853927-92-1

Basic information

• Product Name: ethyl 2-oxo-6-phenyl-2H-chromene-3-carboxylate
• Synonyms: ethyl 2-oxo-6-phenyl-2H-chromene-3-carboxylate
• CAS NO: 853927-92-1
• Molecular Weight: 294.307
• Mol File: 853927-92-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: ethyl 2-oxo-6-phenyl-2H-chromene-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-oxo-6-phenyl-2H-chromene-3-carboxylate(853927-92-1)
• EPA Substance Registry System: ethyl 2-oxo-6-phenyl-2H-chromene-3-carboxylate(853927-92-1)

Safety Data

• Hazardous Substances Data: 853927-92-1(Hazardous Substances Data)

Upstream product

• 3702-98-5 ethyl 4,4,4-trichloroacetoacetate 
• 1761-63-3 2-hydroxy-5-phenylbenzaldehyde 
• 1761-61-1 5-bromosalicyclaldehyde 
• 98-80-6 phenylboronic acid 
• 105-53-3 diethyl malonate 
• 2199-90-8 ethyl 6-bromo-2-oxo-2H-chromene-3-carboxylate 
• 54098-94-1 dimethylphenylborane 

Downstream Products

• 73108-75-5 6-phenyl-2H-chromen-2-one 
• 82119-79-7 6-phenylchromone-3-carboxylic acid 

Relevant articles and documents

Condensation of salicylaldehydes with ethyl 4,4,4-trichloro-3-oxobutanoate: A facile approach for the synthesis of substituted 2H-chromene-3-carboxylates

A highly efficient and simple protocol has been developed for the preparation of ethyl 2-oxo-2H-chromene-3-carboxylates 3a-v by the condensation of salicylaldehydes 1a-v with ethyl 4,4,4-trichloro-3-oxobutanoate 2 for the first time. The reaction is proceeding via Knoevenagel pathway followed by a selective addition of the phenolic hydroxyl group to the carbonyl group adjacent to the CCl3 group rather than ester carbonyl due to a strong electron withdrawing effect and produced coumarin derivative 3a with the elimination of CHCl3.

α-Glucosidase inhibitory antihyperglycemic activity of substituted chromenone derivatives

Series of 3,4- and 3,6-disubstituted chromenones including new chromenone derivatives were synthesized applying various synthetic strategies including Pechmann condensation, Knoevenagel condensation, Reimer-Tiemann reaction and Suzuki coupling in very good yields. Synthesized compounds (4a-z) were screened for in vitro α-glucosidase inhibitory and 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activities. Majority of compounds displayed varying degrees of α-glucosidase inhibitory and DPPH scavenging activity. Compound 4x emerged as the most potent α-glucosidase inhibitor in present series of compounds owing to the presence of 3-acetyl-6-(6-methoxy-3-pyridyl) group on chromenone; however, it could not display DPPH scavenging activity and was found to be mixed non-competitive type inhibitor of rat intestinal α-glucosidase. When tested in vivo for antihyperglycemic activity in starch loaded Wistar rats, it displayed significant antihyperglycemic property. This is the first report assigning rat intestinal α-glucosidase inhibitory property for this class of new chromenones and presents new family of compounds possessing α-glucosidase inhibitory activities and antihyperglycemic property. Compound 4x may serve as an interesting new compound for the development of therapeutics targeted against diet-induced hyperglycemia in diabetes.