Synthesis of E- and Z-pyrazolylacrylonitriles and their evaluation as novel antioxidants.
A facile synthesis of (Z)- and (E)-2-(5-arylpyrazol-3-yl)-3-(pyrrol-2-yl)acrylonitriles and (Z)-2-(1,3-diarylpyrazol-5-yl)-3-pyrrol-2-yl)acrylonitriles, and isomerisation of (Z)-2-(5-arylpyrazolyl)acrylonitriles to (E)-2-(5-arylpyrazolyl)acrylonitriles under basic conditions have been reported. (Z)-2-(1,3-Diarylpyrazolyl)acrylonitriles did not undergo isomerisation under the similar conditions. New compounds were identified on the basis of their spectral data (1H-, 13C-, 1H-1H COSY, NOESY, NOE, HMQC NMR, IR, UV and EI mass). The structures of one acrylonitrile and five of their precursor 6-arylpyran-2-ones and cyanomnethylpyrazoles were confirmed by X-ray crystallographic studies. Effects of pyrazolylacrylonitriles and their precursors on rat liver-microsomal lipid peroxidation were evaluated in vitro with a view to establish structure activity relationship and to identify a lead compound.
Parmar
V S
VS
Department of Chemistry, University of Delhi, India. vparmar.duchem@axcess.net.in
Kumar
A
A
Prasad
A K
AK
Singh
S K
SK
Kumar
N
N
Mukherjee
S
S
Raj
H G
HG
Goel
S
S
Errington
W
W
Puar
M S
MS
D000181:Acrylonitrile / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology*; D002855:Chromatography, Thin Layer / Q000379:methods; D018360:Crystallography, X-Ray; D004353:Drug Evaluation, Preclinical; D020128:Inhibitory Concentration 50; D007536:Isomerism; D015227:Lipid Peroxidation / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008862:Microsomes, Liver / Q000187:drug effects / Q000378:metabolism; D015394:Molecular Structure; D009249:NADP / Q000378:metabolism; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
C121643:2-(3-(3-methoxyphenyl)pyrazol-5-yl)-3-(2-pyrrolyl)acrylonitrile; C121644:2-(3-(4-methoxyphenyl)pyrazol-5-yl)-3-(2-pyrrolyl)acrylonitrile; D000975:Antioxidants; D011720:Pyrazoles; D009249:NADP; D000181:Acrylonitrile