19492-02-5

Usage

Uses

Used in Analytical Chemistry:
6-CHLORO-7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE is used as a fluorogenic substrate for the β-glycosidase assay. Its fluorescence properties allow for the development of sensitive and specific detection methods, which are crucial in the analysis of enzymatic activity and related research.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 6-CHLORO-7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE serves as a key compound in the development of novel drugs and drug delivery systems. Its unique chemical structure and optical properties make it a promising candidate for the design of targeted therapies and diagnostic tools.
Used in Biotechnology:
6-CHLORO-7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE is utilized as a marker in biotechnological applications, such as gene expression analysis and protein-protein interaction studies. Its fluorescence allows for the monitoring of biological processes and the identification of potential therapeutic targets.
Used in Environmental Science:
In environmental science, 6-CHLORO-7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE can be employed as a tracer compound for the detection and monitoring of pollutants or contaminants in various ecosystems. Its fluorescence properties enable the tracking of specific substances and the assessment of their impact on the environment.
Used in Material Science:
6-CHLORO-7-HYDROXY-4-METHYL-2H-CHROMEN-2-ONE has potential applications in the development of advanced materials, such as sensors and optoelectronic devices. Its optical properties can be harnessed to create materials with enhanced performance and functionality.

InChI:InChI=1/C10H7ClO3/c1-5-2-10(13)14-9-4-8(12)7(11)3-6(5)9/h2-4,12H,1H3

Upstream product

• 95-88-5 4-Chlororesorcinol 
• 141-97-9 ethyl acetoacetate 
• 7664-93-9 sulfuric acid 
• 5396-89-4 benzyl acetoacetate 

Downstream Products

• 143813-76-7 6-chloro-4-methyl-7-<(2-oxocyclohexyl)oxy>-2H-1-benzopyran-2-one 
• 496784-47-5 7-Allyloxy-6-chloro-4-methyl-chromen-2-one 
• 141536-68-7 8-Allyl-6-chloro-7-hydroxy-4-methyl-chromen-2-one 
• 172739-86-5 6-chloro-4-methyl-2-oxo-2H-1-benzopyran-7-yl phenylcarbamate 

Relevant academic research and scientific papers

Synthesis and structure-activity relationship of coumarins as potent Mcl-1 inhibitors for cancer treatment

Myeloid cell leukemia-1 (Mcl-1) is a validated and attractive target for cancer therapy. Over-expression of Mcl-1 in many cancers allows cancer cells to evade apoptosis and contributes to their resistance to current chemotherapeutics. In this study, more than thirty coumarin derivatives with different substituents were designed and synthesized, and their Mcl-1 inhibitory activities evaluated using a fluorescence polarization-based binding assay. The results showed that the catechol group was a key constituent for Mcl-1 inhibitory activity of the coumarins, and methylation of the catechol group led to decreased inhibitory activity. The introduction of a hydrophobic electron-withdrawing group at the C-4 position of 6,7-dihydroxycoumarin, enhanced Mcl-1 inhibitory capacity, and a hydrophilic group in this position was unbeneficial to the inhibitory potency. In addition, the introduction of a nitrogen-containing group to the C-5 or C-8 position, which allowed an intramolecular hydrogen bond, was also unfavorable for Mcl-1 inhibition. Among all coumarins tested, 4-trifluoromethyl-6,7-dihydroxycoumarin (Cpd 4) displayed the most potent inhibitory activity towards Mcl-1 (Ki = 0.21 ± 0.02 μM, IC50 = 1.21 ± 0.56 μM, respectively), for which the beneficial effect on taxol resistance was also validated in A549 cells. A strong interaction between Cpd 4 and Mcl-1 in docking simulations further supported the observed potent Mcl-1 inhibition ability of Cpd 4. 3D-QSAR analysis of all tested coumarin derivatives further provides new insights into the relationships linking the inhibitory effects on Mcl-1 and the steric-electrostatic properties of coumarins. These findings could be of great value for medicinal chemists for the design and development of more potent Mcl-1 inhibitors for biomedical applications.

Excellent antitumor and antimetastatic activities based on novel coumarin/pyrazole oxime hybrids

A series of hybrids 10a-v based on coumarin/pyrazole oxime have been synthesized, and exhibit good to excellent antitumor activities. Compound 10n has shown remarkable anticancer effect on SMMC-7721 cells (IC50 = 2.08 μM), which is considerably lower than 5-FU (IC50 = 37.8 μM) and similar to ADM (IC50 = 2.67 μM), with little effect on normal hepatic cells LO2. Notably, the suppression experiments of metastatic activities reveal that 10n also displays significant anti-metastasis effects through inhibiting cell migration and invasion in highly metastatic SMMC-7721 cell line, and dose-dependently reverses TGF-β1-induced epithelial-mesenchymal transition (EMT) procedure better than ADM. Finally, 10n also possesses low acute toxicity and potent tumor growth inhibitory property against SMMC-7721 cell lines in vivo. Our findings suggest that novel coumarin/pyrazole oxime hybrids are promising therapeutic agent candidates for further research.

