1983-81-9

Usage

Uses

Used in Pharmaceutical Industry:
4,7-Dihydroxycoumarin is used as a pharmaceutical compound for its diverse biological activities. It is valued for its anti-inflammatory properties, making it a potential candidate for the treatment of inflammation-related conditions. Additionally, its anticancer properties suggest its use in the development of cancer therapeutics, targeting various types of cancer cells. Furthermore, its antidiabetic properties indicate its potential application in managing diabetes and related metabolic disorders.
Used in Cosmetic Industry:
In the cosmetic industry, 4,7-Dihydroxycoumarin is used as an active ingredient in skincare products for its anti-inflammatory and antioxidant properties. It can help soothe irritated skin, reduce redness, and protect the skin from oxidative stress caused by environmental factors.
Used in Research Applications:
4,7-Dihydroxycoumarin is used as a research compound in various scientific studies, particularly in the fields of pharmacology, biochemistry, and molecular biology. It serves as a valuable tool for understanding the mechanisms of action of coumarin-based compounds and their potential applications in medicine and other industries.

InChI:InChI=1/C9H6O4/c10-5-1-2-6-7(11)4-9(12)13-8(6)3-5/h1-4,10-11H

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 201230-82-2 carbon monoxide 
• 244049-27-2 4-amino-7-hydroxy-2H-chromen-2-one 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 29682-12-0 1-[4-(benzyloxy)-2-hydroxyphenyl]ethanone 
• 30992-66-6 4-hydroxy-7-(phenylmethoxy)-2H-1-benzopyran-2-one 
• 108-46-3 recorcinol 
• 141-82-2 malonic acid 
• 17575-15-4 4-hydroxy-7-methoxycoumarine 

Downstream Products

• 112222-66-9 (4,7-dihydroxy-2-oxo-2H-chromen-3-yl)-(4-hydroxy-2-oxo-2H-chromen-3-yl)-acetic acid ethyl ester 
• 109650-25-1 7-hydroxy-4-(4-methoxy-benzoyloxy)-coumarin 
• 1661-60-5 2-[4-(4,7-dihydroxy-2-oxo-2H-chromen-3-yl)-buta-1,3-dienyl]-3-methyl-4-phenyl-thiazolium betaine 
• 1661-56-9 2-[2-(4,7-dihydroxy-2-oxo-2H-chromen-3-yl)-vinyl]-3-methyl-4-phenyl-thiazolium betaine 
• 34173-06-3 6-Hydroxy-1,2-benzisoxazole-3-acetic acid 
• 129207-41-6 3-benzoylamino-8-hydroxy-2H,5H-pyrano<3,2-c><1>benzopyran-2,5-dione 
• 98411-91-7 5-(2,4-Dihydroxy-phenyl)-2-methyl-2,4-dihydro-pyrazol-3-one 
• 65692-17-3 4-methoxy-7-hydroxy-2H-chromen-2-one 
• 113138-99-1 Acetic acid 7-acetoxy-3-(2,5-diacetoxy-phenyl)-2-oxo-2H-chromen-4-yl ester 
• 113138-98-0 4,7-dihydroxy-3-(2',5'-dihydroxyphenyl)coumarin 
• 75590-61-3 1-benzyl-4-[3-(4-hydroxy-3-nitrocoumarin-7-yloxy)propyl]piperazine 
• 75590-51-1 1-(4-chlorobenzyl)-4-[2-(4-hydroxy-3-nitrocoumarin-7-yloxy)ethyl]piperazine 
• 75590-60-2 7-[3-(4-Benzyl-piperazin-1-yl)-propoxy]-4-hydroxy-chromen-2-one; hydrochloride 
• 75590-50-0 7-{2-[4-(4-Chloro-benzyl)-piperazin-1-yl]-ethoxy}-4-hydroxy-chromen-2-one; hydrochloride 

Relevant academic research and scientific papers

Synthesis of osthole derivatives with grignard reagents and their larvicidal activities on mosquitoes

The structure of osthole has been modified to improve its larvicidal activity against mosquitoes. A new efficient synthesis of osthole derivatives with Grignard reagents has been developed, which employs CuI and LiCl as promoters and covers a broad range of substrates to afford the corresponding products in mild to good yields (up to 83%). Bio-activity evaluation showed that several products exhibited better activities than osthole. CuI and LiCl promoted efficient synthesis of osthole derivatives with Grignard reagents has been developed. Bio-activity evaluation showed that several products exhibited far better larvicidal activities against mosquitoes than osthole.

Synthesis and biological evaluation of novel 4,7-dihydroxycoumarin derivatives as anticancer agents

A series of novel 4,7-dihydroxycoumarin based acryloylcyanohydrazone derivatives were synthesized and evaluated for antiproliferative activity against four different cancer cell lines (A549, HeLa, SKNSH, and MCF7). Most of the compounds displayed potent c

Synthesis and characterization of some coumarins with two hydroxy or methoxy substituents

The first synthesis of the 6-hydroxy-4-methoxycoumarin (5) was carried out in 25% overall yield from 6-methoxy-4-hydroxycoumarin (1) by hydrolysis of the methoxy group and subsequent selective methylation of the hydroxyl group at position 4. The 1H and 13C NMR data of compounds 1-6 are reported.

