22367-92-6

Upstream product

• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 90-02-8 salicylaldehyde 
• 1268149-45-6 C₁₃H₁₄N₂O₃ 
• 89-95-2 2-methyl-benzyl alcohol 
• 2444-36-2 2'-chloro-benzeneacetic acid 
• 55720-88-2 homoveratric anhydride 
• 83814-21-5 N-<3,4-dimethoxyphenyl(thioacetyl)>morpholine 

Downstream Products

• 51924-87-9 2-(3,4-dimethoxyphenyl)benzofuran 

Relevant academic research and scientific papers

Ultrasound-Assisted Solvent-Free Parallel Synthesis of 3-Arylcoumarins Using N-Acylbenzotriazoles

An ultrasound-assisted one-pot acylation/cyclization reaction between N-acylbenzotriazoles and 2-hydroxybenzaldehydes has been developed for the synthesis of substituted 3-arylcoumarins. Using ultrasound not only allows rapid and clean conversion but also simplifies experimental setup and parallel workup leading to rapid generation of 3-arylcoumarin libraries under mild, solvent-free, and chromatography-free conditions.

Synthesis and Evaluation of Coumarin-Resveratrol Hybrids as 15-Lipoxygenaze Inhibitors

A series of coumarin-resveratrol hybrids, 3-arylcoumarin derivatives 3a-u, were synthesized through the intermolecular condensation reaction of various salicylaldehydes and phenylacetic acids in the presence of 1,4-diazabicyclo[2.2.2]octane under solvent-free conditions. All the synthesized compounds were screened for their inhibitory potency against soybean 15-lipoxygenase. Among them, three compounds (3c, 3j, and 3q) showed good enzyme-inhibitory activities. GRAPHICAL ABSTRACT.

3-Arylcoumarins: Synthesis and potent anti-inflammatory activity

Chronic inflammation is the persistent and excessive immune response and can lead to a variety of diseases. Aiming to discover new compounds with anti-inflammatory activity, we report herein the synthesis and biological evaluation of 3-arylcoumarins. Thirty five 3-arylcoumarins were prepared through Perkin condensation and further acid-promoted hydrolysis if necessary. In lipopolysaccharide-activated mouse macrophage RAW264.7 cells, 6,8-dichloro-3-(2-methoxyphenyl)coumarin (16) and 6-bromo-8-methoxy-3-(3-methoxyphenyl)coumarin (25) exhibited nitric oxide production inhibitory activity with the IC50 values of 8.5 μM and 6.9 μM, respectively, providing a pharmacological potential as anti-inflammatory agents.

3-phenylcoumarins as inhibitors of HIV-1 replication

We have synthesized fourteen 3-phenylcoumarin derivatives and evaluated their anti-HIV activity. Antiviral activity was assessed on MT-2 cells infected with viral clones carrying the luciferase gene as reporter. Inhibition of HIV transcription and Tat function were tested on cells stably transfected with the HIV-LTR and Tat protein. Six compounds displayed NF-κB inhibition, four resulted Tat antagonists and three of them showed both activities. Three compounds inhibited HIV replication with IC50 values 25 μM. The antiviral effect of the 4-hydroxycoumarin derivative 19 correlates with its specific inhibition of Tat functions, while compound 8, 3-(2-chlorophenyl) coumarin, seems to act through a mechanism unrelated to the molecular targets considered in this research.

Synthesis of 2-phenylbenzofuran derivatives and selective binding activities on estrogen receptor

An improved chemical reaction protocol with short time and easy work-up was described here for 2-phenylbenzofuran derivatives. The final purified products, 2-phenylbenzofuran derivatives 5a-g and the intermediate diols 4a-g, were evaluated for their estrogen receptor (ER) binding affinity and selective activity in vitro. Among these fourteen tested compounds, 4g and 5g showed higher binding affinity on ER subtypes, ERα and ERβ. Compound 4g exhibited preferable ERα binding, while 5g was more estrogen selective for ERβ. The molecular docking was also performed to explore the detailed interactive interface between ER and the compounds.

A novel synthesis of 3-aryl coumarins and evaluation of their antioxidant and lipoxygenase inhibitory activity

A series of coumarin analogues bearing a substituted phenyl ring on position 3 were synthesized via a novel methodology, through an intermolecular condensation reaction of 2-hydroxyacetophenones and 2-hydroxybenzaldehyde, with imidazolyl phenylacetic acid active intermediates. The in vitro antioxidant activity of the synthesized compounds was evaluated using two different antioxidant assays (radical scavenging ability of DPPH stable free radical and inhibition of lipid peroxidation induced by the thermal free radical AAPH). Moreover, the ability of the compounds to inhibit soybean lipoxygenase was determined as an indication of potential anti-inflammatory activity.

Efficient synthesis of 3-substituted coumarins

The Mukaiyama's esterification protocol, using 2-chloro-1-methylpyridinium iodide-triethylamine reagent, has been successfully exploited to provide rapid access to a variety of 3-substituted coumarins in satisfactory yields.

A convenient one-pot synthesis of 4-methyl-3-phenyl-, 3-aryl- and 3-aryl-4-phenylcoumarins

Thermal condensation of 2′-hydroxyacetophenones 1a-e with phenylacetic acid 2a in refluxing diphenyl ether gives 4-methyl-3-phenylcoumarins 3a-e. Similarly, reaction of 2-hydroxybenzaldehydes 1f-m and 2-hydroxybenzo-phenones 1n-p with phenylacetic acids 2a-d gives the corresponding 3-arylcoumarins 3f-m and 3-aryl-4-phenylcoumarins 3n-p respectively. Formation of esters 4 and 5 and benzofuran 6 is also observed.

A novel one-step synthesis of 3-phenyl-, 4-methyl-3-phenyl- And3-phenyl-4-styrylcoumarins using DCC-DMSO

2-Hydroxybenzaldehydes 1 react with phenylacetic acid and its methoxy derivatives 2 in the presence of DCC in DMSO to afford 3-phenylcoumarins 3. Under identical conditions, 2-hydroxy-acetophenones 4 and 2'-hydroxychalcones 7 give rise to the corresponding 4-methyl-3-phenyl- and 3-phenyl-4-styrylcoumarins 6 and 8, respectively.