A reação "click" na síntese de 1,2,3-triazóis: aspectos químicos e aplicações

Synthesis by Click Reactions and Antiplasmodial Activity of Lupeol 1,2,3-Triazole Derivatives

“…22 Its IR spectrum showed characteristic bands in These signals confirm the insertion of a propargyl group in the lupeol structure. 22 The spectrum of 13 displayed common signals with lupeol, 28,29 The CuAAC, often referred to as "click reaction", occurred between the terminal alkyne of the lupeol propargyl ether (13) and known organic azides [17][18][19]21 that were previously synthesized. 22 CuAAc is known for its high efficiency without need for special reaction conditions, such as high temperature and/or high pressure, and is regioselective giving only the 1,4-disubstituted isomer.…”

“…22 CuAAc is known for its high efficiency without need for special reaction conditions, such as high temperature and/or high pressure, and is regioselective giving only the 1,4-disubstituted isomer. [17][18][19] The conditions of the click reactions used to prepare 14a-e (24 hours of reaction, dichloromethane and water as solvents) were similar to those previously described. 21,22 The products were obtained with yields ranging from 45 to 75%.…”

“…16 The CuAAC has been explored because of interesting characteristics such as mild reaction conditions, easy to execute, regioespecificity (only the 1,4-disubstituted isomer is obtained) and good yields. [17][18][19] In this paper we report the isolation of lupeol from Parahancornia fasciculata, synthesis of five 1,2,3-triazole derivatives of this triterpene by click chemistry, their evaluation for in vitro activity against chloroquine resistant P. falciparum W2 strain and cytotoxicity against Hep G2 cells.…”

Leishmanicidal, antiproteolytic, and mutagenic evaluation of alkyltriazoles and alkylphosphocholines

“…Though 56 M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT 3 In recent years, 'click chemistry' or the 'click reaction,' a reaction chemically referred 66 to as the copper-catalyzed azide-alkyne cycloaddition or CuAAC, for the efficient synthesis of 67 the 1,2,3-triazole nucleus, has attracted significant attention [9][10][11][12]. This heterocycle is easily 68 obtained by the CuAAC reaction [13] and has occupied an important position in medicinal 69 chemistry research [14]. The 1,2,3-triazole ring acts not only as a pharmacophore, but also as 70 a linker between two or more substances through a molecular hybridization strategy.…”

Modificação química de pululana e seu uso na produção de partículas para sistemas de liberação controlada de Indometacina

“…Outra desvantagem do uso de sais de Cu(I) é sua instabilidade termodinâmica, podendo ser oxidado para Cu(II) e/ou sofrer desproporcionamento para cobre metálico e Cu(II) no decorrer da reação. Desta forma, este procedimento requer atmosfera inerte e condições anidras.O mecanismo de reação de CuAAC, com as espécies de Cu(I) geradas in situ, a partir de um sal de Cu(II) encontra-se representado, de modo simplificado, na Figura 3.4(HIMO et al,2004;FREITAS et al, 2011). A primeira etapa do Em seguida, ocorre a contração desse intermediário por meio de uma associação transanular dos elétrons do nitrogênio vizinho ao metal com o orbital antiligante do carbono também ligado a um átomo de cobre, fornecendo a triazoila de cobre (7).…”