64267-19-2

Upstream product

• 110-89-4 piperidine 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 64-17-5 ethanol 
• 141-97-9 ethyl acetoacetate 
• 5977-14-0 acetoacetamido 
• 105-45-3 acetoacetic acid methyl ester 
• 75-93-4 methyl bisulfate 
• 10441-27-7 3-acetyl-7-hydroxy-chromen-2-one 
• 108-46-3 recorcinol 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 

Downstream Products

• 1350928-29-8 C₂₁H₂₀O₅S 
• 1350928-28-7 (E)-3-(3-(2-hydroxyphenyl)acryloyl)-7-methoxy-2H-chromen-2-one 
• 1616883-10-3 C₁₉H₁₅F₃N₂O₃ 
• 1616882-99-5 7-methoxy-3-methyl-1-(4-(trifluoromethyl)phenyl)chromeno[4,3-c]pyrazol-4(1H)-one 
• 1616883-11-4 C₁₈H₁₅ClN₂O₃ 
• 1616883-00-1 1-(4-chlorophenyl)-7-methoxy-3-methylchromeno[4,3-c]pyrazol-4(1H)-one 
• 1616883-12-5 C₁₈H₁₅BrN₂O₃ 
• 1616883-01-2 1-(4-bromophenyl)-7-methoxy-3-methylchromeno[4,3-c]pyrazol-4(1H)-one 
• 1616883-14-7 C₂₀H₂₀N₂O₃ 
• 1616883-03-4 1-(2,5-dimethylphenyl)-3-methylchromeno[4,3-c]pyrazol-4(1H)-one 
• 1616883-09-0 C₁₉H₁₅F₃N₂O₃ 
• 1616882-98-4 7-methoxy-3-methyl-1-(2-(trifluoromethyl)phenyl)chromeno[4,3-c]pyrazol-4(1H)-one 
• 1616883-13-6 C₁₈H₁₅FN₂O₃ 
• 1616883-02-3 1-(4-fluorophenyl)-7-methoxy-3-methylchromeno[4,3-c]pyrazol-4(1H)-one 

Relevant academic research and scientific papers

Vibrational spectra, structural conformations, scaled quantum chemical calculations and NBO analysis of 3-acetyl-7-methoxycoumarin

The powder form NIR-FT Raman and FT-IR spectra of 3-acetyl-7- methoxycoumarin (3A7MC) have been recorded in the regions 4000-400 and 3500-100 cm-1, respectively. The equilibrium geometry, vibrational frequencies, band intensities, NMR spectra, NBO analysis and UV-Vis spectral studies of the most stable conformer have been calculated by density functional B3LYP method with the 6-311G(d,p) basis set. A complete vibrational analysis has been attempted on the basis of experimental infrared and Raman spectra, the calculated wavenumber and intensity of the vibrational bands and the potential energy distribution over the internal coordinates. Information about the size, shape, charge density distribution and site of chemical reactivity of the molecules has been obtained by mapping the electron density isosurface with electrostatic potential surfaces (ESP). Natural bond orbital analysis has been carried out to understand the nature of different interactions responsible for the electron delocalization and the intramolecular charge transfer between the orbitals (n → π, n → σ, π → π).

An investigation on 3-acetyl-7-methoxy-coumarin Schiff bases and their Ru(ii) metallates with potent antiproliferative activity and enhanced LDH and NO release

New cyclometallated ruthenium(ii) complexes of 3-acetyl-7-methoxycoumarin-4N-substituted thiosemicarbazones were synthesized and characterized by analytical and spectral techniques. The crystal structures of the ligands H2L1-3 and complexes (1, 2 and 4) were confirmed by X-ray crystallography. The analysis showed that the ligands have undergone C-H activation at the C(4) carbon of the pyrone ring and acted in a tridentate fashion by binding through C, N and S atoms. CT-DNA and protein (BSA/HSA) binding studies were carried out to analyze their interaction with biomolecules. Good binding affinity with DNA was observed with intercalative binding mode, which was further confirmed by EB displacement and viscosity measurement studies. The quenching mechanism with BSA/HSA was found to be static. Three dimensional (3D) fluorescence measurements were carried out to validate the micro environmental changes in the serum albumins. Their antioxidant propensity and antimicrobial study insisted that the compounds displayed good spectrum of activity. Evaluation of their anticancer potential against MCF-7 (human breast cancer) and A549 (human lung carcinoma) cell lines revealed that the complexes exhibited better activity than the ligands and cisplatin. Further, the results of LDH and NO release assays supported the cytotoxic nature of the compounds. The non-toxic nature of the compounds was established by testing against the non-cancerous cell line HaCaT (human normal keratinocyte).

Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives

Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.

Coumarin-chalcone hybrids as inhibitors of MAO-B: Biological activity and in silico studies

Fourteen coumarin-derived compounds modified at the C3 carbon of coumarin with an α,β-unsaturated ketone were synthesized. These compounds may be designated as chalcocoumarins (3-cinnamoyl-2H-chromen-2-ones). Both chalcones and coumarins are recognized scaffolds in medicinal chemistry, showing diverse biological and pharmacological properties among which neuro-protective activities and multiple enzyme inhibition, including mitochondrial enzyme systems, stand out. The evaluation of monoamine oxidase B (MAO-B) inhibitors has aroused considerable interest as therapeutic agents for neurodegenerative diseases such as Parkinson’s. Of the fourteen chalcocumarins evaluated here against MAO-B, ChC4 showed the strongest activity in vitro, with IC50 = 0.76 ± 0.08 μM. Computational docking, molecular dynamics and MM/GBSA studies, confirm that ChC4 binds very stably to the active rMAO-B site, explaining the experimental inhibition data.

