945915-48-0Relevant academic research and scientific papers
Synthesis of 3-amlno-8-azachromans and 3-amino-7-azabenzofurans via inverse electron demand dlels-alder reaction
Badarau, Eduard,Suzenet, Franck,Finaru, Adriana-Lusninita,Guillaumet, Gerald
experimental part, p. 3619 - 3627 (2009/12/01)
The synthesis of 3-amino-8-azachromans and 3-amino-7-azabenzofurans derivatives is reported. The synthetic strategy is based on an inverse electron demand Diels-Alder approach, which employs 1,2,4-triazines that are judiciously substituted with amino alkynols. This approach permits the variation of the substituent on the aromatic core and on the amine moiety, as well as of the size of the nonaromatic ring.
Synthesis and pharmacological evaluation of phenylethynyl[1,2,4] methyltriazines as analogues of 3-methyl-6-(phenylethynyl)pyridine
Carroll, F. Ivy,Kotturi, Sharadsrikar V.,Navarro, Hernán A.,Mascarella, S. Wayne,Gilmour, Brian P.,Smith, Forrest L.,Gabra, Bichoy H.,Dewey, William L.
, p. 3388 - 3391 (2008/02/11)
Procedures were developed for the synthesis of 3-methyl-5-phenylethynyl[1, 2,4]triazine (4), 6-methyl-3-phenylethynyl[1,2,4]triazine (5), and 5-methyl-3-phenylethynyl[1,2,4]triazine (6a) as analogues of 2-methyl-6-(phenylethynyl)pyridine (2). The compounds were evaluated for antagonism of glutamate-mediated mobilization of internal calcium in an mGluR5 in vitro efficacy assay. The most potent of the three analogues was 6a. Twenty additional analogues of 6a were synthesized and evaluated for mGluR5 antagonist efficacy. The most potent compounds were 3-(3-methylphenylethynyl)-5-methyl[1,2, 4]triazine (6b), 5-(3-chlorophenylethynyl)-5-methyl[1,2,4]triazine (6c), and 3-(3-bromophenylethynyl)-5-methyl[1,2,4]triazine (6d).
