Design, synthesis and anticancer activity of trifluoromethylphenylamino substituted spiroindoles

Budovská, Mariana; Baláž, Matěj; Mezencev, Roman; Tischlerová, Viera; Zigová, Martina; Mojžiš, Ján

doi:10.1016/j.jfluchem.2018.09.011

Cited by 15 publications

(6 citation statements)

References 26 publications

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“…The majority of indole phytoalexins and their synthetic derivatives exhibit chirality [26,85]. Studies have demonstrated that chemically modifying the structure of indole phytoalexins results in increased antiproliferative activities compared to the original natural compounds [15,[86][87][88][89][90].…”

Section: Antiproliferative Effects Of Synthetic Analogues Of Indole P...mentioning

confidence: 99%

Anticancer Potential of Indole Phytoalexins and Their Analogues

Zigová,

Michalková,

Mojžiš

2024

Molecules

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Indole phytoalexins, found in economically significant Cruciferae family plants, are synthesized in response to pathogen attacks or stress, serving as crucial components of plant defense mechanisms against bacterial and fungal infections. Furthermore, recent research indicates that these compounds hold promise for improving human health, particularly in terms of potential anticancer effects that have been observed in various studies. Since our last comprehensive overview in 2016 focusing on the antiproliferative effects of these substances, brassinin and camalexin have been the most extensively studied. This review analyses the multifaceted pharmacological effects of brassinin and camalexin, highlighting their anticancer potential. In this article, we also provide an overview of the antiproliferative activity of new synthetic analogs of indole phytoalexins, which were synthesized and tested at our university with the aim of enhancing efficacy compared to the parent compound.

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Section: Antiproliferative Effects Of Synthetic Analogues Of Indole P...mentioning

confidence: 99%

Anticancer Potential of Indole Phytoalexins and Their Analogues

Zigová,

Michalková,

Mojžiš

2024

Molecules

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“…All prepared 2´-aminoanalogues trans-(±)-23a-29a and cis-(±)-23b-29b are more potent on all cell lines than 5-bromo-1methoxyspirobrassinol methyl ether and 5-bromo-1-Boc-spirobrassinol methyl ether trans-(±)-44a-45a and cis-(±)-44b-45b. The corresponding non-brominated 2´-aminoanalogues of 1methoxyspirobrassinol methyl ether and 1-Boc-spirobrassinol methyl ether were more active again (see reference 25,26). 4).…”

Section: Trans-(±)-37a-40a and Cis-(±)-37b-40b In Yields 20%-27% In All Cases Trans-(±)-cis-(±)mentioning

confidence: 99%

“…1-Boc substituted derivative of brassinin (Type I, Fig. 1) and thiourea derivatives of brassinins (Type III) display higher potencies of antiproliferative activity than the lead compounds 1 and 2 [25][26][27]. Homobrassinin (Type II) is more active than brassinin (1) and has been shown to cause ROS dependent apoptosis in Caco-2 colorectal cancer cells [28].…”

Section: Introductionmentioning

confidence: 99%

“…Likewise, the introduction of a substituted phenyl amino group to the compounds 3 and 4 (Type V) resulted in enhanced antiproliferative effect against human cancer cell lines [27,29]. Structural modification of phytoalexin (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether [(2R,3R)-(-)-6a] -synthetic 2-aminoanalogues (Type VII), 2'-aminoanalogues (Type VIII) or 2,2'diaminoanalogues (Type IX) exhibited remarkable anticancer activity [25,26,[29][30][31][32]. Synthetic analogues of cyclobrassinin (Type XI, Fig.…”

Section: Introductionmentioning

confidence: 99%

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Design, synthesis and biological evaluation of novel 5-bromo derivatives of indole phytoalexins

Budovská

Selešová

Tischlerová

et al. 2020

Preprint

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The increasing diversity of small molecule libraries is a major source for the discovery of new drug candidates. In term of this trend, we report the synthesis five series 5-bromosubstituted derivatives of indole phytoalexins Type A-E using straightforward synthetic approach. Novel compounds were screened in vitro for antiproliferative/cytotoxic activity against seven human cancer cell lines by MTT assay. Evaluation of their antiproliferative potency showed that the activity of some analogues was better or comparable to that of cisplatin and at the same time the toxicity of these compounds on 3T3 cells was lower than that of cisplatin. We found that all 5-bromosubstituted analogues of indole phytoalexins Type A-E exhibited lower or approximately the same activities as a previously studied corrensponding non-brominated compounds.

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“…On the other hand, spiroindoles, now wish to report the synthesis of some asymmetrical spiroheterobicyclic systems [19] [20] [21] [22]. Interestingly, spiroindoles had significant biological activities such as antiproliferative [23], antibacterial, antifungal [24], anti-inflammatory, fungistatic, bacteriostatic, and anticonvulsant [25] [26]. Based on these observations, the present work tends to obtain novel spiro[indole-thiazolidinones] derived from 5-substituted isatins, sulfanilamide, and thioglycolic acid because of their antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characteristic and Antimicrobial Activity of Some New Spiro[indol-thiazolidon-2,4-diones] and Bis(5-fluorospiro[indoline-3,2’-thiazolidine]-2,4’-dione) Probes

Al-Romaizan¹

2020

IJOC

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In a search for new antimicrobial agents, some new spiro[indol-thiazolidon-2,4-diones] (6a-c) were synthesized by condensation of 5-substituted isatins 1 with sulfanilamide in MeOH, followed by aroylation with p-nitrobenzoyl chloride in DMF to get compounds 4a-c. Cycloaddition of 4a-c with thioglycolic acid in a dry non-polar solvent (dioxane) gave the targets 6a-c. Also, bis(5-fluorospiro[indoline-3,2'-thiazolidine]-2,4'-dione) (9) was synthesized by condensation of 5-fluoroindoline-2,3-dione with benzene-1,4-diamine (2:1 by mol) in MeOH, which followed by cycloaddition with thioglycolic acid in dioxane gave compound 8. Acylation of the later with 2,2,2-trifluoroacetic anhydride in THF has yielded the target 9. Structures of the products have been deduced from their elemental analysis and spectral data. The in vitro antimicrobial activity of the new systems 6a-c, and 9 was tested.

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Design, synthesis and anticancer activity of trifluoromethylphenylamino substituted spiroindoles

Cited by 15 publications

References 26 publications

Anticancer Potential of Indole Phytoalexins and Their Analogues

Anticancer Potential of Indole Phytoalexins and Their Analogues

Design, synthesis and biological evaluation of novel 5-bromo derivatives of indole phytoalexins

Synthesis, Characteristic and Antimicrobial Activity of Some New Spiro[indol-thiazolidon-2,4-diones] and Bis(5-fluorospiro[indoline-3,2’-thiazolidine]-2,4’-dione) Probes

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