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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F16%3A00113676" target="_blank" >RIV/00216224:14310/16:00113676 - isvavai.cz</a>

Výsledek na webu

<a href="https://sciforum.net/paper/view/conference/3646" target="_blank" >https://sciforum.net/paper/view/conference/3646</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/ecsoc-20-a055" target="_blank" >10.3390/ecsoc-20-a055</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

O - Ostatní výsledky

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů