68306-20-7Relevant academic research and scientific papers
One-pot synthesis and radical scavenging activity of novel polyhydroxylated 3-arylcoumarins
Svinyarov, Ivan,Bogdanov, Milen G.
, p. 198 - 206 (2014)
An unexpected domino rearrangement brought about the development of a novel one-pot procedure for synthesis of coumarins. This protocol allowed the gram-scale synthesis of a variety of polyhydroxylated derivatives 3a-p, from readily available starting materials at a low cost. Based on two proven intermediates, a probable mechanism consisting of boron tribromide induced demethylation/lactone ring opening/elimination/isomerization/lactone ring closure reaction sequence of in situ formed 3-aryl-3,4-dihydroisocoumarin-4- carboxylic acids was deduced. Compared to the common methods, used for the synthesis of coumarins, the proposed herein possesses great advantages, such as mild conditions, good yields for short reaction time, simple work-up procedure and easy isolation of the final products. The structure of the newly synthesized compounds 3a-p was established by spectroscopic methods (1H NMR, 13C NMR, IR, MS and HRMS) and their radical scavenging activity was evaluated in vitro against 1,1-diphenyl-2-picrylhydrazyl free radical (DPPH). The results obtained show that compounds 3g-p posses higher radical scavenging activity (3.16 SC;bsubesub[μM] ; 6.82) than well-known antioxidants such as trolox, protocatechuic acid, caffeic acid and gallic acid (SC50 [μM] = 9.34, 8.83, 9.48, 5.33, respectively), which is a precondition for promising antioxidant activity of these compounds to be expected.
Synthesis and antioxidant activity of polyhydroxylated trans-restricted 2-arylcinnamic acids
Miliovsky, Mitko,Svinyarov, Ivan,Prokopova, Elena,Batovska, Daniela,Stoyanov, Simeon,Bogdanov, Milen G.
, p. 2555 - 2575 (2015/03/04)
A series of sixteen polyhydroxylated trans-restricted 2-arylcinnamic acid analogues 3a-p were synthesized through a one-pot reaction between homophthalic anhydrides and various aromatic aldehydes, followed by treatment with BBr3. The structure of the newly synthesized compounds was confirmed by spectroscopic methods and the configuration around the double bond was unequivocally estimated by means of gated decoupling 13C-NMR spectra. It was shown that the trans-cinnamic acid fragment incorporated into the target compounds' structure ensures the cis-configuration of the stilbene backbone and prevents further isomerization along the carbon-carbon double bond. The antioxidant activity of compounds 3a-p was measured against 1,1-diphenyl-2-picrylhydrazyl (DPPH?), hydroxyl (OH?) and superoxide (O2?-) radicals. The results obtained showed that the tested compounds possess higher activities than natural antioxidants such as protocatechuic acid, caffeic acid and gallic acid. Moreover, it was shown that a combination of two different and independently acting fragments of well-known pharmacological profiles into one covalently bonded hybrid molecule evoke a synergistic effect resulting in higher than expected activity. To rationalize the apparent antioxidant activity and to establish the mechanism of action, a SAR analysis and DFT quantum chemical computations were also performed.
