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

HAVRÁNKOVÁ, Eva, Jozef CSOLLEI and 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. Available from: https://dx.doi.org/10.3390/ecsoc-20-a055.

Basic information

• Original name: SYNTHESIS OF NOVEL 1,3,5-TRIAZINE DERIVATIVES AS POTENTIAL INHIBITORS OF TUMOR-ASSOCIATED CARBONIC ANHYDRASE IX
• Authors: HAVRÁNKOVÁ, Eva (203 Czech Republic, guarantor, belonging to the institution), Jozef CSOLLEI and Pavel PAZDERA (203 Czech Republic, belonging to the institution).
• Edition: 20TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY (ECSOC), 2016.

Other information

• Original language: English
• Type of outcome: Conference abstract
• Field of Study: 10401 Organic chemistry
• Country of publisher: Switzerland
• Confidentiality degree: is not subject to a state or trade secret
• WWW: URL
• RIV identification code: RIV/00216224:14310/16:00113676
• Organization unit: Faculty of Science
• Doi: http://dx.doi.org/10.3390/ecsoc-20-a055
• UT WoS: 000454430900120
• Keywords in English: s-Triazine; Supported Cu(I) cations; Piperazine; Aminobenzenesulfonamide; Aminoalcohole
• Tags: rivok
• Tags: International impact, Reviewed

Abstract

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.