339062-83-8

Basic information

• Product Name: 2-amino-4-(3-chloro-4,5-dimethoxyphenyl)-3-cyano-7-(dimethylamino)-4H-chromene
• Synonyms: 2-amino-4-(3-chloro-4,5-dimethoxyphenyl)-3-cyano-7-(dimethylamino)-4H-chromene
• CAS NO: 339062-83-8
• Molecular Weight: 385.85
• Mol File: 339062-83-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-amino-4-(3-chloro-4,5-dimethoxyphenyl)-3-cyano-7-(dimethylamino)-4H-chromene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-4-(3-chloro-4,5-dimethoxyphenyl)-3-cyano-7-(dimethylamino)-4H-chromene(339062-83-8)
• EPA Substance Registry System: 2-amino-4-(3-chloro-4,5-dimethoxyphenyl)-3-cyano-7-(dimethylamino)-4H-chromene(339062-83-8)

Safety Data

• Hazardous Substances Data: 339062-83-8(Hazardous Substances Data)

Upstream product

• 18268-68-3 5-chloroveratraldehyde 
• 109-77-3 malononitrile 
• 99-07-0 3-Dimethylaminophenol 

Downstream Products

• 339062-86-1 3-Cyano-7-dimethylamino-2-succinimido-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene 

Relevant articles and documents

Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay. 1. Structure-activity relationships of the 4-aryl group

By applying a novel cell- and caspase-based HTS assay, 2-amino-3-cyano-7- (dimethylamino)-4-(3-methoxy-4,5-methylenedioxyphenyl)-4H-chromene (1a) has been identified as a potent apoptosis inducer. Compound 1a was found to induce nuclear fragmentation and PARP cleavage, as well as to arrest cells at the G2/M stage and to induce apoptosis as determined by the flow cytometry analysis assay in multiple human cell lines (e.g. Jurkat, T47D). Through structure-activity relationship (SAR) studies of the 4-aryl group, a 4- and 7-fold increase in potency was obtained from the screening hit 1a to the lead compounds 2-amino-4-(3-bromo-4,5-dimethoxyphenyl)-3-cyano-7-(dimethylamino) -4H-chromene (1c) and 2-amino-3-cyano-7-(dimethylamino)-4-(5-methyl-3-pyridyl)- 4H-chromene (4e), with an EC50 of 19 and 11 nM in the caspase activation assay in T47D breast cancer cells, respectively. The 2-amino-4-aryl-3-cyano-7-(dimethylamino)-4H-chromenes also were found to be highly active in the growth inhibition MTT assay, with GI50 values in the low nanomolar range for compound 1c. Significantly, compound 1c was found to have a GI50 value of 2 nM in the paclitaxel resistant, p-glycoprotein overexpressed, MESSA/DX5 tumor cells. Functionally, compound 1c was found to be a potent inhibitor of tubulin polymerization and to effectively inhibit the binding of colchicine to tubulin. These results confirm that the cell-based caspase activation assay is a powerful tool for the discovery of potent apoptosis inducers and suggest that the 4-aryl-4H-chromenes have the potential to be developed into future anticancer agents.