Discovery and optimization of oxadiazole-based FLAP inhibitors

Síntese, caracterização e atividade antitumoral in vitro de uma série de 1,2,4-oxadiazois 3,5-substituídos

“…Nos últimos 40 anos, o 1,2,4-oxadiazol heterociclo tem sido amplamente explorado trazendo um grande número de compostos exibindo diversas atividades biológicas. A literatura relata um conjunto diversificado de aplicações (Figura 2) para o núcleo de 1,2,4-oxadiazol na química medicinal [5,6], como antiasmático (1) [7], antidiabético (2) [8], antitumoral (3, 4 e 5) [9,10,11], anti-inflamatório (6) [12], antioxidante (7) [13] antimicrobiano (8 e 9) [14], anti-Alzheimer (10) [15,16]. Além disso, derivados de 1,2,4-oxadiazol também encontraram aplicação como cristais líquidos (11) supramoleculares e HEDMs [17,18,19].…”

“…Figura 2: Exemplos de 1,2,4-Oxadiazóis com aplicações na química medicinal, química de materiais e na química agrícola [7][8][9][10][11][12][13][20][21][22].…”

Synthesis and Antibacterial Evaluation of 3,5-Diaryl-1,2,4-oxadiazole Derivatives

“…Then, 33 mmol of a nitrile derivative (1-4) and 20 mL of ethanol were added to the reaction medium, which was kept under stirring and refluxed for 5 h. After this period, the product, an amidoxime (5-8), was recrystallized from water (Scheme 1). 19 Synthesis of acyl chloride (9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) Thionyl chloride (5 mL) was slowly added to a roundbottomed flask containing carboxylic acid (3.1 mmol). The medium was refluxed for 2 h. Only acyl chloride (9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) remained in the flask after the excess thionyl chloride was removed by distillation.…”

“…19 Synthesis of acyl chloride (9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) Thionyl chloride (5 mL) was slowly added to a roundbottomed flask containing carboxylic acid (3.1 mmol). The medium was refluxed for 2 h. Only acyl chloride (9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19) remained in the flask after the excess thionyl chloride was removed by distillation. 20 Synthesis of the 1,2,4-oxadiazol derivatives (20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39) The newly synthesized acyl chloride dissolved in toluene (10 mL) was slowly added to a solution of amidoxime (2.5 mmol) dissolved in toluene (40 mL) in a 250 mL round-bottomed flask at 25 o C and under constant stirring.…”

“…4 Although the 1,2,4-oxadiazole heterocycle was first synthesized in 1884, 5 it was only in the 1990s that this nucleus aroused interest within the scientific community. 6 The literature reports a diverse set of applications for the 1,2,4-oxadiazole core in medicinal chemistry, 7,8 such as antiasthmatic, 9 antidiabetic, 10 antitumoral, 11 anti-inflammatory, 12 antioxidant, 12 and antimicrobial. 13 Different parameters are used to quantify these biological activities, such as half maximal inhibitory concentration (IC 50 ), half maximal effective concentration (EC 50 ) or minimum inhibition concentration (MIC) (Figure 2).…”