17754-91-5

Usage

InChI:InChI=1/C20H20N4O/c1-3-24(4-2)14-10-9-13-11-15(19(21)25-18(13)12-14)20-22-16-7-5-6-8-17(16)23-20/h5-12,21H,3-4H2,1-2H3,(H,22,23)

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 91-68-9 3-diethylaminophenol 
• 4414-88-4 1H-benzimidazol-2-acetonitrile 
• 17754-90-4 4-(Diethylamino)salicylaldehyde 

Downstream Products

• 27425-55-4 coumarin 7 
• 1227043-14-2 methyl 4-{[3-diethylamino]-7H-chromeno[2',3':4,5]pyrimido[1, 6-a]benzimidazol-7-ylideneamino}benzoate 
• 1227043-08-4 N,N-diethyl-7-[(4-nitrophenyl)imino]-7H-chromeno[2',3':4,5]pyrimido[1,6-a]benzimidazol-3-amine 
• 1227043-16-4 N,N-diethyl-7-[(4-bromophenyl)imino]-7H-chromeno[2',3':4,5]pyrimido[1,6-a]benzimidazol-3-amine 
• 1227043-12-0 N,N-diethyl-7-[(4-trifluoromethyl)imino]-7H-chromeno[2',3':4,5]pyrimido[1,6-a]benzimidazol-3-amine 
• 1227043-10-8 4-{[3-diethylamino]-7H-chromeno[2',3':4,5]pyrimido[1,6-a]benzimidazol-7-ylideneamino}benzonitrile 
• 1433952-59-0 C₂₆H₂₂BF₂IN₄O 
• 1433952-58-9 C₂₇H₂₅BF₂N₄O₂ 
• 1433952-57-8 C₂₇H₂₅BF₂N₄O 
• 1433952-60-3 C₃₁H₃₁BF₂N₄OSi 
• 1433952-56-7 C₂₆H₂₃IN₄O 
• 51347-33-2 C₂₇H₂₆N₄O₂ 
• 51347-31-0 C₂₇H₂₆N₄O 
• 52372-39-1 3-diethylamino-7-imino-7H-chromeno[3',2'-3,4]pyrido[1,2-a]benzimidazole-6-carbonitrile 

Relevant academic research and scientific papers

Synthesis of fluorescent cationic coumarin dyes with rigid molecular structures to improve lightfastness and their related modacrylic dyed fibers

In this study, three novel cationic, fluorescent, coumarin dyes (6a, 6b and 6c) with rigid molecular structures were synthesized and characterized by spectroscopic studies. The photochemical behavior (UV light) of these dyes was studied in ethanol and DMF

Benzazole substituted iminocoumarins as potential antioxidants with antiproliferative activity

Background: Benzazole and coumarin derivatives are one of the most privileged het-erocyclic substructures in the medicinal chemistry with well-known biological features, which include a wide range of versatile biological activities as well as excellent spectroscopic characteris-tics thus offering their potential application in many research fields. Objective: The prepared iminocoumarins were synthesized to evaluate their antioxidative potential by using ABTS and FRAP assays and in vitro antiproliferative activity. Methods: A series of coumarin derivatives containing a 2-benzazole motif were synthesized and evaluated for their antioxidative capacity and antiproliferative activity. Their molecular structure incorporates a push-pull functionality: an electron donor donating group at the 7-position with an electron-withdrawing group, such as benzimidazole, benzothiazole and imidazopyridine fragment at the 3-position. Results: The iminocoumarins bearing different substituents on 7-position were evaluated for their antiproliferative activity on tree cancer cells with only 4 compounds showing the antiproliferative activity. The most active derivative was N,N-diethylamino substituted benzimidazole derivative 4d and imidazo[4,5-b]pyridine analogue 6b, both also displayed selective activity toward CEM with submicromolar inhibitory concentration (0.059 μM; 0.17 ± 0.09, respectively). The inhibitory effect of 4d and 6b derivatives on the cell-cycle progression of HeLa cells was studied. A flow cy-tometric analysis of the HeLa cells indicated an appreciable cell-cycle arrest in a dose-dependent manner. Antioxidant properties were studied by ABTS and FRAP assays and obtained results revealed that the most promising antioxidant has proven to be compound 3b while other compounds, in general, showed moderate to very low antioxidative capacity in both assays. Conclusion: Unsubstituted benzimidazole derivatives bearing hydroxyl group on iminocoumarin nuclei exhibited the most prominent antioxidant potential in ABTS assay (3b; 40.5 ± 0.01). The most significant and selective antiproliferative activity was displayed by compounds 4d and 6b (0.059 μM; 0.17 ± 0.09, respectively), which were chosen as lead compounds for further optimization and rational design to obtain more active and selective antiproliferative agents.

