24350-99-0

Upstream product

• 60034-94-8 2-methoxy-5-methyl-N-methylbenzamide 
• 75-56-9 methyloxirane 
• 259872-72-5 3-ethyl-7-methoxy-4-methyl-3H-isobenzofuran-1-one 

Downstream Products

• 7734-92-1 (S)-8-hydroxy-3,5-dimethylisochroman-1-one 
• 24349-82-4 3,4-dihydro-(3R)-5-dimethyl-8-hydroxyisocoumarin 

Relevant academic research and scientific papers

Dihydroisocoumarin derivative and preparation method and application thereof

The present invention discloses a dihydroisocoumarin derivative and preparation method and application thereof, the dihydroisocoumarin derivative having a structure as shown in formula (I) or (II). The method of preparing dihydroisocoumarin derivatives of

Discovery, synthesis, biological evaluation and molecular docking study of (R)-5-methylmellein and its analogs as selective monoamine oxidase A inhibitors

(R)-5-Methylmellein (5-MM), the major ingredient in the fermented mycelia of the medicinal fungus Xylaria nigripes (called Wuling Shen in Chinese)? was found to be a selective inhibitor against monoamine oxidase A (MAO-A) and might play an important role in the clinical usage of this edible fungus as an anti-depressive traditional Chinese medicine (TCM). Based on the discovery and hypothesis, a variety of (R)-5-MM analogs were synthesized and evaluated in vitro against two monoamine oxidase isoforms (MAO-A and MAO-B). Most synthetic analogs showed selective inhibition of MAO-A with IC50 values ranging from 0.06 to 29 μM, and compound 13aR is the most potent analog with high selectivity (IC50, MAO-A: 0.06 μM; MAO-B: >50 μM). Interestingly, the enzyme kinetics study of 13aR indicated that this ligand seemed to bind in the MAO-A active site according to so-called “tight-binding inhibition” mode. The molecular docking study of 13aR was thereafter performed in order to rationalize the obtained biological results.

Synthesis of 3-ethylphthalides and their conversion to 3-methyl-3,4- dihydro-isocoumarins: Synthesis of (±)-5-methylmellein

Ortho-directed lithiation of N-methylbenzamides 1a-f with n-BuLi in ether/THF followed by alkylation with propanal gives 3-ethylphthalides 2a-f which on treatment with conc. H2SO4 or AlCl3 afford 3-methyl-3,4- dihydroisocoumarins 3a-f.

Isocoumarins : Part III - Synthesis of Methyl- and Methylenedioxydihydroisocoumarins and a New Synthesis of (+/-)-5-Methylmellein

o-Lithio-N-methylbenzamide upon condensation with propylene oxide gives 3-methyldihydroisocoumarin.Similarly o-lithio-N-methyl-p-toluamide upon condensation with ethylene oxide and propylene oxide give 6-methyl- and 3,6-dimethyldihydroisocoumarin.A similar condensation of o-lithio-N-methyl-m-toluamide with ethylene oxide gives 5-methyldihydroisocoumarin but condensation with propylene oxide gives 3,5-dimethyl- and 3,7-dimethyldihydroisocoumarins.The method has been used to synthesize (+/-)-5-methylmellein.The synthesis of 5,6-methylenedioxydihydroisocoumarin from o-lithio-N-methylpiperonylamide is also described. 3-Methyl-6,7-methylenedioxydihydroisocoumarin has been synthesized by an acid-catalyzed cyclization reaction.