5725-79-1Relevant articles and documents
Targeting adenosine receptors with coumarins: Synthesis and binding activities of amide and carbamate derivatives
Matos, Maria Jo?o,Gaspar, Alexandra,Kachler, Sonja,Klotz, Karl-Norbert,Borges, Fernanda,Santana, Lourdes,Uriarte, Eugenio
, p. 30 - 34 (2013)
Objectives With the aim of finding the structural features governing binding activity and selectivity against adenosine receptors (ARs), several 3-subtituted coumarins with amide (compounds 3-6) and carbamate (7-9) functions were synthesized. To study its possible influence on the binding activity and selectivity, a hydroxyl substituent was also introduced at position 4 of the coumarin moiety. Methods A new series of coumarins (3-9) were synthesized and evaluated by radioligand binding studies towards ARs. Key findings None of the 4-hydroxy derivatives (4, 8 and 9) showed binding affinity for any of the ARs. None of the compounds interacted with the hA2B AR (Ki > 100 000 nm). Compounds 3, 5, 6 and 7 had different activity profiles with dissimilar binding affinity and selectivity towards human A1, A 2A and A3 ARs. Conclusions The most remarkable derivative is compound 7, which presents the best affinity and selectivity for the A 3 adenosine receptor (Ki = 5500 nm).
A convergent paired electrochemical synthesis of new heterocyclic compounds. Reaction of benzoquinones with 3-Amino-4-hydroxycoumarin
Nematollahi,Karbasi
, p. 48 - 58 (2011)
Electrochemical oxidation of catechols (1) has been studied in the presence of cathodically generated 3-amino-4- hydroxycoumarin (3a) as a nucleophile in aqueous solutions, using cyclic voltammetry and controlled-potential coulometry. The results indicate that the o-benzoquinones derived from catechols (1) participate in Michael addition reaction with 3-amino-4- hydroxycoumarin (3a) to form the corresponding new heterocyclic compounds (7) (oxidized form of coumestan derivatives). The electrochemical process consists of a multi-step including (a) cathodic reduction of 4-hydroxy-3-nitrocoumarin (3) to 3-amino-4- hydroxycoumarin (3a), (b) anodic oxidation of catechols (1) to related o-benzoquinone (2), (c) the Michael addition reaction of 3- amino-4-hydroxycoumarin (3a) to o-benzoquinone (2), and (d) anodic oxidation of formed adduct. The paired electrochemical synthesis of compounds 7a and 7b has been successfully performed in a one-pot process at carbon rods as working and counter electrodes in an undivided cell.
Highly selective light-up Al3+ sensing by a coumarin based Schiff base probe: Subsequent phosphate sensing DNA binding and live cell imaging
Sheet, Sanjoy Kumar,Sen, Bhaskar,Thounaojam, Romita,Aguan, Kripamoy,Khatua, Snehadrinarayan
, p. 101 - 111 (2016/08/30)
A coumarin based simple fluorescent “turn-on” probe, 4-Hydroxy-3-[(2-hydroxy-5-methoxybenzylidene)-amino]-chromen-2-one (HMC), to detect metal ion based on the chelation enhanced fluorescence (CHEF), was synthesized by condensing 3-amino-4-hydroxycoumarin and 2-hydroxy-5-methoxybenzaldehyde. It was found to be highly selective and sensitive sensor for Al3+ in 90% aqueous methanol (MeOH: 0.01?M HEPES Buffer; 9:1; v/v) at pH 7.4 in fluorescence spectroscopy. Fluorescence intensity enhancement along with 10?nm blue shift was observed only in the presence of Al3+. The HMC binds Al3+ in 1:1 stoichiometry with a binding constant, Ka?=?(9.9?±?0.04)?×?103?M?1 and the detection limit was calculated to be as low as 1.62?μM. The binding mode of interaction with Al3+ and the chelate complex formation was supported with the help of a 1H NMR spectroscopy titration, ESI–MS and also by theoretical studies. Moreover, the HMC·Al3+ ensemble subsequently detected the biologically important phosphate ions and nucleotides via fluorescence quenching. The live cell imaging study indicated that HMC is highly efficient in the detection of exogenous Al3+ in living cell.
New Coumarin Derivatives as Anti-Breast and Anti-Cervical Cancer Agents Targeting VEGFR-2 and p38α MAPK
Batran, Rasha Z.,Dawood, Dina H.,El-Seginy, Samia A.,Ali, Mamdouh M.,Maher, Timothy J.,Gugnani, Kuljeet S.,Rondon-Ortiz, Alejandro N.
, (2017/09/05)
Breast and cervical cancers are the most common gender-specific cancers affecting women worldwide. In this investigation, we highlighted the synthesis, VEGFR-2 and p38α MAPK inhibitory activity of new series of fluorinated coumarin-based derivatives featuring a variety of bioactive chemical moieties attached or fused to the coumarin nucleus at the 3 and/or 4 position. The bioactive inhibitors were further assessed for their anti-proliferative effect against human MCF-7 breast cancer and HeLa cervical cancer cell lines, respectively. Most of the tested compounds showed potent preferential inhibition effects against human VEGFR-2 and remarkable anticancer activities in the human breast cancer cell line MCF-7. Compounds 29, 24, and 2 displayed the highest inhibitory activity against VEGFR-2 (94% inhibition) and they were the most potent anticancer agents toward MCF-7 cancer cells with IC50 values of 7.90, 8.28, and 8.30 μg/mL, respectively. Compound 13 inhibited p38α MAPK phosphorylation with a significant reduction in % cell viability against HeLa cancer cells at 10 and 30 μM. Docking experiments carried out on VEGFR-2 and p38 MAPK crystallographic structures revealed that the active compounds bind to the active sites through H-bonds, arene–cation, and hydrophobic π–π interactions. QSAR analysis demonstrated considerable correlation coefficient (R2 = 0.76969) and root mean square error (RMSE = 0.10446) values. Also, the residual values between the experimental pIC50 and predicted pIC50 are very close, indicating the reliability of the established QSAR model.
