20312-83-8

Upstream product

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 98-88-4 benzoyl chloride 
• 66185-72-6 7-(phenylcarbonyl)oxy-4-methyl-2H-1-benzopyran-2-one 
• 31005-05-7 7-(phenylcarbonyl)oxy-2H-1-benzopyran-2-one 
• 10387-49-2 7-acetyloxycoumarin 
• 2747-05-9 4-methylumbelliferyl acetate 
• 108-38-3 m-xylene 
• 63411-81-4 benzoyl-resorcinol 
• 7664-93-9 sulfuric acid 
• 141-97-9 ethyl acetoacetate 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 63411-81-4 benzoyl-resorcinol 
• 424807-26-1 (8-benzoyl-4-methyl-2-oxo-2H-chromen-7-yloxy)-acetic acid ethyl ester 
• 859324-18-8 8-benzyl-7-hydroxy-4-methyl-2H-chromen-2-one 
• 859323-68-5 8-benzoyl-3-bromo-7-hydroxy-4-methyl-coumarin 
• 859323-66-3 8-benzoyl-3-chloro-7-hydroxy-4-methyl-coumarin 
• 859324-33-7 8-benzoyl-3,6-dichloro-7-hydroxy-4-methyl-coumarin 
• 86882-63-5 4-methyl-8-(4-nitrobenzoyl)-9-phenylfuro[2,3-h]chromen-2-one 
• 86882-67-9 8-(Biphenyl-4-carbonyl)-4-methyl-9-phenyl-furo[2,3-h]chromen-2-one 
• 86882-66-8 4-methyl-8-(4-methylbenzoyl)-9-phenylfuro[2,3-h]chromen-2-one 
• 86882-65-7 8-(4-chlorobenzoyl)-4-methyl-9-phenylfuro[2,3-h]chromen-2-one 
• 86882-64-6 8-(4-Bromo-benzoyl)-4-methyl-9-phenyl-furo[2,3-h]chromen-2-one 
• 86882-68-0 2-(p-methoxybenzoyl)-7-methyl-3-phenyl-5H-furo<2,3-h><1>benzopyran-5-one 
• 245728-25-0 8-Benzoyl-7-hydroxy-4-methylcoumarin oxime 
• 86882-69-1 2-(p-hydroxybenzoyl)-7-methyl-3-phenyl-5H-furo<2,3-h><1>benzopyran-5-one 

Relevant academic research and scientific papers

An efficient, mild and scalable synthesis of bioactive compounds containing the angelicin scaffold

An efficient, mild and scalable synthesis of angelicin scaffold based compounds was developed. Particularly, the new synthetic route described here circumvents the need for the previously reported key Fries rearrangement step, which uses impractically har

Anti-influenza drug discovery: Structure-activity relationship and mechanistic insight into novel angelicin derivatives

By using a cell-based high throughput screening campaign, a novel angelicin derivative 6a was identified to inhibit influenza A. (H1N1) virus induced cytopathic effect in Madin-Darby canine kidney cell culture in low micromolar range. Detailed structure-activity relationship studies of 6a revealed that the angelicin scaffold is essential for activity in pharmacophore B, while meta-substituted phenyl/2-thiophene rings are optimal in pharmacophore A and C. The optimized lead 4-methyl-9-phenyl-8-(thiophene-2-carbonyl)-furo[2,3-h] chromen-2-one (8g, IC50 = 70 nM) showed 64-fold enhanced activity compared to the high throughput screening (HTS) hit 6a. Also, 8g was found effective in case of influenza A (H3N2) and influenza B virus strains similar to approved anti-influenza drug zanamivir (4). Preliminary mechanistic studies suggest that these compounds act as anti-influenza agents by inhibiting ribonucleoprotein (RNP) complex associated activity and have the potential to be developed further, which could form the basis for developing additional defense against influenza pandemics.

Intermolecular character of the Fris rearrangement in the series of acyloxycoumarins

In the study of the Fris rearrangement in the series of 7-and 4-acyloxycoumarins we obtained certain data indicating intermolecular character of the rearrangement. The Fris rearrangement of a mixture of 7-benzoyloxy-4-metylcoumarin and 7-acetoxycoumarin results in formation of four reaction products in approximately equal molar ratio. Also, four products were obtained in the Fris rearrangement of 7-and 4-acyloxycoumarins in the presence of hydroxycoumarins. The Fris rearrangement of acyloxycoumarins in the presence of m-xylene at acylcoumarin-m-xylene ratio of 1:6 leads to the corresponding hydroxycoumarins and acylated m-xylenes. Intermediate formation of acylium ions was also detected by evolution of carbon monooxide at the Fris rearrangement of 7-pyvaloyloxy-and 7-isobutyryloxy-4-methylcoumarins. A product of intermolecular migration, 3-acetyl-4-hydoxy-6-methylcoumarin, was discovered also in the rearrangement of 4-acetoxycoumarin in the presence of 4-hydoxy-6-methylcoumarin catalyzed by phosphorus oxychloride.

New synthetic procedure for oxazolo[4,5-h]coumarins

Oximes of 8-acyl-7-hydroxycoumarins when treated with excess acetic anhydride in the presence of concentrated sulfuric acid afford oxazolo[4,5-h]coumarins in good yield. Similar treatment without sulfuric acid results in O,N-diacetates of oximes of 8-acyl