32986-89-3Relevant academic research and scientific papers
Effect of substituents on the 13C NMR chemical shifts of para-substituted α-phenyl-β-pyridylacrylic acids
Jovanovi?,Mi?i?-Vukovi?,Drmani?,?anadi
, p. 39 - 41 (2007/10/03)
The 13C NMR spectra of para-substituted α-phenylcinnamic and 3- and 4-pyridylacrylic acids, with a wide range of substituents effects, were determined in deuterated dimethylsulfoxide (DMSO-d6). The effect of substituents in both the α-phenyl and β-pyridine groups in these acids is investigated using linear free energy relationships and multiple regression analysis as applied to 13C NMR chemical shifts of the C(α) and C(β) of the ethylenic bond and the carboxylic group carbon. Dissection of the α-phenyl substituent effects into the inductive and resonance components, using the dual substituent parameter (DSP) method, points to a blend of inductive and resonance effects in the π-electronic system.
Acrylamide derivatives as antiallergic agents. 2. Synthesis and structure-activity relationships of N-[4-[4-(diphenylmethyl)-1-piperazinyl]butyl]-3-(3-pyridyl)acrylamides
Nishikawa,Shindo,Ishii,Nakamura,Kon,Uno
, p. 583 - 593 (2007/10/02)
A new series of 3-(3-pyridyl)acrylamides 16, 17, 19, and 26, and 5-(3-pyridyl)-2,4-pentadienamides 20-25 were prepared and evaluated for their antiallergic activity. Several of these compounds exhibited more potent inhibitory activities than the parent compounds 1a [(E)-N-[4 [4-(diphenylmethyl)-1-piperazinyl]butyl]-3-(3-pyridyl)acrylamide] against the rat passive cutaneous anaphylaxis (PCA) reaction and the enzyme 5-lipoxygenase. Particularly, 4-[4-(diphenylmethyl)-1-piperazinyl]butyl]-3-(6-methyl-3-pyridyl)acrylamide (17p) showed an ED50 value of 3.3 mg/kg po in the rat PCA test, which was one-fifth of ketotifen and oxatomide. As compared with ketotifen and oxatomide, compound 17p (AL-3264) possessed a better balance of antiallergic properties due to inhibition of chemical mediator release, inhibition of 5-lipoxygenase, and antagonism of histamine.
Structural Effects of the Acidity of E-α-Phenyl-β-arylacrilic Acids
Maccarone, Emanuele,Mamo, Antonino,Perrini, Giancarlo,Torre, Michele
, p. 395 - 398 (2007/10/02)
The dissociation equilibrium constants of some E-α-phenyl-β-arylacrilic acids (Ar=2-pyridyl, 3-pyridyl, 4-pyridyl, 1-naphthyl, 2-naphthyl, anthracen-9-yl) have been measured in 80percent aqeous 2-methoxyethanol at 25 deg C., The pKa values of these acids, together with those of p-substituted phenyl, 2-furyl, 2-thienyl and selenophen-2-yl derivitives, have been rationalized by an equation involving separate contributions of polar, conjugative and steric effects of heterocycles.The pKa values of some E-α-phenyl-β-alkylacrilic acids (alk=methyl; ethyl; n-propyl; i-propyl; n-butyl; i-butyl) are also reported.
