51069-84-2

Usage

Uses

Used in Research Applications:
4-CHLORO-3-FORMYL-6-METHYLCOUMARIN& is used as a fluorescent probe for the detection of thiols, which are essential in various biochemical processes and can be indicative of certain conditions or reactions.
Used in Pharmaceutical Industry:
In the synthesis of dyes and pharmaceuticals, 4-CHLORO-3-FORMYL-6-METHYLCOUMARIN& serves as a key intermediate, contributing to the development of new drugs and improving the properties of existing ones.
Used in Scientific Research:
4-CHLORO-3-FORMYL-6-METHYLCOUMARIN& is utilized in various scientific applications, including the study of its potential biological activities such as antioxidant and anti-inflammatory properties, which can lead to advancements in medicine and healthcare.

InChI:InChI=1/C11H7ClO3/c1-6-2-3-9-7(4-6)10(12)8(5-13)11(14)15-9/h2-5H,1H3

Upstream product

• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 140-39-6 1-acetoxy-4-methylbenzene 
• 106-44-5 p-cresol 
• 13252-83-0 4-hydroxy-6-methylcoumarin 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1448308-15-3 (E)-4-chloro-3-((2-(3-chlorophenyl)hydrazono)methyl)-6-methyl-2H-chromen-2-one 
• 1448308-14-2 (E)-4-chloro-6-methyl-3-((2-m-tolylhydrazono)methyl)-2H-chromen-2-one 
• 1448308-13-1 C₁₇H₁₃ClN₂O₂ 
• 1448308-78-8 1-(3-chlorophenyl)-8-methylchromeno[4,3-c]pyrazol-4(1H)-one 
• 1448308-77-7 8-methyl-1-m-tolylchromeno[4,3-c]pyrazol-4(1H)-one 
• 51070-06-5 8-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-one 
• 1448308-23-3 diethyl 3-(4-chloro-6-methyl-2-oxo-2H-chromen-3-yl)-1-(3-chlorophenyl)-1H-pyrazole-4,5-dicarboxylate 
• 1448308-22-2 diethyl 3-(4-chloro-6-methyl-2-oxo-2H-chromen-3-yl)-1-m-tolyl-1H-pyrazole-4,5-dicarboxylate 
• 1448308-21-1 diethyl 3-(4-chloro-6-methyl-2-oxo-2H-chromen-3-yl)-1-phenyl-1H-pyrazole-4,5-dicarboxylate 

Relevant academic research and scientific papers

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.

Sulfonamides containing coumarin moieties selectively and potently inhibit carbonic anhydrases II and IX: Design, synthesis, inhibitory activity and 3D-QSAR analysis

A series of sulfonamides containing coumarin moieties had been prepared that showed a very interesting profile for the inhibition of two human carbonic anhydrase inhibitors. These compounds were evaluated for their ability to inhibit the enzymatic activity of the physiologically dominant isozymes hCA II and the tumor-associated isozyme hCA IX. The most potent inhibitor against hCA II and IX were compounds 5d (IC50 = 23 nM) and 5l (IC50 = 24 nM), respectively. These sulfonamides containing coumarin moieties may prove interesting lead candidates to target tumor-associated CA isozymes, wherein the CA domain is located extracellularly. Eighteen compounds were scrutinized by CoMFA and CoMSIA techniques of 3D quantitative structure-activity relationship. Nine of the compounds were evaluated for cytotoxicity against human macrophage.

Synthesis, anticancer activity and photophysical properties of novel substituted 2-oxo-2H-chromenylpyrazolecarboxylates

2-Oxo-2H-chromenylpyrazolecarboxylates (8a-h and 12a-zb) have been synthesized by [3 + 2] cycloaddition of 2H-chromenophenylhydrazones (7a-h and 11a-w) with diethyl/dimethylbut-2-ynedioates. Phenylchromeno[4,3-c]pyrazol-4(1H) -ones (13i-n) were prepared from corresponding phenylhydrazones (7a-h) with catalytic amount of piperidine in presence of pyridine as a solvent at 100°C. All the synthesized compounds (8a-h, 12a-zb and 13a-n) were screened for anticancer activity against three human cancer cell lines such as prostate (DU-145), lung adenocarcinoma (A549), and cervical (HeLa) by standard MTT assay method. Further, photophysical properties (UV and fluorescence) for these compounds were discussed.

Synthesis of some novel spiro substituted pyrido[2,3-c]coumarins by exploring ‘tertiary amino effect’ reaction strategy

Some novel spiro substituted pyrido[2,3-c]coumarin derivatives were synthesized from 4-hydroxycoumarin by exploring ‘tertiary amino effect’ reaction strategy.

Synthesis and antimicrobial screening of 4H-2-acetyl-3-acetyamido furo[3,2-c] benzopyran 4-one, 11H-2,4-dimethyl-3,4-dihydro-3-amino-4-hydroxy- pyrimido [3,2-d]furo [3,2-c] benzopyran-11-one and 4H-2-acetyl-3-(3′- methyl-1′,2′,4′-triazol-4′-yl) furo[3,2-c] benzopyran 4-one

A suspension of 4H-2-acctyl-3-amino furo [3,2-c] benzopyran 4-onc 5a-d in aqueous sodium hydroxide is treated with acetyl chloride to give 4H-2-acelyl-3-acclylamido furo[3,2-c] benzopyran 4-onc 6a-d. The compounds 6a-d and hydrazine hydrate in absolute alcohol is relluxed to give 11H-2,4-dimethyl-3,4-dihydro-3-amino-4-hydroxy-pyrimido[3,2-d] furo [3,2c]benzopyran-11-one 7a-d which in formic acid is relluxed for 5 hr to give 4H-2-acetyl-3-(3′-methyl-1′,2′,4′-triazol-4′-yl) furo[3.2-c]benzopyran 4-one 8a-d. The structures of all these compounds have been established on the basis of the spectral and analytical data. All compounds have showed good antimicrobial activity.