13252-83-0

Usage

Uses

Used in Chemical Synthesis:
4-Hydroxy-6-methylcoumarin is used as a chemical intermediate for the in situ generation of α-methylenechromanes, α-methylenequinoline, and ortho-quinone methides via the Knoevenagel reaction. This application is valuable in the synthesis of various complex organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Hydroxy-6-methylcoumarin is used as a key component in the preparation of 8-methyl-2-phenyl-4H-furo-[3,2-c]benzopyran-4-one and 6-methyl-2-phenyl-4H-furo-[2,3-b]benzopyran-4-one. These compounds have potential applications in the development of new drugs and therapeutic agents.
Used in Research and Development:
4-Hydroxy-6-methylcoumarin is also utilized in research and development settings, where it serves as a valuable compound for studying its chemical properties and exploring its potential uses in various industries, including pharmaceuticals, materials science, and chemical engineering.

InChI:InChI=1/C10H8O3/c1-6-2-3-9-7(4-6)8(11)5-10(12)13-9/h2-5,11H,1H3

Upstream product

• 7446-70-0 aluminium trichloride 
• 104-93-8 p-methylanizole 
• 98-95-3 nitrobenzene 
• 1663-67-8 malonoyl dichloride 
• 152894-72-9 2-trichloromethyl-6-methylchromone 
• 106-44-5 p-cresol 
• 141-82-2 malonic acid 
• 60179-39-7 3-(4-methylphenoxy)-3-oxo-propanoic acid 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 105-58-8 Diethyl carbonate 
• 140-39-6 1-acetoxy-4-methylbenzene 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 288087-80-9 (Z)-3-Amino-4,4,4-trichloro-1-(2-hydroxy-5-methyl-phenyl)-but-2-en-1-one 
• 15014-23-0 di-p-methylphenyl malonate 

Downstream Products

• 103162-77-2 SKI-190986 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 74700-73-5 7,10-dihydroxy-9-methoxy-6-(4-methoxyphenyl)-3-methyl-6H,11H-<2>benzopyrano<4,3-c><1>benzopyran-11-one 
• 98411-89-3 5-(2-Hydroxy-5-methyl-phenyl)-2-methyl-2,4-dihydro-pyrazol-3-one 
• 108305-83-5 6-methyl-4-(1,2-diphenyl-2-oxoethyloxy)coumarin 
• 2555-37-5 3-acetyl-4-hydroxychromen-2-one 
• 41773-41-5 6-methyl-3-acetyl-4-hydroxy-2H-benzopyran-2-one 
• 126214-23-1 4-hydroxy-6-methyl-2-oxo-2H-1-benzopyran-3-carboxaldehyde 

Relevant academic research and scientific papers

Design, synthesis and antifungal activity of coumarin ring-opening derivatives

Based on our initial design, we synthesized two series of coumarin ring-opening derivatives by the reactions of hydrolysis and methylation. Results of antifungal screening in vitro showed that the target compounds exhibited potent activity against the six

A regioselective synthesis of pentacyclic compounds containing coumarin, pyrrole, indene without catalysts under microwave irradiation

A concise and efficient approach was developed for the synthesis of pentacyclic compounds containing coumarin, pyrrole, indene in a regioselective manner in good yields via the reactions of N-substituted 4-aminocoumarin compounds and ninhydrin using micro

Electrochemical Sulfenylation of 4-Hydroxycoumarins with Aryl Thiols Catalyzed by Potassium Iodide

A KI-catalyzed indirect electrochemical oxidative method for the synthesis of sulfenylated 4-hydroxycoumarins via cross-coupling of 4-hydroxycoumarins and aryl thiols at a low potential has been reported. The electrocatalytic activity of KI for sulfenylat

Copper(II)-Catalyzed Tandem Reaction: Synthesis of Furo[3,2- c]coumarin Derivatives and Evaluation for Photophysical Properties

An efficient protocol for synthesizing furo[3,2-c]coumarin derivatives is described. The novel reaction could afford the desired furocoumarins with good to excellent yields in a mild and rapid manner. Large substrate scope screening and scale-up preparation have also been accomplished, and selected compounds were evaluated for their photophysical properties.

