1338596-79-4

Upstream product

• 553-86-6 benzofuran-2(3H)-one 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 1190439-39-4 3-(2'-methoxy)phenyl-6-methylcoumarin 

Relevant academic research and scientific papers

Organocatalytic condensation-ring opening-annulation cascade reactions between N-Bocindolin-2-ones/benzofuran-2(3 H)-ones and salicylaldehydes for synthesis of 3-arylcoumarins

An organocatalytic cascade synthesis of 3-arylcoumarins has been developed. Mediated by 1,8-diazabicyclo[5,4,0]-undec-7-ene or tetramethylguanidine, a number of 3-arylcoumarins were obtained in good to excellent yields via condensation-ring opening-annulation between N-Bocindolin-2-ones/benzofuran-2(3H)-ones and salicylaldehydes. This method was featured by a broad scope of reactants, mild conditions, and simple operation.

Method for organically catalyzing and efficiently synthesizing 3-aromatic coumarin compound

The invention discloses a method for organically catalyzing and efficiently synthesizing a 3-aromatic coumarin compound. DBU and/or TMG are/is adopted as a catalyst(s), and a compound in a formula A and a compound in a formula B are reacted to obtain a compound in a formula C as shown in the below figure, wherein X is NBoc, NAc or O; R1 is selected from hydrogen, alkyl, alkoxy, halogen and nitryl; R3 is selected from hydrogen, alkyl, alkoxy, halogen and nitryl. The method has the characteristics of wide reaction substrate, moderate condition, simplicity in experiment operation, and convenience in aftertreatment.

Copper-mediated synthesis of coumestans via C(sp2)-H functionalization: Protective group free route to coumestrol and 4′-O-methylcoumestrol

A simple and efficient two step synthesis of coumestans is described. The key reaction in the synthesis is the use of easily available Cu(OAc)2 for C[sbnd]H functionalization of 3-(2-hydroxyphenyl)coumarin to give coumestan ring system via formal oxidative cyclization. This approach provided a short protective group free route to naturally occurring coumestrol and 4′-O-methylcoumestrol.

Synthesis and evaluation of 6-methylcoumarin derivatives as potent and selective monoamine oxidase B inhibitors

A new series of 6-methyl-3-phenylcoumarins (3a-c and 5a-o) and 6-methyl-3-heteroarylcoumarins (5p-s) have been designed, synthesized and evaluated as monoamine oxidase inhibitors. The results demonstrated that a large proportion of the synthesized compounds selectively inhibited monoamine oxidase B with IC50 values in the sub-micromolar range. Among them, compound 5n (IC50 = 0.0601 μM) exhibited the most potent inhibitory activity and the highest selectivity for monoamine oxidase B (SI > 1664-fold). In addition, the possible binding model of the active compound 5n was measured by docking it into the active site of the hMAO-B complex structure. The results showed that compound 5n interacted with the well-known binding pocket of MAO-B, and a π-π interaction was found between the phenyl ring at position 3 of the coumarin and the phenyl ring of Tyr 326. Consequently, we supplied useful information about the interaction between the enzyme and inhibitor, and developed the 6-methyl-3-phenylcoumarin scaffold as an agent for multifaceted brain disorders. This journal is

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.

Synthesis and study of a series of 3-arylcoumarins as potent and selective monoamine oxidase B inhibitors

New series of 6-substituted-3-arylcoumarins displaying several alkyl, hydroxyl, halogen, and alkoxy groups in the two benzene rings have been designed, synthesized, and evaluated in vitro as human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitors.