SYNTHESIS OF NOVEL 1,3,5-TRIAZINE DERIVATIVES AS POTENTIAL
INHIBITORS OF TUMOR-ASSOCIATED CARBONIC ANHYDRASE IX

a 2016

SYNTHESIS OF NOVEL 1,3,5-TRIAZINE DERIVATIVES AS POTENTIAL INHIBITORS OF TUMOR-ASSOCIATED CARBONIC ANHYDRASE IX

HAVRÁNKOVÁ, Eva; Jozef CSOLLEI a Pavel PAZDERA

Základní údaje

Originální název

SYNTHESIS OF NOVEL 1,3,5-TRIAZINE DERIVATIVES AS POTENTIAL INHIBITORS OF TUMOR-ASSOCIATED CARBONIC ANHYDRASE IX

Autoři

HAVRÁNKOVÁ, Eva ; Jozef CSOLLEI a Pavel PAZDERA

Vydání

20TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY (ECSOC), 2016

Další údaje

Jazyk

angličtina

Typ výsledku

Konferenční abstrakt

Obor

10401 Organic chemistry

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/16:00113676

Organizační jednotka

Přírodovědecká fakulta

DOI

https://doi.org/10.3390/ecsoc-20-a055

UT WoS

000454430900120

Klíčová slova anglicky

s-Triazine; Supported Cu(I) cations; Piperazine; Aminobenzenesulfonamide; Aminoalcohole

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 23. 4. 2020 17:15, Mgr. Marie Novosadová Šípková, DiS.

Anotace

V originále

In the last few years, the s-triazine structural motive, as the carrier of pharmacophores, becomes a subject of many research works. Derivatives of s-triazines exhibit a broad spectrum of biological activities, and currently are in the forefront of interest, especially due their anti-tuberculosis, anti-bacterial and anti-cancer properties. [1] As the target of our interest we chose 1,3,5-triazine derivatives with potential antitumor activity against isozyme carboanhydrase hCAIX (associated with tumor growth). We used forwarded Artificial Neuronal Networks for the prediction of the biological activity of these derivatives. [2, 3] Syntheses of novel 1,3,5-triazine derivatives starting from cyanuric chloride are shown below. Target structural motives are involved in the s-triazine skeleton via substitution of chlorine atoms by amino group in various aminobenzensulfonamides, piperazines, amino alcohols and further amino compounds. It was found that substitution of the chlorine atoms in cyanuric chloride can be carried out as C-N coupling catalyzed by Cu(I) supported on weakly acidic macroporous cation exchanger resin of polyacrylate type via the oxidative addition - heterolytic addition - reductive elimination processes. The reaction could proceeds as a one-pot/ one-step synthetic process that is carried out under temperature control. Very good and excellent yields were obtained with shorter reaction times in comparison with similar usual syntheses realized step by step. Synthetic procedures optimized by this way can be applied in the preparation of the further various s-triazine with respect to the chemical behaviour of the individual nucleophilic reagents.

Citovat

HAVRÁNKOVÁ, Eva; Jozef CSOLLEI a Pavel PAZDERA. SYNTHESIS OF NOVEL 1,3,5-TRIAZINE DERIVATIVES AS POTENTIAL INHIBITORS OF TUMOR-ASSOCIATED CARBONIC ANHYDRASE IX. In 20TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY (ECSOC). 2016. Dostupné z: https://doi.org/10.3390/ecsoc-20-a055.

@proceedings{1646802,
   author = {Havránková, Eva and Csollei, Jozef and Pazdera, Pavel},
   booktitle = {20TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY (ECSOC)},
   doi = {https://doi.org/10.3390/ecsoc-20-a055},
   keywords = {s-Triazine; Supported Cu(I) cations; Piperazine; Aminobenzenesulfonamide; Aminoalcohole},
   language = {eng},
   title = {SYNTHESIS OF NOVEL 1,3,5-TRIAZINE DERIVATIVES AS POTENTIAL INHIBITORS OF TUMOR-ASSOCIATED CARBONIC ANHYDRASE IX},
   url = {https://sciforum.net/paper/view/conference/3646},
   year = {2016}
}

TY  - CONF
ID  - 1646802
AU  - Havránková, Eva - Csollei, Jozef - Pazdera, Pavel
PY  - 2016
TI  - SYNTHESIS OF NOVEL 1,3,5-TRIAZINE DERIVATIVES AS POTENTIAL INHIBITORS OF TUMOR-ASSOCIATED CARBONIC ANHYDRASE IX
KW  - s-Triazine
KW  - Supported Cu(I) cations
KW  - Piperazine
KW  - Aminobenzenesulfonamide
KW  - Aminoalcohole
UR  - https://sciforum.net/paper/view/conference/3646
L2  - https://sciforum.net/paper/view/conference/3646
N2  - In the last few years, the s-triazine structural motive, as the carrier of pharmacophores, becomes a subject of many research works. Derivatives of s-triazines exhibit a broad spectrum of biological activities, and currently are in the forefront of interest, especially due their anti-tuberculosis, anti-bacterial and anti-cancer properties. [1] As the target of our interest we chose 1,3,5-triazine derivatives with potential antitumor activity against isozyme carboanhydrase hCAIX (associated with tumor growth). We used forwarded Artificial Neuronal Networks for the prediction of the biological activity of these derivatives. [2, 3] Syntheses of novel 1,3,5-triazine derivatives starting from cyanuric chloride are shown below. Target structural motives are involved in the s-triazine skeleton via substitution of chlorine atoms by amino group in various aminobenzensulfonamides, piperazines, amino alcohols and further amino compounds. It was found that substitution of the chlorine atoms in cyanuric chloride can be carried out as C-N coupling catalyzed by Cu(I) supported on weakly acidic macroporous cation exchanger resin of polyacrylate type via the oxidative addition - heterolytic addition - reductive elimination processes. The reaction could proceeds as a one-pot/ one-step synthetic process that is carried out under temperature control. Very good and excellent yields were obtained with shorter reaction times in comparison with similar usual syntheses realized step by step. Synthetic procedures optimized by this way can be applied in the preparation of the further various s-triazine with respect to the chemical behaviour of the individual nucleophilic reagents.
ER  -

HAVRÁNKOVÁ, Eva; Jozef CSOLLEI a Pavel PAZDERA. SYNTHESIS OF NOVEL 1,3,5-TRIAZINE DERIVATIVES AS POTENTIAL INHIBITORS OF TUMOR-ASSOCIATED CARBONIC ANHYDRASE IX. In \textit{20TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY (ECSOC)}. 2016. Dostupné z: https://doi.org/10.3390/ecsoc-20-a055.

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