Synthesis and antimycobacterial activity of 1-(β-D-Ribofuranosyl)-4-coumarinyloxymethyl- / -coumarinyl-1,2,3-triazole

A series of β-D-ribofuranosyl coumarinyl-1,2,3-triazoles have been synthesized by Cu-catalyzed cycloaddition reaction between azidosugar and 7-O-/7-alkynylated coumarins in 62–70% overall yields. The in vitro antimycobacterial activity evaluation of the s

Microwave-assisted Synthesis and antifungal activity of coumarin[8,7-e][1,3]oxazine derivatives

The synthesis of novel coumarin[8,7-e][1,3]oxazine derivatives through a microwave-assisted three-component one-pot Mannich reaction is described in this study. All the target compounds were evaluated in vitro for their antifungal activity against Botryti

Synthesis and evaluation of a series of 6-chloro-4-methylumbelliferyl glycosides as fluorogenic reagents for screening metagenomic libraries for glycosidase activity

Screening of large enzyme libraries such as those derived from metagenomic sources requires sensitive substrates. Fluorogenic glycosides typically offer the best sensitivity but typically must be used in a stopped format to generate good signal. Use of fluorescent phenols of pKa 7, such as halogenated coumarins, allows direct screening at neutral pH. The synthesis and characterisation of a set of nine different glycosides of 6-chloro-4-methylumbelliferone are described. The use of these substrates in a pooled format for screening of expressed metagenomic libraries yielded a "hit rate" of 1 in 60. Hits were then readily deconvoluted with the individual substrates in a single plate to identify specific activities within each clone. The use of such a collection of substrates greatly accelerates the screening process.

Novel coumarin isoxazoline derivatives: Synthesis and study of antibacterial activities

A highly efficient and mild protocol for the syntheses of ethyl-3-[7-benzyloxy-4-methyl-2-oxo-2H-8-chromenyl]-5-aryl-4,5-dihydro-4-isoxazole carboxylates and ethyl-3-[7-benzyloxy-3-chloro-4-methyl-2-oxo-2H-8-chromenyl]-5-aryl-4,5-dihydro-4-isoxazole carboxylates in good yields via [3 + 2] cycloaddition of in situ–generated nitrile oxides from 7-benzyloxy-4-methyl-coumarin hydroxymoylchlorides and 7-benzyloxy-3-chloro-4-methyl-coumarin hydroxymoylchlorides respectively with ethyl-3-aryl prop-2-enoate has been developed. The new compounds are screened for antibacterial activity.

A new strategy for synthesis of 9-benzoyl-4-methylpyrano[2,3-f]chromene-2,8-dione using L-proline as a novel and efficient catalyst

We report the high yield synthesis of novel 9-benzoyl-4-methylpyrano[2,3-f]chromene-2,8-dione derivatives obtained by the reaction of 8-formyl-7-hydroxy-4-methylcoumarin with various active methylene compounds. A mechanism of the tandem Knoevenagel condensation and cyclisation reaction is proposed. Structures of all compounds were elucidated on the basis of 1H and 13C NMR, and mass spectrometry, and elemental analysis.

IRE-1α INHIBITORS

PROBLEM TO BE SOLVED: To provide compounds which directly inhibit inositol requiring enzyme 1 (IRE-1α activity) in vitro, prodrugs, and pharmaceutically acceptable salts thereof. SOLUTION: The present invention provides a compound represented by formula (A) [R3 and R4 are H or the like; Q5-Q8, together with the benzene ring to which they are attached, form a benzofused ring, where at least one of Q5-Q8 is a heteroatom selected from N, O, and S. COPYRIGHT: (C)2016,JPOandINPIT

Synthesis and nematicidal bioevaluation of substituted 2H-1-benzopyrane-2- ones and their carbamate derivatives against root-knot nematode (Meloidogyne javanica)

Synthesis of 7-hydroxy-4,5-methyl/7-hydroxy-4-methyl/7,8-dihydroxy-4- methyl/6-chloro-7-hydroxy-4-methyl-2H-1-benzopyrane-2-ones (VI-IX) have been carried out by Pechmann reaction. The condensation of synthesized 2H-1-benzopyran-2-ones (VI-X) with phenyl isocyanate (XI) gave 4,5-methyl/4-methyl/4-methyl/6-chloro-4-methyl-2-oxo-2H-benzopyran-7yl/7,8-diyl/ 4-yl/phenyl carbamates (XIIXVI). The synthesized compounds were characterized on the basis of analytical and spectral data. All the compounds were evaluated for their nematicidal activity in vitro against second stage juveniles (J2) of root-knot nematode (Meloidogyne javanica).

Synthesis, characterization and antibacterial study of 7-O-substituted derivatives of chlorinated Coumarin

In this research work, a series of 7-O-alkyl/aralkyl/acyl substituted derivatives of chlorinated coumarin was synthesized and screened for their antibacterial activity. The parent compound 6-chloro-7-hydroxy-4-methyl-2H- chromen-2-one (3) was prepared by