Синтез 7-арил-6,7-дигідротетразоло[1,5-a]піримідин-5(4H)-онів

• Date: 2014
• Main Authors: Svitlichna, N. V., Borodina, V. V., Lipson, V. V., Musatov, V. I.
• Format: Article
• Language: Ukrainian
• Published: National University of Pharmacy 2014
• Subjects: 1Н-тетразол-5-амін; 1; 3-карбонільні біелектрофіли; метилцинамати; арилметиліденмалонові кислоти; арилметиліденпохідні 2; 2-диметил-1; 3-діоксан-4; 6-діону; кислота Мельдрума; 6; 7-дигідро-7-арилтетразоло[1; 5-a]піримідин-5(4H)-они; синтез; фармакологічна актив; УДК 547.796.1
• Online Access: https://ophcj.nuph.edu.ua/article/view/ophcj.14.785
• Journal Title: Journal of Organic and Pharmaceutical Chemistry

Arylmethyliden derivatives of 2,2-dimethyl-1,3-dioxane-4,6-dione; Meldrum`s acid; 6,7-dihydro-7-aryltetrazolo [1,5-a]pyrimidin-5(4H)-ones; synthesis; pharmacological activityCyclocondensations of 1H-tetrazol-5-amine with methylcinnamates, arylmethyliden malonic acids and arylmethyliden derivatives of 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum`s acid) proceed regioselectively and lead to formation of 7-aryl-6,7-dyhidrotetrazolo[1,5-a]pyrimidin-5(4H)-ones. The direction of cyclization corresponds to the interaction of the carbon atom in β-position of the unsaturated carbonyl compounds with the endocyclic nitrogen atom and the carbonyl group with amino group in the aminoazole molecule. Compounds of the isomeric structure in any of the experiments have been not identified. The structures and composition of the newly synthesized tetrazolo[1,5-a]pyrimidin-5(4H)-ones have been confirmed by elemental analysis, infrared spectroscopy (IR), nuclear magnetic resonance on protones (1H NMR) and mass spectra data. Virtual screening of 7-aryl-6,7-dihydrotetrazolo[1,5-a]pyrimidin-5(4H)-ones carried out using the PASS programme for 780 types of the pharmacological action has demonstrated that it is expedient to test these compounds by their analgesic and anti-inflammatory activity, as well as as potential agents for the treatment of heart failure.