14415-44-2Relevant academic research and scientific papers
Crystal structure and interaction of 6-amino coumarin with nitrite ion for its selective fluorescence detection
Guha, Subarna,Lohar, Sisir,Bolte, Michael,Safin, Damir A.,Das, Debasis
, p. 225 - 235 (2012)
6-Amino coumarin has been established as an efficient nitrite ion selective fluorescent sensor. The developed method shows linearity up to 1.6 × 10-6 molL-1 of nitrite ion concentration. Interference from other common anions is almost negligible. The reagent shows strong binding affinity towards nitrite ion as evident from its binding constant value (5.8 × 104), estimated by Stern-Volmer method. Some real samples were analyzed. Single crystal X-ray structure of the reagent is reported. Preliminary computational studies on the molecular level interaction between the reagent and nitrite ion were performed by density functional theory (DFT, B3LYP) method. Copyright
New copper(I) complex with a coumarin as ligand with antibacterial activity against flavobacterium psychrophilum
Aldabaldetrecu, Maialen,Parra, Mick,Soto, Sarita,Arce, Pablo,Tello, Mario,Guerrero, Juan,Modak, Brenda
, (2020)
A new copper (I) complex, [Cu(NN1)2](ClO4), was synthesized, where NN1 was a imine ligand 6-((quinolin-2-ylmethylene)amino)-2H-chromen-2-one obtained by a derivatization of natural compound coumarin. The structural characterization in solution was done by NMR techniques, UV-Vis and cyclic voltammetry. The potential antibacterial effect of [Cu(NN1)2](ClO4), was assessed for F. psychrophilum isolated 10094. F. psychrophilum is a Gram-negative bacterium which causes diseases such as bacterial cold-water disease and rainbow trout fry syndrome, causing large economic losses in the freshwater salmonid aquaculture industry. This complex show to have antibacterial activity against F. psychrophilum 10094 at non-cytotoxic concentration in cell line derived from trout (F. psychrophilum 10094 IC50 16.0 ± 0.9; RT-GUT IC50 53.0 ± 3.1 μg/mL).
Synthesis and biological evaluation of (2,5-dihydro-1H-pyrrol-1-yl)-2H- chromen-2-ones as free radical scavengers
Balabani, Anna,Hadjipavlou-Litina, Dimitra J.,Litinas, Konstantinos E.,Mainou, Maria,Tsironi, Crystal-Catherine,Vronteli, Anastasia
, p. 5894 - 5901 (2011)
The allylation of aminocoumarins in the presence of excess of anhydrous K2CO3 and allyl bromide to diallylaminocoumarins is described. The Ring Closing Metathesis reaction of the later with the Grubbs' 1rst generation catalyst under reflux or MW irradiation has resulted mainly to (2,5-dihydro-1H-pyrrol-1-yl)coumarins and (1H-pyrrol-1-yl)coumarins. The new compounds were tested in vitro for their ability: (i) to interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH) stable free radical, (ii) to inhibit lipid peroxidation, (iii) to scavenge the superoxide anion, (iv) to inhibit the activity of soybean lipoxygenase LO and (v) to scavenge hydroxyl radicals. Most of them were found to be potent lipid peroxidation inhibitors in vitro. The majority of the compounds showed significant hydroxyl radical scavenging activity. Compounds 11a and 12c presenting higher LO inhibitory activity as well as compound 17 were found to present a promising antioxidant and LO inhibitory profile.
Synthesis, NMR, X-ray and UV/Vis characterization and preliminary luminescence study of some boron β-iminoenolates having 6-aminocoumarin moiety
Dou?ová, Hana,?im?nek, Petr,Almonasy, Numan,R??i?ková, Zdeňka
, p. 60 - 71 (2016)
Five coumarin-based polarized ethylenes (enaminoketones, enaminoester and enaminoamide) were prepared using the condensation of the parent β-dicarbonyl compounds with 6-aminocoumarin. Reaction of the polarized ethylenes with an appropriate source of trivalent boron gave corresponding boron β-iminoenolates having either BF2 or BPh2 fragment. The prepared iminoenolates were characterized by means of multinuclear magnetic resonance in solution, single-crystal X-ray diffraction and UV/Vis spectroscopy. A preliminary luminescence study of the iminoenolates as well as their parent enamines was done. The compounds exhibited fluorescence in a solid state as well as in a frozen 2-methyltetrahydrofuran at 77 K. Exploratory tests showed promising AIE/AIEE properties of the tested compounds. On the other hand, no fluorescence in a solution state (with one exception) was observed.
New series of 6-substituted coumarin derivatives as effective factor Xa inhibitors: Synthesis, in vivo antithrombotic evaluation and molecular docking
Amin, Kamelia M.,Abdel Gawad, Nagwa M.,Abdel Rahman, Doaa E.,El Ashry, Mohamed K.M.
, p. 31 - 43 (2014)
Despite recent progress in antithrombotic therapy, there's still an unmet medical need for safe and orally available anticoagulants. Encouraged by the marked antithrombotic and anticoagulant activities of some coumarin derivatives, twenty-three new N-coumarinyl-4-amidinobenzamides 4a-f and 6-heterocycle substituted coumarin derivatives 5, 6a,b, 10a-e, 12a-e and 14a-d were synthesized and evaluated for their in vivo antithrombotic activity. The most active congeners were the unsubstituted amidine 4a (36.5 s), coumarinyl oxadiazole 5 (42.3 s), bis coumarinyl oxadiazole 6b (37.8 s) and coumarinyl pyrazole 10b (38.5 s) that presented prothrombin time (PT) values comparable to the reference drug warfarin (42.3 s). Furthermore, docking studies were undertaken to gain insight into the possible binding mode of these compounds with the coagulation factor Xa (FXa) binding site.
