127073-91-0

Basic information

• Product Name: 3-(3′,4′-dimethoxyphenyl)-6-methylcoumarin
• Synonyms: 3-(3′,4′-dimethoxyphenyl)-6-methylcoumarin
• CAS NO: 127073-91-0
• Molecular Weight: 296.323
• Mol File: 127073-91-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 3-(3′,4′-dimethoxyphenyl)-6-methylcoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3′,4′-dimethoxyphenyl)-6-methylcoumarin(127073-91-0)
• EPA Substance Registry System: 3-(3′,4′-dimethoxyphenyl)-6-methylcoumarin(127073-91-0)

Safety Data

• Hazardous Substances Data: 127073-91-0(Hazardous Substances Data)

Upstream product

• 106-44-5 p-cresol 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 60075-23-2 3,4-dimethoxyphenylacetic acid hydrazide 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 55720-88-2 homoveratric anhydride 

Downstream Products

• 949580-77-2 6-bromomethyl-3-(3,4-dimethoxyphenyl)chromen-2-one 
• 1387531-39-6 trans-3-(3,4-dimethoxyphenyl)-6-styrylcoumarin 
• 1442435-70-2 3-(3′,4′-dihydroxyphenyl)-6-methylcoumarin 

Relevant articles and documents

3-Arylcoumarins as highly potent and selective monoamine oxidase B inhibitors: Which chemical features matter?

Monoamine oxidase B inhibitory activity is closely regulated by the interaction of the small molecules with the enzyme. It is therefore desirable to use theoretical approaches to design rational methods to develop new molecules to modulate specific interactions with the protein. Here, we report such methods, and we illustrate their successful implementation by studying six synthetized 3-arylcoumarins (71–76) based on them. Monoamine oxidase B inhibition is essential to maintain the balance of dopamine, and one of its major functions is to combat dopamine degradation, a phenomenon linked to Parkinson's disease. In this work, we study small-molecule inhibitors based on the 3-arylcoumarin scaffold and their monoamine oxidase B selective inhibition. We show that 3D-QSAR models, in particular CoMFA and CoMSIA, and molecular docking approaches, enhance the probability to find new interesting inhibitors, avoiding very costly and time-consuming synthesis and biological evaluations.

Remarkable antioxidant properties of a series of hydroxy-3-arylcoumarins

In the present work we synthesized a series of hydroxy-3-arylcoumarins (compounds 1-9), some of them previously described as MAO-B selective inhibitors, with the aim of evaluating their antioxidant properties. Theoretical evaluation of ADME properties of all the derivatives was also carried out. From the ORAC-FL, ESR and CV data it was concluded that these derivatives are very good antioxidants, with a very interesting hydroxyl, DPPH and superoxide radicals scavenging profiles. In particular compound 9 is the most active and effective antioxidant of the series (ORAC-FL = 13.5, capacity of scavenging hydroxyl radicals = 100%, capacity of scavenging DPPH radicals = 65.9% and capacity of scavenging superoxide radicals = 71.5%). Kinetics profile for protection fluorescein probe against peroxyl radicals by addition of antioxidant molecule 9 was also performed. Therefore, it can operate as a potential candidate for preventing or minimizing the free radicals overproduction in oxidative-stress related diseases.

Extensive SAR and computational studies of 3-{4-[(benzylmethylamino)methyl] phenyl}-6,7-dimethoxy-2H-2-chromenone (AP2238) derivatives

AP2238 was the first compound published to bind both anionic sites of the human acetylcholinesterase, allowing the simultaneous inhibition of the catalytic and the amyloid-β pro-aggregating activities of AChE. Here we attempted to derive a comprehensive structure-activity relationship picture for this molecule, affording 28 derivatives for which AChE and BChE inhibitory activities were evaluated. Selected compounds were also tested for their ability to prevent the AChE-induced Aβ-aggregation. Moreover, docking simulations and molecular orbital calculations were performed.