24238-62-8

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 2555-37-5 3-acetyl-4-hydroxychromen-2-one 

Downstream Products

• 1383922-95-9 (2Z)-2-(3,4,5-trimethoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383922-99-3 (2Z)-2-(2-hydroxy-3-methoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383923-03-2 (2Z)-2-(6-chloro-2,4-dimethoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383923-07-6 (2Z)-2-(5-bromo-2-methoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383923-10-1 (2Z)-2-[4-(dimethylamino)benzylidene]-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383923-13-4 (2Z)-2-(3-chlorobenzylidene)-4H-furo[3,2-c]chromene3,4(2H)-dione 
• 1383923-16-7 (2Z)-2-(2,4-dimethoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383923-27-0 (2E,2'Z)-2'-(5'-bromo-2'-hydroxybenzylidene)-4H,4'H-2,3'-bifuro[3,2-c]chromenylidene-3,4,4'-trione 
• 1383922-72-2 (2Z)-2-benzylidene-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383922-79-9 (2Z)-2-(2-chlorobenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383922-83-5 (2Z)-2-(4-nitrobenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383922-87-9 (2Z)-2-(4-methoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 1383922-91-5 (2Z)-2-(3-bromo-4-methoxybenzylidene)-4H-furo[3,2-c]chromene-3,4(2H)-dione 
• 944548-93-0 2-hydroxy-4-[4-(4-hydroxy-2-oxo-2H-chromen-3-yl)thiazol-2-ylamino]benzoic acid 

Relevant academic research and scientific papers

Hantzsch reaction of 3-(2-bromoacetyl)-4-hydroxy-chromen-2-one. Synthesis of 3-(thiazol-4-yl)-4-hydroxy coumarines

3-Acetyl-4-hydroxy-chromen-2-one (1) was brominated with phenyltrimethylammonium tribromide to afford 3-(2-bromoacetyl)-4-hydroxy- chromen-2-one (2) whose reactions with thiourea, thioacetamide and ammonium dithiocarbamate gave respectively 3-(2-amino-thiazol-4-yl)-4-hydroxy-, 4-hydroxy-3-(2-phenyl-thiazol-4-yl)- and 4-hydroxy-3-(2-mercapto-thiazol-4-yl) chromen-2-one. In a similar manner, compound 2 was treated with four 1-substituted-2-thioureas and thiobenzamide to give the corresponding 4-hydroxy-3-(thiazol-4-yl)-chromen-2-one derivatives.

Biochemical and pharmacological evaluation of 4-hydroxychromen-2-ones bearing polar C-3 substituents as anticoagulants

The objective of this study was to investigate in vitro and in vivo anticoagulant activity of sixteen 4-hydroxycoumarin derivatives bearing polar C-3 scaffolds. The activity was evaluated by measuring prothrombin time. Enhanced anticoagulant activity in vitro was observed for all tested compounds. Upon successive administration of 0.5 mg/kg of body weight to adult Wistar rats, over a period of five days, four derivatives (2b, 4c, 5c and 9c) presented anticoagulant activity in vivo. The most active compound was 2b, with PT = 30.0 s. Low or non-toxic effects in vivo were determined based on the catalytic activity of liver enzymes and the concentration of bilirubin, iron and proteins. Metabolic pathways of the most active compounds in vivo were determined after GC/MS analysis of collected rat urine samples. The excretion occurs by glucuronidation of 7-hydroxy forms of tested derivatives. In vivo results were described using PLS-based CoMFA and CoMSIA 3D-QSAR studies, which showed CoMFA-SE (q2 = 0.738) and CoMSIA-SEA (q2 = 0.763) to be the statistically most relevant models. Furthermore, molecular docking and DFT mechanistic studies performed on the rat VKORC1 homology model revealed interactions between the 4-OH coumarin group in the form of phenolic anion and the Cys135 catalytic site in the transition state.

Structure and condensation reactions of 2,3-dihydrofuro[3,2-c]coumarin-3- one

2,3-Dihydrofuro[3,2-c]coumarin-3-one was synthesized in quantitative yield from 3-(ffl-bromoacetyl)-4-hydroxycoumarin in the presence of nucleophiles (including solvents). This compound undergoes keto-enol tautomerization and easily reacts with aromatic and hetero-aromatic aldehydes to form crotonization products having a Z configuration and exhibiting strong fluorescence.