Synthesis and cellular effects of novel 1,3,5-triazine derivatives in DLD and Ht-29 human colon cancer cell lines

Wróbel, Agnieszka; Kolesińska, Beata; Frączyk, Justyna; Kamiński, Zbigniew J.; Tankiewicz-Kwedlo, Anna; Hermanowicz, Justyna Magdalena; Czarnomysy, Robert; Maliszewski, Dawid; Drozdowska, Danuta

doi:10.1007/s10637-019-00838-9

Cited by 10 publications

(8 citation statements)

References 27 publications

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“…Preliminary work support its versatility in the synthesis of pharmaceutically active compounds. [14][15][16] While other potential applications include use as new chiral auxiliaries 17 building blocks, and pesticides 18 etc.…”

Section: Discussionmentioning

confidence: 99%

Reactions of quinine with 2-chloro-4,6-dimethoxy-1,3,5-triazine

Sukiennik¹,

Kasperowicz-Frankowska²,

Szczesio³

et al. 2020

Arkivoc

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Quinine reacts with 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) via a multistage process leading to destruction of the quinuclidine fragment and attachment of two triazinyl substituents. In the first, reversible stage, CDMT reacts with the aromatic nitrogen of the quinoline, followed by the slow migration of triazine moiety on the bridgehead nitrogen atom of quinuclidine. The bicyclic system, after quaternization with CDMT, was opened by privileged attack of nucleophilic chloride on methylene carbon in the bridge substituted with vinyl group. In the final stage the second 4,6-dimethoxy-1,3,5-triazin-2-yl moiety was attached to the hydroxy group. The product structure was confirmed by X-ray crystallographic measurements, MS, 1 H and 13 C NMR, and IR spectroscopy.

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Section: Discussionmentioning

confidence: 99%

Reactions of quinine with 2-chloro-4,6-dimethoxy-1,3,5-triazine

Sukiennik¹,

Kasperowicz-Frankowska²,

Szczesio³

et al. 2020

Arkivoc

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“…Compound 30 (Figure 9) obtained via the click chemistry method showed higher potency than doxorubicin. Derivative 30 exhibited an IC50 against MCF-7 and HepG2 cells of 2.95 µg/mL and 3.70 µg/mL, respectively, and showed no toxic activity against the growth of normal HFB4 cells [33].…”

Section: Primary Anticancer Studiesmentioning

confidence: 99%

“…5-fluorouracil exhibited lower activity as a reference. Compound 58 increased the expression of BAX and decreased the amount of Bcl-2 both in DLD-1 and in HT-29 [33]. Screening studies of 2-(dichloromethyl)pyrazolo[1,5-a][1,3,5]triazines 62-66 (Figure 13) showed potential anticancer properties against non-small cell lung cancers, colon cancers, renal cancer, etc.…”

Section: Primary Anticancer Studiesmentioning

confidence: 99%

Recent Advances in the Biological Activity of s-Triazine Core Compounds

Maliszewski

Drozdowska

2022

Pharmaceuticals

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An effective strategy for successful chemotherapy relies on creating compounds with high selectivity against cancer cells compared to normal cells and relatively low cytotoxicity. One such approach is the discovery of critical points in cancer cells, i.e., where specific enzymes that are potential therapeutic targets are generated. Triazine is a six-membered heterocyclic ring compound with three nitrogen replacing carbon-hydrogen units in the benzene ring structure. The subject of this review is the symmetrical 1,3,5-triazine, known as s-triazine. 1,3,5-triazine is one of the oldest heterocyclic compounds available. Because of its low cost and high availability, it has attracted researcher attention for novel synthesis. s-Triazine has a weak base, it has much weaker resonance energy than benzene, therefore, nucleophilic substitution is preferred to electrophilic substitution. Heterocyclic bearing a symmetrical s-triazine core represents an interesting class of compounds possessing a wide spectrum of biological properties such as anti-cancer, antiviral, fungicidal, insecticidal, bactericidal, herbicidal and antimicrobial, antimalarial agents. They also have applications as dyes, lubricants, and analytical reagents. Hence, the group of 1,3,5-triazine derivatives has developed over the years. Triazine is not only the core amongst them, but is also a factor increasing the kinetic potential of the entire derivatives. Modifying the structure and introducing new substituents makes it possible to obtain compounds with broad inhibitory activity on processes such as proliferation. In some cases, s-triazine derivatives induce cell apoptosis. In this review we will present currently investigated 1,3,5-triazine derivatives with anti-cancer activities, with particular emphasis on their inhibition of enzymes involved in the process of tumorigenesis.

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“…Further appending of hybrid triazine‐nitrogen mustards with amino acids and peptides generated highly potent anticancer hybrids 38 a‐o, 39, 40 and 41 ; Figure 8. These hybrids induced dose‐ and time‐dependent cytotoxicity in the cell lines MCF‐7, DLD‐1, MDA‐MB‐231, and HT‐29 and trigger apoptosis by weakening of intracellular signaling pathways (Fraczyk et al, 2016; Wrobel et al, 2019).…”

Section: Anticancer Properties Of Hybrid Molecules Based On 135‐trimentioning

confidence: 99%

Hybrid molecules based on 1,3,5‐triazine as potential therapeutics: A focused review

Prasher

Sharma

Aljabali

et al. 2020

Drug Development Research

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Majority of the representative drugs customarily interact with multiple targets manifesting unintended side effects. In addition, drug resistance and over expression of the cellular efflux‐pumps render certain classes of drugs ineffective. With only a few innovative formulations in development, it is necessary to identify pharmacophores and novel strategies for creating new drugs. The conjugation of dissimilar pharmacophoric moieties to design hybrid molecules with an attractive therapeutic profile is an emerging paradigm in the contemporary drug development regime. The recent decade witnessed the remarkable biological potential of 1,3,5‐triazine framework in the development of various chemotherapeutics. The appending of the 1,3,5‐triazine nucleus to biologically relevant moieties has delivered exciting results. The present review focuses on 1,3,5‐triazine based hybrid molecules in the development of pharmaceuticals.

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Synthesis and cellular effects of novel 1,3,5-triazine derivatives in DLD and Ht-29 human colon cancer cell lines

Cited by 10 publications

References 27 publications

Reactions of quinine with 2-chloro-4,6-dimethoxy-1,3,5-triazine

Reactions of quinine with 2-chloro-4,6-dimethoxy-1,3,5-triazine

Recent Advances in the Biological Activity of s-Triazine Core Compounds

Hybrid molecules based on 1,3,5‐triazine as potential therapeutics: A focused review

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