Novel compound having excellent durability against sunlight and fluorescent dye composition containing the same

The present invention relates to a novel compound having excellent light durability and a fluorescent dye composition including the same. It is applicable to fluorescent products exhibiting high fluorescence characteristics and high visibility. Furthermor

Construction of red-emitting iminocoumarin-based fluorescent borate complexes with a large Stokes shift

Tetra-hydro-quinoxaline (THQ) moiety was used as the electron donor in the construction of a series of red-emitting iminocoumarin-based borate dyes with good fluorescent quantum yields, large Stokes shifts and long-wavelength emissions. These dyes could s

Plastic colorant fluorescent red GK and preparation method thereof

The invention belongs to the technical field of plastic colorants, and particularly relates to a plastic colorant fluorescent red GK and a preparation method thereof. The plastic colorant fluorescentred GK comprises the following raw materials in parts by weight: 37-39 parts of ethylene glycol monoethyl ether, 0.9 - 1.1 parts of malononitrile and 4.9- 5.1 parts of 3 -(1H-benzimidazole -2-yl)-N, N-diethyl -2-imine -2H-1-benzopyran- 7-amine. The preparation method of the plastic colorant fluorescent red GK comprises the following steps: 1) condensation: sequentially adding ethylene glycol monoethyl ether, malononitrile and 3- (1H-benzimidazole- 2-yl)-N, N-diethyl -2-imine -2H-1-benzopyran -7-amine in proportion into a condensation kettle, heating to 125-135 DEG C, reacting for 5.5-6.5 hours, cooling to 45-55 DEG C, discharging, and filtering to obtain a filter cake; and 2) filtering and drying: drying the filter cake in an environment with normal pressure and a temperature of 60-80 DEGC to prepare the plastic colorant fluorescent red GK. The preparation method of the plastic colorant fluorescent red has the characteristics of short reaction time, mild reaction conditions, low equipment requirements and high reaction yield.

Novel Iminocoumarin Derivatives: Synthesis, Spectroscopic and Computational Studies

Three novel iminocoumarin derivatives with high quantum yield are synthesized from 3-benzimidazole substituted coumarin and different aromatic aldehydes. The photophysical behavior of the synthesized compounds was studied using UV-visible and fluorescence spectroscopy in polar and non-polar solvents. The compounds show absorption maxima at around 450 nm and emission maxima at around 500 nm. The quantum yields of compounds in dichloromethane and chloroform are more than 0.90. The absorption, emission and quantum yield of compounds are dependent on the polarity of solvents. Along with an intense absorption, these compounds show shoulder absorption peak in the studied solvents. The solvent polarity plots revealed the charge transfer process in the synthesized molecules from donor to acceptor. Density Functional Theory and Time Dependent Density Functional Theory computations have been used to have more understanding of the structural, molecular, electronic and photophysical parameters of the dyes. The dyes were characterized by FT-IR, 1H NMR, 13C NMR and mass spectral analysis.

Fluorescent boron(iii) iminocoumarins (Boricos)

Complexation of iminocoumarin derivatives with BF3· OEt2 provides novel NN boron(iii) dyes exhibiting high absorption coefficients and quantum yields as great as 81%. The excellent chemical stability of these dyes enables the graftin

A novel colorimetric and fluorescent pH sensor derived from iminocoumarin and thiophene-carboxaldehyde

A novel colorimetric and fluorescent pH sensor derived from iminocoumarin and thiophene-carboxaldehyde was designed and synthesized. The structures of the dye and related compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectra. Color change from green to yellow of the new sensor solution in ethanol-water with the decrease in the pH value from 7 to 2 was observed by the naked eye. Under acidic conditions, the intensity of the maximum fluorescence emission peak of the sensor increased gradually with the decrease in the acidity of the solution (the increase in the pH value from 2 to 7) and attained to the maximum value at about pH 6. Under basic conditions, the fluorescence intensity of the emission peak of the sensor did not exhibit a distinct change at pH ≤ 11.85, and the fluorescence was quenched at pH 13.36, concomitant with the green color of the solution turning pale. The sensor can be used as a fluorescent pH probe in the presence of common metal cations and anions without interference.

Articles Comprising Benzopyran Colorants, Method Of Manufacture, And Method Of Use

An article comprising the compound of Formula (I) wherein X is hydrogen or a radical of Formula (II), R1 independently at each occurrence is a C1-C20 aliphatic radical, a C3-C10 cycloaliphatic radical, or a C3-C10 aromatic radical; R2, R3, R4 and R5 are independently at each occurrence a halogen, a nitro group, a cyano group, a hydroxy group, a C1-C20 aliphatic radical, a C3-C20 cycloaliphatic radical, or a C6-C20 aromatic radical; and “n”, “q”, and “p” are each independently integers having a value of 0 to 3, and “m” is an integer having a value of 0 to 4.