21829-30-1Relevant academic research and scientific papers
Facile and green synthesis of 1,4-dihydropyridine derivatives in n-butyl pyridinium tetrafluoroborate
Wu, Xiao Yun
, p. 454 - 459 (2012)
l,4-Dihydropyridine derivatives were synthesized from the one-pot condensation of aldehydes, acetoacetates, and ammonium acetate in room-temperature ionic liquid n-butyl pyridinium tetrafluoroborate ([BPy][BF4]). Compared with classical Hantzsch reaction conditions, this new method has the advantage of excellent yields, short reaction time, and easy workup. The recovered ionic liquid could be recycled for at least five runs without losing its activity. Taylor & Francis Group, LLC.
1,4-Dihydropyridine antagonist activities at the calcium channel: A quantitative structure-activity relationship approach
Coburn,Wierzba,Suto,Solo,Triggle,Triggle
, p. 2103 - 2107 (2007/10/02)
The effect of 46 1,4-dihydropyridine-type calcium channel antagonists on the tonic contractile response of longitudinal muscle strips of guinea pig ileum was determined. 2,6-Dimethyl-3,5-dicarbomethoxy-4-phenyl-1,4-dihydropyridine (13) and 13 ortho-, 15 meta-, and seven para-monosubstituted and 10 polysubstituted aromatic derivatives of 13 were studied. The pharmacological activities of the monosubstituted derivatives were best correlated by eq 10, log 1/C = 0.68π + 2.50σ(m) - 0.47L(meta) - 3.40B1(para) + 11.31, which had a correlation coefficient of 0.89. The full data set was best correlated by eq 11, log 1/C = 0.62π + 1.96σ(m) - 0.44L(meta) - 3.26B1(para) - 1.51L(meta) + 14.23, which had a correlation coefficient of 0.90. Equations of similar form but involving an ortho steric term were found to correlate the radioligand binding data for this class of compounds.
Studies directed toward ascertaining the active conformation of 1,4-dihydropyridine calcium entry blockers
Rovnyak,Andersen,Gougoutas,Hedberg,Kimball,Malley,Moreland,Porubcan,Pudzianowski
, p. 936 - 944 (2007/10/02)
A series of unsymmetrically substituted 4-phenyl-1,4-dihydropyridine calcium entry blockers were investigated for their ability to relax potassium-contracted rabbit aortic smooth muscle and to competitively displace [3H][nitrendipine from its specific binding sites on guinea pig myocardial membranes in order to delineate the pharmacologically active conformer with respect to the position of the aromatic substituents (synperiplanar or antiperiplanar). The data show that the 1,4-dihydropyridine receptor distinguishes between 2',3'-disubstituted phenyldihydropyridines and 2',5'-disubstituted analogues as measured by changes of vasodilation and receptor affinity in vitro. The IC50 values for vasorelaxation by the analogues presented here correlate best with the K(d) values for binding to the predominant receptor of two coexisting dihydropyridine binding sites in the guinea pig myocardium. We report the first observation of an antiperiplaner orientation of an o-phenyl substituent in the X-ray structure of 2-chlorophenyl analogue 3. Using nuclear Overhauser enhancement, we have developed a method that also demonstrates that an ortho (chloro or nitro) substituent on the phenyl ring does not preclude the presence of either synperiplanar or antiperiplanar phenyl rotamer in solution. These experimental findings contrast with the accepted belief that o-phenyl substituents essentially force these 1,4-dihydropyridines into the synperiplanar conformation exclusively.
