1338596-78-3

Upstream product

• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 621-37-4 m-hydroxyphenylacetic acid 
• 1798-09-0 m-methoxyphenylacetic acid 
• 1190439-37-2 3-(3-methoxyphenyl)-6-methyl-2H-chromen-2-one 

Downstream Products

• 1338596-80-7 6-methyl-3-[3-(2-oxopropoxy)phenyl]coumarin 

Relevant academic research and scientific papers

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

Synthesis and evaluation of 6-substituted 3-arylcoumarin derivatives as multifunctional acetylcholinesterase/monoamine oxidase B dual inhibitors for the treatment of Alzheimer's disease

Considering the complex etiology of Alzheimer's disease (AD), multifunctional agents may exhibit important properties against this disease. A series of 6-substituted 3-arylcoumarins (5a-t) were designed, synthesized and evaluated as cholinesterase (ChE) and monoamino oxidase (MAO) inhibitors. Among them, compounds 5o [IC50, 195 nM for human acetylcholinesterase (hAChE), selectivity index, SI (human butyrylcholinesterase, hBuChE/hAChE) = 145; IC50, 63.5 nM for human monoamine oxidase-B (hMAO-B), SI (human monoamine oxidase-A, hMAO-A/hMAO-B) = 25] and 5p [IC50, 185 nM for hAChE, SI (hBuChE/hAChE) = 182; IC50, 196 nM for hMAO-B, SI (hMAO-A/hMAO-B) > 510] were found to selectively inhibit both hAChE and hMAO-B with IC50 values in the nanomolar range. The abilities of 5o and 5p to bind to hAChE and hMAO-B were confirmed by molecular docking and kinetic studies. Moreover, 5o and 5p were found to exhibit significant inhibition of self-induced Aβ42 aggregation (61% and 52%, at 20 μM), have antioxidant properties (0.81 and 1.17 trolox equivalent by ABTS assay), provide neuroprotection against Aβ42-induced cytotoxicity and blood-brain barrier (BBB) penetration capacity (PAMPA-BBB+), and are thus potential anti-Alzheimer agents with balanced activities. Overall, the study provided meaningful information for further development of multifunctional drugs for AD therapy.

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.