Intramolecular charge transfer in coumarin based donor-acceptor systems: Formation of a new product through planar intermediate
Phukan, Smritakshi,Saha, Mithu,Pal, Amarta Kumar,Bhasikuttan,Mitra, Sivaprasad
, p. 67 - 79 (2015)
Fluorescence behavior and intramolecular charge transfer (ICT) property of N,N′-dimethylamino substituted anil derivative of coumarinyl amine was studied by steady state and time-resolved fluorescence spectroscopy in combination with density functional theory calculation. Quantitative analysis of the effect of solvent hydrogen bonding on several spectral parameters was done using multiple regression analysis based on Kamlet-Taft model. The present system shows an additional long wavelength fluorescence band almost instantaneously in presence of methanol in sharp contrast to the model unsubstituted analogue. This new fluorescence band is believed to be due to the formation of a new isomer (cis-type) through a planar intermediate. While there is a substantial barrier (～50 kJ mol-1) in the ground state, the isomerization process in the excited state in polar-protic environment proceeds very fast and believed to be catalyzed by hydrogen bond formation at the imine nitrogen atom in combination with stabilization of the resulting species through ICT.
Structure, photophysics, electrochemistry, DFT calculation, and in-vitro antioxidant activity of coumarin Schiff base complexes of Group 6 metal carbonyls
Datta, Papia,Mukhopadhyay, Ambika Prasad,Manna, Prasenjit,Tiekink, Edward R.T.,Sil, Parames Chandra,Sinha, Chittaranjan
, p. 577 - 588 (2011)
N-[(2-Pyridyl)methyliden]-6-coumarin (L) is synthesized by the condensation of 6-aminocoumarin and pyridine-2-carboxaldehyde. Group-6 tetracarbonyl complexes, [M(CO)4(L)] (M = Cr, Mo, and W) are synthesized and characterized by mass spectrometry and NMR, FT-IR and UV-visible spectroscopy. X-ray crystal structure of [Cr(CO)4(L)] shows N(pyridine), N(imine) chelation to chromium(0). A supramolecular chain is formed by C-H?O and π?π interactions. The ligand and the complexes are fluorescent. Cyclic voltammetry of the complexes exhibit quasireversible M(I)/M(0) redox couple. The complexes exhibit potential antioxidant property both in cell free and in-vitro studies and highest activity is observed to [W(CO)4(L)]. Density functional theory (DFT) computation has been performed to correlate with the electronic configuration, composition of wave functions with the UV-visible spectra and redox properties.
Synthesis and in vitro cytotoxicity of aminocoumarin platinum(II) complexes
Kokotos, George,Theodorou, Vassiliki,Tzougraki, Chryssa,Deforce, Dieter L.D.,Van Den Eeckhout, Elfreide G.
, p. 2165 - 2168 (1997)
A number of cis-dichloro[bis(aminocoumarin)platinum(II) complexes have been synthesized and evaluated for their in vitro cytotoxicity against Caco-2T cells. The complex with 7-amino-4-trifluoromethylcoumarin as ligand has been found to be the most active (IC50 10 μ/ml) in this study.
Design, synthesis and agricultural evaluation of derivatives of N-Acyl-N-(m-fluoro-benzyl)-6-amino-coumarin
Jin, Yan,Ding, Yin-hao,Dong, Jing-jing,Wei, Yan,Hao, Shuang-hong,Feng, Bai-cheng
, p. 798 - 804 (2020/08/19)
ABTRACT: This study aims to design and synthesize a series of N-Acyl-N-(m-fluoro- benzyl)-6- amino-coumarins through the principle of active substructure stitching, which are based on the core structure of N-(m-fluoro-benzyl)-6-amino-coumarin. The structures of target compounds e1–e25 have been characterized by 1H NMR, 13C NMR, ESI-MS and elemental analysis. Meanwhile, their agricultural activity have been evaluated in two weeds (Amaranth and Crabgrass) and four widespread noxious pathogens (V.mali, B.cinerea, F.axysporium and C.bacteria). The herbicidal activity results showed that almost all synthetic molecules have a greater impact on the stem system than on the root. Excellent inhibition rates were discovered from compounds e2–e5 and e20–e23 against Amaranth on stems, which were above 58percent(20 mg/L), 68percent(100 mg/L) respectively. Compounds e2 and e21 also exhibited striking inhibition on stems growth of both weeds. Anti-pathogenic activity showed that all the compounds exerted a better inhibitory activity on B.cinerea at 20 ppm compared to control carbendazim. All the heterocyclic substituted compounds (e17–e24, >57percent) made a better influence than the control (54.1percent) at the100 ppm. This research provides promising herbicidal and anti-pathogenic agents that have the better effects and can be potential for further development.
Design, synthesis, and antifungal evaluation of novel coumarin-pyrrole hybrids
Zhang, Shuguang,Tan, Xin,Liang, Chaogen,Zhang, Weihua
, p. 450 - 458 (2020/11/30)
A series of coumarin derivatives bearing a pyrrole scaffold were designed, prepared, and assessed for their in vitro antifungal activities against six phytopathogenic fungi. The antifungal activity screening results suggest that some synthesized hybrids exhibited potential fungicidal activities against the tested fungi. In particular, compounds 6j, 6k, 6o, 6p, and 6r displayed significant antifungal effects against Rhizoctorzia solani, and possessed EC50 values of 3.94, 7.75, 6.38, 6.25, and 7.67 μg/ mL, respectively. The above activities are more potent than the commercialized fungicide Boscalid (11.52 μg/mL) and Osthole (9.79 μg/mL). These results provide a significant reference for further rational design of coumarin-based fungicides.
