Journal
TETRAHEDRON LETTERS
Volume 50, Issue 27, Pages 3809-3812Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.04.062
Keywords
Knoevenagel condensation; VEGFR-2; 7,8-Dihydro[1,2,4]triazol[1,5-c]pyrimidin-5-yl amines; Cyclization; Angiogenesis; Kinase inhibitor
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The Letter describes a facile approach to 7,8-dihydro[1,2,4]triazol[1,5-c]pyrimidin-5-yl amines, a novel class of potent inhibitors of vascular endothelial growth factor receptor II (VEGFR-2). The synthetic sequence is centered around preparation of the key 3(5)-cyanomethyl-1,2,4-triazole intermediates and their Knoevenagel condensation with aromatic aldehydes. A subsequent three-step conversion of Knoevenagel adducts involving a reduction of vinyl nitriles followed by the reaction of the resulting amines with aryl isothiocyanates and cyclization of the respective thioureas yielded targeted heterocycles as a 1:1 mixture of tautomers. A representative molecule featured sound activity against VEGFR-2 in both enzymatic and cellular assays. (C) 2009 Elsevier Ltd. All rights reserved.
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