Synthesis of 3-(2-nitrovinyl)-4H-chromones: Useful scaffolds for the construction of biologically relevant 3-(pyrazol-5-yl)chromones

Raquel G. Soengas; Vera L.M. Silva; Daisuke Ide; Atsushi Kato; Susana M. Cardoso; Filipe A. Almeida Paz; Artur M.S. Silva

doi:10.1016/j.tet.2016.04.042

Synthesis of 3-(2-nitrovinyl)-4H-chromones: Useful scaffolds for the construction of biologically relevant 3-(pyrazol-5-yl)chromones

Raquel G. Soengas^*, Vera L.M. Silva, Daisuke Ide, Atsushi Kato, Susana M. Cardoso, Filipe A. Almeida Paz, Artur M.S. Silva

^*Corresponding author for this work

Hospital Pharmacy

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

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 α-glucosidase inhibitory activities.

Original language	English
Pages (from-to)	3198-3203
Number of pages	6
Journal	Tetrahedron
Volume	72
Issue number	23
DOIs	https://doi.org/10.1016/j.tet.2016.04.042
State	Published - 2016/06/09

Keywords

Antioxidant
Chromones
Glucosidase inhibitor
Henry reaction
Pyrazoles

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2016.04.042

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title = "Synthesis of 3-(2-nitrovinyl)-4H-chromones: Useful scaffolds for the construction of biologically relevant 3-(pyrazol-5-yl)chromones",

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 α-glucosidase inhibitory activities.",

keywords = "Antioxidant, Chromones, Glucosidase inhibitor, Henry reaction, Pyrazoles",

author = "Soengas, {Raquel G.} and Silva, {Vera L.M.} and Daisuke Ide and Atsushi Kato and Cardoso, {Susana M.} and {Almeida Paz}, {Filipe A.} and Silva, {Artur M.S.}",

note = "Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd.",

year = "2016",

month = jun,

day = "9",

doi = "10.1016/j.tet.2016.04.042",

language = "英語",

volume = "72",

pages = "3198--3203",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "23",

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TY - JOUR

T1 - Synthesis of 3-(2-nitrovinyl)-4H-chromones

T2 - Useful scaffolds for the construction of biologically relevant 3-(pyrazol-5-yl)chromones

AU - Soengas, Raquel G.

AU - Silva, Vera L.M.

AU - Ide, Daisuke

AU - Kato, Atsushi

AU - Cardoso, Susana M.

AU - Almeida Paz, Filipe A.

AU - Silva, Artur M.S.

PY - 2016/6/9

Y1 - 2016/6/9

N2 - 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 α-glucosidase inhibitory activities.

AB - 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 α-glucosidase inhibitory activities.

KW - Antioxidant

KW - Chromones

KW - Glucosidase inhibitor

KW - Henry reaction

KW - Pyrazoles

UR - http://www.scopus.com/inward/record.url?scp=84964800744&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2016.04.042

DO - 10.1016/j.tet.2016.04.042

M3 - 学術論文

AN - SCOPUS:84964800744

SN - 0040-4020

VL - 72

SP - 3198

EP - 3203

JO - Tetrahedron

JF - Tetrahedron

IS - 23

ER -

Synthesis of 3-(2-nitrovinyl)-4H-chromones: Useful scaffolds for the construction of biologically relevant 3-(pyrazol-5-yl)chromones

Abstract

Keywords

ASJC Scopus subject areas

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