33265-12-2

Basic information

• Product Name: 3-Hydroxy-7-methoxy-2H-1-benzopyran-2-one
• Synonyms: 3-Hydroxy-7-methoxy-2H-1-benzopyran-2-one
• CAS NO: 33265-12-2
• Molecular Formula: C₁₀H₈O₄
• Molecular Weight: 0
• Mol File: 33265-12-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Hydroxy-7-methoxy-2H-1-benzopyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-7-methoxy-2H-1-benzopyran-2-one(33265-12-2)
• EPA Substance Registry System: 3-Hydroxy-7-methoxy-2H-1-benzopyran-2-one(33265-12-2)

Safety Data

• Hazardous Substances Data: 33265-12-2(Hazardous Substances Data)

Upstream product

• 33259-31-3 7-methoxy-3-aminocoumarin 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 33259-45-9 N-(7-methoxy-2-oxo-2H-chromen-3-yl)acetamide 
• 856202-31-8 C₁₉H₁₅NO₅ 

Downstream Products

• 1416162-80-5 C₂₂H₂₃NO₄ 

Relevant articles and documents

Inhibition of iNOS by Benzimidazole Derivatives: Synthesis, Docking, and Biological Evaluations

Background: Inducible nitric Oxide Synthase (iNOS) plays a key role in the progression of inflammatory diseases by accelerating the production of NO, which makes it an intriguing target to treat inflammation in complex diseases. Therefore, the search is on to develop molecules as selective iNOS inhibitors. Objective: The present work was aimed to design, synthesize and evaluate benzimidazole-coumarin coupled molecules as anti-iNOS agents through in silico and pharmacological studies. Methods: A critical study of literature reports on iNOS inhibitors led to the selection of a (un)substituted coumarin nucleus, 2-aminobenzimidazole, and a 4-atom linker as important structural components for iNOS inhibition. Two series of compounds (7-16 and 17-26) were designed and synthesized by coupling these components. The compounds were subjected to docking using iNOS (1QW4) and nNOS (1QW6) as targets. All compounds were evaluated for NO and iNOS inhibitory activities in vitro. The selected compound was finally evaluated for anti-inflammatory activity in vivo using the carrageenan-induced rat paw edema model. Results: All compounds showed moderate to good inhibition of NO and iNOS in vitro. Compound 12 was the most potent inhibitor of NO and iNOS. Hence, it was evaluated in vivo for toxicity and anti-inflammatory activity. It was found to be safe in acute toxicity studies, and effective in reducing the rat paw edema significantly. Its anti-inflammatory behaviour was similar to that of aminoguanidine, which is a selective iNOS inhibitor. Conclusion: The newly synthesized benzimidazole-coumarin hybrids may serve as potential leads for the development of novel anti-iNOS agents.

Toward the development of dual-targeted glyceraldehyde-3-phosphate dehydrogenase/ trypanothione reductase inhibitors against trypanosoma brucei and trypanosoma Cruzi

A significant improvement in the treatment of trypanosomiases has been achieved with the recent development of nifurtimox- eflornithine combination therapy (NECT). As an alternative to drug combinations and as a means to overcome most of the antitrypanosomatid drug discovery challenges, a multitarget drug design strategy has been envisaged. To begin testing this hypothesis, we designed and developed a series of quinone-coumarin hybrids against glyceraldehyde-3-phosphate dehydrogenase/trypanothione reductase (GAPDH/TR). These enzymes belong to metabolic pathways that are vital to Trypanosoma brucei and Trypanosoma cruzi, and have thus been considered promising drug targets. The synthesized molecules were characterized for their dual-target antitrypanosomal profile, both in enzyme assays and in in vitro parasite cultures. The merged derivative 2-{[3-(3-dimethylaminopropoxy)- 2-oxo-2H-chromen-7-yl]oxy}anthracene- 1,4-dione (10) showed an IC50 value of 5.4 mm against TbGAPDH and a concomitant Ki value of 2.32 mm against TcTR. Notably, 2-{4-[6-(2-dimethylaminoethoxy)- 2-oxo-2H-chromen-3-yl]phenoxy}anthracene-1,4- dione (compound 6) displayed a remarkable EC50 value for T. brucei parasites (0.026 mm) combined with a very low cytotoxicity toward mammalian L6 cells (7.95 mm). This promising low toxicity of compound 6 might be at least partially due to the fact that it does not interfere with human glutathione reductase.

Reaction of aryl-2-hydroxypropenoic derivatives with boron tribromide

(Z)-Mono, di or trimethoxyphenyl-2-hydroxypropenoic acids 1a-d gave mixtures of (E) and (Z) mono, di or trihydroxyphenyl-2-hydroxypropenoic acids 2a-d when treated with boron tibromide. The isomerisation proceeds during the work-up and depends on the duration of the hydrolysis and the number of oxygens on the aromatic ring. When the aromatic ring was substituted with a methoxy group at the ortho position, a cyclisation occurs, and 3-hydroxycoumarins 3 and benzofuran-2-carboxylic acids 4 can be obtained. 3-Hydroxycoumarin 3a can also be obtained almost quatitatively from the reaction of methyl 3-(2-methoxyphenyl)-2,3-epoxypropanoate with boron tribromide.