensive research of terpenoids (especially triterpenoids) comprising polyamine fragments. During the last decade, this new class of biologically active semisynthetic natural product derivatives demonstrated the possibility to form supramolecular networks, which opens up many possibilities for the use of such structures for drug delivery systems in serum or other body fluids.

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Hederagenin amide derivatives as potential antiproliferative agents

Cited by 20 publications

References 32 publications

Piperazine skeleton in the structural modification of natural products: a review

Piperazine skeleton in the structural modification of natural products: a review

Synthesis and biological evaluation of novel indoleamide derivatives as antioxidative and antitumor agents

From Marine Metabolites to the Drugs of the Future: Squalamine, Trodusquemine, Their Steroid and Triterpene Analogues

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