- Dihydroisocoumarin derivative and preparation method and application thereof
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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
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- Dihydroisocoumarin derivative and preparation method and application thereof
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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
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- Isocoumarin derivative as well as preparation method and medical application thereof
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The invention belongs to the technical field of chemical medicines, and relates to an isocoumarin compound of general formula (I) and a preparation method and medical application, of the isocoumarin compound in preparation of medicines for treating and mo
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- Discovery, synthesis, biological evaluation and molecular docking study of (R)-5-methylmellein and its analogs as selective monoamine oxidase A inhibitors
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(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.
- Huang, Chao,Xiong, Juan,Guan, Hui-Da,Wang, Chang-Hong,Lei, Xinsheng,Hu, Jin-Feng
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p. 2027 - 2040
(2019/04/10)
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- Toward the total synthesis of citreamicin η: Synthesis of the pentacyclic core and GAB-ring annelation model studies
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A short 11-step synthesis of the pentacyclic core of the polycyclic xanthone antibiotic citreamicin η has been completed. Although the basic approach was inspired by our previous explorations of polycyclic xanthone chemistry, the present report features some new insights into the Moore rearrangement and offers some improvements to our original methodology that include additions of aryllithiums to squarate esters, additions of cerium acetylides to hindered ketones utilizing PDA as an internal indicator, and the use of cyclic di-tert-butylsilyl (DTBS) ethers to protect electron-rich benzyl alcohols toward ionization under acidic conditions. We also developed an improved protocol for selective o-bromination of phenols utilizing N-bromosuccinimide (NBS) and tetramethylguanidine (TMG) that promises to be generally useful. Finally, we developed a modular approach for the synthesis of isoquinolones and dihydro-5H-oxazolo[3,2-b]isoquinoline-2,5(3H)-diones that features a novel sequence of alkoxycarbonylation, acetone arylation, transamidation.
- Blumberg, Shawn,Martin, Stephen F.
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p. 4981 - 4993
(2018/05/23)
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- Ruthenium-NHC-Diamine Catalyzed Enantioselective Hydrogenation of Isocoumarins
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A novel and practical chiral ruthenium-NHC-diamine system is disclosed for the enantioselective hydrogenation of isocoumarins, which provides a new concept to apply (chiral) NHC ligands in asymmetric catalysis. A variety of optically active 3-substituted 3,4-dihydroisocoumarins were obtained in excellent enantioselectivities (up to 99% ee). Moreover, this methodology was utilized in the synthesis of O-methylmellein, mellein, and ochratoxin A.
- Li, Wei,Wiesenfeldt, Mario P.,Glorius, Frank
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supporting information
p. 2585 - 2588
(2017/03/08)
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- Reactions of 3-(1-Hydroxyalkyl)phthalides with Acids: Synthesis of (Z)-3-Alkylidenephthalides and 3-Alkyl-8-hydroxyisocoumarins
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A new acid-catalyzed method for the synthesis of (Z)-3-butylidenephthalides 5 and a novel and general route to 3-alkyl-8-hydroxy/methoxyisocoumarins 6-8 from phthalides 9 is described. The hydroxyphthalides 4 and 10 were obtained by condensation of the phthalide anion with butyraldehyde and acetaldehyde. Reaction of hydroxyphthalides 4 with a mixture of orthophosphoric acid and formic acid gave the (Z)-3-butylidenephthalides 5, while the hydroxyphthalides 4 and 10 on reaction with p-toluenesulfonic acid provided the 3-alkylisocoumarins 6-8. The present approaches permit variation of the 3-substituent in isocoumarin and the pattern of functionalization on the aromatic rings of both isocoumarins and alkylidenephthalides.
- Mali, Raghao S.,Babu, Kantipudi N.
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p. 2488 - 2492
(2007/10/03)
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- A New Procedure for Regiospecific Syntheses of Benzopyran-1-ones
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A new, general route to benzopyran-1-ones 33 from phthalaldehydic acids 27 and nitroalkanes 28 is described.The sequence permits strightforward variation of both the 3-substituent and the pattern of functionalization on the aromatic ring of the benzopyran
- Hauser, Frank M.,Baghdanov, Vaceli M.
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p. 4676 - 4681
(2007/10/02)
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- A Convenient Synthesis of 3-Substituted 8-Methoxy- and 6,8-Dimethoxyisocoumarins
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The reaction of N-methoxy-N-methylamides with the anion of ethyl 2-methoxy-, or 2,4-dimethoxy-6-methylbenzoate gives the corresponding ketones, which are cyclised to give the 3-substituted 8-methoxy- and 6,8-dimethoxyisocoumarins in good overall yield.
- Lewis, Christopher N.,Spargo, Peter L.,Staunton, James
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p. 944 - 946
(2007/10/02)
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- A New Synthesis of some naturally occuring Isocoumarins. 8-Hydroxy-3-methyl-3,4-dihydroisocoumarin (Mellein) and 8-Hydroxy-3-methylisocoumarin
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3-Methyl-8-methoxyisochroman (5a) on oxidation furnishes 3-methyl-8-methoxy-3,4-dihydroisocoumarin (6a), and demethylated with hydriodic acid to 3-methyl-8-hydroxy-3,4-dihydroisocoumarin (mellein) (7a).Treatment of 6a with N-bromosuccinimide followed by refluxing with triethylamine furnishes 3-methyl-8-methoxyisocoumarin (8a) which on demethylation with hydriodic acid yields 3-methyl-8-hydroxyisocoumarin (9a). 5a and 3-methyl-6-methoxyisochroman (5b) obtained by treating 3-(m-methoxyphenyl)propan-2-ol (4) with HCHO/HCl are separated by fractional distillation. 4 is obtained from m-methoxyphenylacetaldehyde (3) by Grignard reaction with methylmagnesium bromide.The aldehyde (3) is obtained from m-methoxybenzaldehyde (1) by Darzens glycidic ester condensation followed by hydrolysis and decarboxylation of the resulting product.
- Sinha, Jawahar,Singh, Ramyan Prasad,Srivastava, Jagdish N.
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p. 907 - 909
(2007/10/02)
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