Synthesis, characterization, and anticoagulant activity of new functionalized biscoumarins

Despite their rarity and structural complexity, natural and synthetic biscoumarins have polarized much attention from investigators particularly due to their characteristic activity as anticoagulant agents. In this work, a panel of twelve functionalized biscoumarins was synthesized in two schematic steps; the first one started by condensing various phenol-based derivatives with malonic acid via a Pechmann-type reaction yielding alkyl-substituted 4-hydroxycoumarins herein symbolized as (E1-E12). The latter compounds were undergone a self-coupling under the influence of methylene iodide to afford the target functionalized biscoumarins, which were symbolized as (EY1-EY12). The potential of the synthesized biscoumarins as anticoagulant applicants was investigated in vivo using rabbit as an animal model. The employed assay was the prothrombin time that was monitored after three and five days of the last oral treatment. The results gathered from this test revealed that the synthesized biscoumarins have a promising anticoagulant activity compared with warfarin as a standard anticoagulant drug, with privileged influence contributed to those substituted at position 7 of the coumarin framework. The authors concluded that the substitution of an alkyl group at that position of the coumarin monomer may intensify the anticoagulant activity of the prepared biscoumarins. Also, this intensity was directly proportionated to the increase in the molecular weight of this alkyl group. Accordingly, the synthesized biscoumarins possessing this property would provide an efficient base for synthesizing new compounds, which have a promising anticoagulant effect.

Synthesis and anti-inflammatory activity of 2-oxo-2H-chromenyl and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates

Cycloaddition reaction of 4-chloro-2-oxo-2H-chromene-3-carbaldehydes (3a-g) and 4-chloro-2H-chromene-3-carbaldehydes (7a-h) with activated alkynes (4a-b) provided the 2-oxo-2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (5a-n) and 2H-chromenyl-5-oxo-2,5-dihydrofuran-3-carboxylates (8a-p). All the prepared compounds were screened for anti-inflammatory activity. In vitro anti-inflammatory activity data demonstrated that the compounds 5g, 5i, 5k-l and 8f are effective among the tested compounds against TNF-α (1.108 ± 0.002, 0.423 ± 0.022, 0.047 ± 0.001, 0.070 ± 0.002 and 0.142 ± 0.001 μM) in comparison with standard compound Prednisolone (0.033 ± 0.002 μM). Based on in vitro results, three compounds (5i, 5k and 8f) have been selected for in vivo experiments and these compounds are identified as better compounds with respect to anti-inflammatory activity in LPS induced mice model. Compound 5i was identified as potent and showed significant reduction in TNF-α and IL-6.

Synthesis and biological evaluation of bis-N2,N2′-(4-hydroxycoumarin-3-yl)ethylidene]-2,3-dihydroxysuccinodihydrazides

A series of N2,N2′-bis[4-hydroxycoumarin-3-yl)ethylidene]-2,3-dihydroxysuccino-hydrazides, containing 4-hydroxycoumarin, hydrazine and tartaric acid moieties, have been prepared and examined for possible biological activity. Several of these compounds exhibit promising HIV-1 integrase inhibition (IC50 = 3.5 μM), and anti-T. brucei (32% viability) and anti-mycobacterial (Visual MIC90 = 15.63 μM) activity.

Regioselective Synthesis of 4,5-Dihydro-6H-oxepino[3,2-c]chromene-2,6(3H)-diones through Palladium-Catalyzed Intramolecular Alkoxycarbonylation of 3-Allyl-4-hydroxycoumarins

Seven-membered ring lactones fused to coumarin scaffolds were obtained via a palladium-catalyzed regioselective intramolecular alkoxycarbonylation under a CO atmosphere. Cyclocarbonylation of 3-allyl-4-hydroxycoumarin derivatives was accessed in the absen

Novel conjugates of podophyllotoxin and coumarin: Synthesis, cytotoxicities, cell cycle arrest, binding CT DNA and inhibition of Topo IIβ

A series of conjugates of podophyllotoxin and coumarin were prepared using the click reaction, and their cytotoxicities against A549, HepG2, HeLa, and LoVo cells were evaluated. Among them, compound 14e exhibited the strongest cytotoxicities against these cancer cells with IC50 values of 4.9–17.5 μM. Furthermore, 14e disrupted microtubules and induced cell cycle arrest at G1 phase by regulating P21 and Cyclin D1 in LoVo cells. In addition, 14e bond CT DNA and selectively inhibited Topo IIβ over Topo IIα. Molecular docking model showed that 14e appeared to form stable hydrogen bonds with several DNA bases and residue Gln778. Taken together, these conjugates have the potential to be developed as anti-tumor drugs.

Design, synthesis, and mechanism of dihydroartemisinin-coumarin hybrids as potential anti-neuroinflammatory agents

Cancer patients frequently suffer from cancer-related fatigue (CRF), which is a complex syndrome associated with weakness and depressed mood. Neuroinflammation is one of the major inducers of CRF. The aim of this study is to find a potential agent not only on the treatment of cancer, but also for reducing CRF level of cancer patients. In this study, total-thirty new Dihydroartemisinin-Coumarin hybrids (DCH) were designed and synthesized. The in vitro cytotoxicity against cancer cell lines (HT-29, MDA-MB-231, HCT-116, and A549) was evaluated. Simultaneously, we also tested the anti-neuroinflammatory activity of DCH. DCH could inhibit the activated microglia N9 release of NO, TNF-α, and IL-6. The docking analysis was shown that MD-2, the coreceptor of TLR4, might be one of the targets of DCH.