COUMARIN OXIME ESTER COMPOUNDS, PREPARATION AND USE THEREOF

The present invention relates to a coumarin (keto) oxime ester compound of formula (I), wherein n and R1, R2, R3, R4, R5, R6, and R7 are as defined in the specification. The compound has strong ultraviolet absorption in the range of 300 to 450 nm. After absorbing light energy, it can quickly transfer energy and continuously initiate polymerization. It has obvious advantages in terms of photosensitivity and pattern integrity, and is very suitable for radiation curing by UV-LED light source. In addition, the compound of formula (I) also has good thermal stability. The present invention also relates to a method for preparing the compound of formula (I) and use of the compound. The compound is suitable as a photoinitiator in a UV-LED light curing system and is suitable for the radiation wavelength of UV-LED light curing.

Ros inhibitory activity and cytotoxicity evaluation of benzoyl, acetyl, alkyl ester, and sulfonate ester substituted coumarin derivatives

Background: A number of non-steroidal anti-inflammatory drugs (NSAIDs) including aspirin, indomethacin, ibuprofen, flufenamic acid, and phenylbutazone are being clinically used to treat inflammatory disorders. These NSAIDs are associated with serious side

Synthesis and antiproliferative evaluation of novel biheterocycles based on coumarin and 2-aminoselenophene-3-carbonitrile unit

A series of novel coumarins with 2-amino-3-cyanoselenophen-5-yl unit on C-3 have been synthesized. These compounds prepared easily at room temperature, in a short time and in high yield. The importance of biheterocyclic units as dominant structural motif of coumarin derivatives has been well recognized. Anti-cancer activity screening on MCF-7 cell line allowed identification of 2-amino-5-(6-bromo-2-oxo-2H-chromen-3-yl)selenophene-3-carbonitrile with the highest level of cytotoxic activity with mean IC50 and cLogP (partition co-efficient) values 10.84 μM and 3.18, respectively. The most radical scavenging compound was also recognized. Graphic abstract: [Figure not available: see fulltext.].

Pyrazole–coumarin and pyrazole–quinoline chalcones as potential antitubercular agents

Pyrazole, coumarin, and quinoline are medicinally important moieties. In this study, two series of novel pyrazole–coumarin chalcones and pyrazole–quinoline chalcones were synthesized using multiple-step reactions. All the synthesized compounds were well c

Improved one-pot synthetic conditions for synthesis of functionalized fluorescent coumarin-thiophene hybrids: Syntheses, DFT studies, photophysical and thermal properties

We have synthesized coumarin-thiophene hybrids using stepwise and one-pot methods under MWI and CM conditions, and then report the findings and conclusions: one-pot is better than stepwise in terms of high yields and fastness of getting products, and MWI is better than CM in terms of purity of compounds, better yields, and reaction period. Even though both protocols were found to be efficient, the microwave-assisted irradiation reactions were identified to be better, environmentally friendly, cost-effective, mild, more efficient, less time consuming but with high purity. The two protocols were employed for the synthesis of the target coumarin-thiophene hybrids via the Gewald reaction in stepwise and in one-pot three-component. The dyes 3a-j were prepared in good to excellent yields. Although, we recorded better yields via the stepwise protocol (80–96%), for the synthesis of the target molecules, as compared to the one-pot (82–90%), the stepwise condition is fraught with many changes such as long reaction conditions, extra use of solvents for purification of intermediates, and long reaction durations. Photophysical activities of all the target derivatives were investigated using a combination of UV–vis and fluorescence spectroscopies in different solvents. The umbelliferon-like derivative 3g was further investigated for possible use as a pH sensor via deprotonation (using TBAOH) and reverse protonation (using TFA), and was found to be applicable as pH sensor both in organic medium (DMSO) and partial aqueous binary (DMSO/H2O, v/v, 9:1) medium. Again, the ground and the excited state properties of the umbelliferon-like derivative 3g and its deprotonated form were also studied using the quantum chemical calculations. Finally, the thermal properties of all the target compounds were investigated using TGA in order to test their potency and applicability as optical dyes. All the dyes 3a-j have high thermal stability therefore they can be applicable as optical dyes.

Discovery of coumarin Mannich base derivatives as multifunctional agents against monoamine oxidase B and neuroinflammation for the treatment of Parkinson's disease

Due to the complexity of the pathogenesis of Parkinson's disease (PD), multimodal treatment may achieve better results. In this study, a series of coumarin Mannich base derivatives were designed and synthesized as multifunctional agents for PD treatment. Among the derivatives, 3-(3-(dimethylamino)propanoyl)-7-hydroxy-5-methyl- 2H-chromen-2-one hydrochloride (24) exhibited the most potent and selective hMAO-B inhibitory activity, and anti-inflammatory and neuroprotective effects in the in vitro studies. It significantly attenuated PD-associated behavioural deficits in a 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced mouse model of PD. Furthermore, preliminary mechanistic studies indicated that 24 could selectively inhibit MAO-B activity, decrease the neuroinflammatory process, and protect tyrosine hydroxylase-immunopositive dopaminergic neurons. These results suggest that 24 is a promising multifunctional agent for effective therapy for PD.