Synthesis of 3-(2-nitrovinyl)-4H-chromones: useful scaffolds for the construction of biologically relevant 3-(pyrazol-5-yl)chromones
authors Soengas, RG; Silva, VLM; Ide, D; Kato, A; Cardoso, SM; Paz, FAA; Silva, AMS
nationality International
journal TETRAHEDRON
author keywords Pyrazoles; Chromones; Henry reaction; Antioxidant; Glucosidase inhibitor
keywords ALPHA-GLUCOSIDASE INHIBITORS; ANTIOXIDANT ACTIVITY; PYRAZOLE DERIVATIVES; MEDIATED REACTION; AGENTS; NITROOLEFINS; IDENTIFICATION; ANTIBACTERIAL; HYDRAZONES; SCAVENGERS
abstract The Henry-type Barbier addition of bromonitromethane to 3-formylchromone, immediately followed by acetylation and concomitant elimination to afford nitroalkenes in excellent yield and total (E)-selectivity is described. Cycloaddition of N-methylhydrazones with the obtained nitroalkenes gave the corresponding pyrazoles. Among the prepared pyrazoles, derivative 6j, which contains a catechol moiety, showed simultaneously a potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity and an alpha-glucosidase inhibitory activities. (C) 2016 Elsevier Ltd. All rights reserved.
publisher PERGAMON-ELSEVIER SCIENCE LTD
issn 0040-4020
year published 2016
volume 72
issue 23
beginning page 3198
ending page 3203
digital object identifier (doi) 10.1016/j.tet.2016.04.042
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000376799800008
  ciceco authors
  impact metrics
journal analysis (jcr 2017):
journal impact factor 2.377
5 year journal impact factor 2.255
category normalized journal impact factor percentile 60.526
dimensions (citation analysis):
altmetrics (social interaction):



 


Apoio

1suponsers_list_ciceco.jpg