Design and chemical synthesis of [1,2,4]triazol[1,5-c]pyrimidin-5-yl amines, a novel class of VEGFR-2 kinase inhibitors

Synthesis of Antimitotic Polyalkoxyphenyl Derivatives of Combretastatin Using Plant Allylpolyalkoxybenzenes

“…The respective five-membered aza-heterocyclic analogues of combretastatins were conveniently prepared from the respective carboxylic acid ( 12 ) or nitrile ( 24 ) precursors (Scheme ). Synthetic reactions leading to the 1,3,4-triazole ( 14 − 17 ) and 1,3,4-oxadiazole ( 18 − 23 ) derivatives involved preparation of the intermediate hydrazides ( 13 ). The respective 1,2,4-oxadiazole molecules 26 − 28 , 30 , and 31 were accessed from 24 via this modified procedure .…”

Crystal structure of ethyl 2-(5-methyl-4H-1,2,4-triazol-3-yl)acetate, C7H11N3O2

“…There has been much research interest in triazole due to its biological activities [1,2]. In this work, we report the crystal structure of the title compound, 2-(5-methyl-4H-1,2,4-triazol-3-yl)acetate ( Fig.…”

Synthesis and Fluorescence of (E)‐3‐Aryl‐2‐(5‐aryl‐4H‐1,2,4‐triazol‐3‐yl) Acrylonitriles

“…Unfortunately, none of compounds Ia , IIb , and III (Figure 1) showed interesting biological activities in the in vitro cytotoxic tests on an array of human cancer cell lines [9] . In 2009, Kiselyov and collaborators reported the design and chemical synthesis of [1,2,4]triazol[1,5‐ c ]pyrimidin‐5‐yl amines, a novel class of VEGFR‐2 kinase inhibitors, ( E )‐2‐(5‐methyl‐4 H ‐1,2,4‐triazol‐3‐yl)‐3‐(pyridin‐4‐yl)acrylonitrile ( IIc ) (Figure 1) being one of the key intermediate for their synthesis [11] . They easily prepared it by Knoevenagel condensation of 2‐(5‐methyl‐4 H ‐1,2,4‐triazol‐3‐yl)acetonitrile with 4‐pyridylaldehyde, and obtained it as a major trans ‐isomer, in 71–75 % yield.…”

“…[9] In 2009, Kiselyov and collaborators reported the design and chemical synthesis of [1,2,4]triazol [1,5-c]pyrimidin-5-yl amines, a novel class of VEGFR-2 kinase inhibitors, (E)-2-(5-methyl-4H-1,2,4triazol-3-yl)-3-(pyridin-4-yl)acrylonitrile (IIc) (Figure 1) being one of the key intermediate for their synthesis. [11] They easily prepared it by Knoevenagel condensation of 2-(5-methyl-4H-1,2,4-triazol-3-yl)acetonitrile with 4-pyridylaldehyde, and obtained it as a major trans-isomer, in 71-75 % yield. Finally, it is interesting to note that compounds of type III (Figure 1) have been prepared by reaction of 5-benzyl-1H-1,2,4-triazol-3-ylacetonitrile with aromatic aldehydes, and tested for their hypotensive effect in rats.…”