Synthesis and cytotoxic activities of novel 4-methoxy-substituted and 5-methyl-substituted (3′S,4′S)-(-)-cis-khellactone derivatives that induce apoptosis via the intrinsic pathway

This study deals with the design and synthesis of a series of novel 4-methoxy-substituted and 5-methyl-substituted (3′S,4′S)-(-)-cis-khellactones. The newly synthesized compounds were characterized by1H nuclear magnetic resonance (NMR),13

Lysosome-targeted Cys near-infrared fluorescent probe and preparation method and application thereof

The invention belongs to the technical field of analysis and detection, and provides a lysosome-targeted Cys near-infrared fluorescent probe and a preparation method and application thereof. The near-infrared fluorescent probe is 3-(2-(3-(dicyanomethylene

Design, synthesis, biological and in silico evaluation of coumarin-hydrazone derivatives as tubulin targeted antiproliferative agents

Coumarin-based different series of hydrazone derivatives were synthesized and evaluated for anticancer activity against four different human cancer cell lines. The activity of the compounds were compared with doxorubicin as a standard drug and all the compounds exhibited good to moderate cytotoxicity with IC50 values ranging from 6.07 to 60.45 μM against all the examined cancer cell lines. Based on the screening results, it was concluded that the compounds 12a and 18a were the most promising medicinal entities. In vitro tubulin polymerisation inhibition assay was performed for the compounds 12a and 18a and these two compounds displayed good potency when compared with colchicine as the standard drug. The interaction of these compounds with tubulin protein was also studied with the help of molecular docking technique using Discovery studio software. Furthermore, the molecular and ADMET properties of the compounds were computed with Osiris property software and PreADMET server. The compounds exhibited exciting in vitro and in silico results. Hence we propose that the compounds 12a and 18a could be developed as tubulin targeted potential antiproliferative agents.

Multi-target tacrine-coumarin hybrids: Cholinesterase and monoamine oxidase B inhibition properties against Alzheimer's disease

A series of novel tacrine-coumarin hybrids were designed, synthesized and evaluated as multi-target agents against Alzheimer's disease. The biological assays indicated that most of compounds displayed potent inhibitory activity toward AChE and BuChE, and clearly selective inhibition for MAO-B. Among these compounds, 14c exhibited strong inhibitory activity for AChE (IC50 values of 33.63 nM for eeAChE and 16.11 nM for hAChE) and BuChE (IC50 values of 80.72 nM for eqBuChE and 112.72 nM for hBuChE), and the highest inhibitory activity against hMAO-B (IC50 value of 0.24 11/4M). Kinetic and molecular modeling studies revealed that 14c was a mixed-type inhibitor, binding simultaneously to catalytic, peripheral and mid-gorge sites of AChE. It was also a competitive inhibitor, which covered the substrate and entrance cavities of MAO-B. Moreover, 14c could penetrate the CNS and show low cell toxicity. Overall, these results suggested that 14c might be an excellent multi-target agent for AD treatment.

Defining a minimum pharmacophore for simocyclinone D8 disruption of DNA gyrase binding to DNA

The increasing occurrence of drug-resistant bacterial infections in the clinic has created a need for new antibacterial agents. Natural products have historically been a rich source of both antibiotics and lead compounds for new antibacterial agents. The natural product simocyclinone D8 (SD8) has been reported to inhibit DNA gyrase, a validated antibacterial drug target, by a unique catalytic inhibition mechanism of action. In this work, we have used a deconstruction-reconstruction approach to prepare analogs of the coumarin subunit of SD8 and evaluated their ability to disrupt binding of the DNA gyrase enzyme to DNA in a surface plasmon resonance assay. This has led to a minimum pharmacophore required for disruption of binding. Springer Science+Business Media 2014.

Design, synthesis and evaluation of novel tacrine-coumarin hybrids as multifunctional cholinesterase inhibitors against Alzheimer's disease

A series of tacrine-coumarin hybrids (8a-t) were designed, synthesized and evaluated as multifunctional cholinesterase (ChE) inhibitors against Alzheimer's disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit ChE and self-induced β-amyloid (Aβ) aggregation, and to act as metal chelators. Especially, 8f displayed the greatest ability to inhibit acetylcholinesterase (AChE, IC50 = 0.092 μM) and Aβ aggregation (67.8%, 20 μM). It was also a good butyrylcholinesterase inhibitor (BuChE, IC50 = 0.234 μM) and metal chelator. Besides, kinetic and molecular modeling studies indicated that 8f was a mixed-type inhibitor, binding simultaneously to active, peripheral and mid-gorge sites of AChE. These results suggested that 8f might be an excellent multifunctional agent for AD treatment.

Energy transfer in coumarin-sensitised lanthanide luminescence: Investigation of the nature of the sensitiser and its distance to the lanthanide ion

A series of lanthanide complexes [Ln(dpxCy)3]3- have been synthesised. The ligands are composed of a coordinating dipicolinic acid backbone decorated with a polyoxyethylene arm fitted with a coumarin moiety at its extremity. The nature of the coumarin as well as the length of the linker have been varied. Upon excitation at 320 nm, the coumarin exclusively acts as an antenna while the dipicolinic acid core is not excited. Upon excitation below 300 nm, both parts are excited. With europium as a metal centre, the relaxation of the europium ion (intrinsic quantum yield ΦEuEu and radiative lifetime τr) is constant for all the studied ligands. Therefore, the observed differences in overall quantum yield (ΦEuL) in such systems come exclusively from the variation of the terminal coumarin. The overall quantum yields of the studied complexes are low (ΦEuL sens), the distance between the coumarin sensitiser and the lanthanide centre was explored in solution and compared to the solid state. In the solid state, a dramatic effect was confirmed, with an improvement of 80% in the quantum yield ΦEuL for short linkers ((-CH2CH2O-)n with n = 1 compared to n = 3). By monitoring the lifetime decay of the excited state of the lanthanide cation with nanosecond vs. microsecond time-resolved spectroscopy at low temperature, the sensitisation of the lanthanide ions by coumarin derivatives was demonstrated to mainly occur through the singlet excited state of the coumarin and not via the usual triplet pathway. No evidence of a different behaviour at room temperature was found by transient triplet-triplet absorption spectroscopy.