294875-39-1

Basic information

• Product Name: 7-hydroxy-8-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-4-methyl-2H-chromen-2-one
• Synonyms: 7-hydroxy-8-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-4-methyl-2H-chromen-2-one
• CAS NO: 294875-39-1
• Molecular Formula: C17H22N2O4
• Molecular Weight: 318.36758
• Mol File: 294875-39-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-hydroxy-8-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-4-methyl-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-hydroxy-8-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-4-methyl-2H-chromen-2-one(294875-39-1)
• EPA Substance Registry System: 7-hydroxy-8-((4-(2-hydroxyethyl)piperazin-1-yl)methyl)-4-methyl-2H-chromen-2-one(294875-39-1)

Safety Data

• Hazardous Substances Data: 294875-39-1(Hazardous Substances Data)

Upstream product

• 108-46-3 recorcinol 
• 103-76-4 1-(2-hydroxyethyl)piperazine 
• 50-00-0 formaldehyd 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 

Relevant articles and documents

Novel 8-substituted coumarins that selectively inhibit human carbonic anhydrase IX and XII

A novel series of 8-substituted coumarin-based compounds, characterized by the presence of alkylpiperazine and arylpiperazine chains, were synthesized and tested for their inhibitory activity against four human carbonic anhydrase (hCA) isoforms. All compounds displayed nanomolar potency against the cancer-related hCA IX and hCA XII; moreover, they were shown to be devoid of any inhibitory activity toward the cytosolic hCA I and hCA II up to 10 μM concentration in the assay system. Therefore, the synthesized coumarin ligands demonstrated to be potent and selective hCA IX/XII inhibitors, and were shown to be as potent as the reference inhibitor acetazolamide against hCA XII, with single-digit nanomolar Ki values. Molecular modeling studies provided a rationale for explaining the selectivity profile of these non-classic hCA inhibitors and their interactions with the enzymes, according to their specific mechanism of action, thus paving the way for future structure-based lead optimization studies.

Piperazine and piperidine-substituted 7-hydroxy coumarins for the development of anti-inflammatory agents

Coumarins (2H-1-benzopyran-2-one), derivatives that can be isolated from several plants, have been reported for their anticoagulant, antimicrobial, anti-inflammatory, or anticancer activity. Some of these structures are currently approved for the treatment of cardiovascular diseases, as antibiotics or as an anticancer drug. Given the great potential of this structure and the limited number of studies that focus on molecules derived from carbon 8 of the benzopyranone heterocycle, we synthesized in this project 38 coumarin derivatives by substituting carbon 8 of the benzopyran ring with some aromatic and aliphatically substituted piperidines and piperazines. As a few of these structures were already shown to exhibit some carbonic anhydrase (CA) inhibition and as CA enzymes are reported to be closely related to inflammation, the synthesized derivatives were evaluated for their anti-inflammatory activity in vitro. The results indicated that compounds 20 and 31 revealed promising anti-inflammatory activity, as they demonstrated better activity than the reference drugs.