53653-66-0

Usage

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

Upstream product

• 141-97-9 ethyl acetoacetate 
• 635-93-8 5-chlorosalicyclaldehyde 
• 5977-14-0 acetoacetamido 
• 81375-98-6 4,4-bis(ethylsulfanyl)but-3-en-2-one 
• 674-82-8 4-methyleneoxetan-2-one 
• 105-45-3 acetoacetic acid methyl ester 
• 626-34-6 ethyl aminocrotonate 
• 2420-26-0 4-chlorosalicylaldehyde 

Downstream Products

• 106577-99-5 3-(2-bromoacetyl)-6-chloro-2H-chromen-2-one 
• 228854-68-0 propionic acid N'-[4-(6-chloro-2-oxo-2H-chromen-3-yl)-thiazol-2-yl]-hydrazide 
• 106578-09-0 6-Chloro-3-(2-phenyl-thiazol-4-yl)-chromen-2-one 
• 1260653-60-8 C₂₅H₁₆ClFN₄O₂ 
• 326913-97-7 6-chloro-3-[1-(phenylhydrazono)-ethyl]-chromen-2-one 
• 86100-06-3 8-chloro-3-methyl-1-phenyl-1H-chromeno[4,3-c]pyrazol-4-one 
• 1355025-94-3 6-chloro-3-(2-(3-hydroxycarbonyl)phenylamino)acetyl-2H-chromen-2-one 
• 1355026-02-6 6-chloro-3-[2,3-(dihydro-3-(3-hydroxycarbonylphenyl)-2-thioxo-1H-imidazol-5-yl)]-2H-chromen-2-one 
• 38486-12-3 5-chloro-salicylaldehyde azine 
• 1375188-11-6 3-(6-chloro-2-oxo-2H-chromen-3-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde 
• 1375188-25-2 5-((3-(6-chloro-2-oxo-2H-chromene-3-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1375188-18-3 5-((3-(6-chloro-2-oxo-2H-chromene-3-yl)-1-phenyl-1H-pyrazol-4-yl)methylene)dihydrothioxopyrimidine-4,6(1H,5H)-dione 
• 1430228-85-5 2-(3-(4-chlorophenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(6-chlorocoumarin-3-yl)thiazole 
• 1430228-89-9 2-(3-(4-bromophenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydropyrazol-1-yl)-4-(6-chlorocoumarin-3-yl)thiazole 

Relevant academic research and scientific papers

Microwave-assisted efficient and convenient one-pot synthesis of novel 3-(4-aminothieno[2,3-d]pyrimidin-5-yl)coumarins under solvent-free conditions

[Figure not available: see fulltext.] An efficient green synthesis of novel 3-(4-aminothieno[2,3-d]pyrimidin-5-yl)coumarins has been developed. One-pot reaction of 3-acetylcoumarin, malononitrile, and elemental sulfur, catalyzed by L-proline, resulted in the formation of thiophene derivatives, which were used as precursors for the synthesis of 3-(4-aminothieno[2,3-d]pyrimidin-5-yl)coumarins. Target compounds were prepared by a one-pot method or stepwise, and NH4OAc was exploited as a reagent and molten salt. Microwave irradiation method was successfully applied to afford the products in excellent yields.

Synthesis and characterisation of novel 3-(4-benzoyl-5-phenylfuran-2-yl) coumarins

Novel 3-(4-benzoyl-5-phenylfuran-2-yl)coumarin derivates were synthesised via a simple three-step reaction from salicylic aldehydes, ethyl 3-oxobutanoate and 1,3-diphenylpropane-1,3-dione. The synthesised compounds were characterised by NMR, MS and elemental analyses and single-crystal X-ray diffraction analysis.

A facile one pot multi component synthesis of alkyl 4-oxo-coumarinyl ethylidene hydrazono-thiazolidin-5-ylidene acetates and their antiviral activity

An efficient one-pot synthesis of alkyl 4-oxo-coumarinyl ethylidene hydrazono-thiazolidin-5-ylidene acetate derivatives has successfully been achieved via a three component cyclization reaction of various substituted 3-acetyl coumarins, thiosemicarbazide and dialkyl acetylenedicarboxylates, in presence of acetic acid. The isolated products were obtained in pure form with high yields through simple workup. The newly synthesised compounds structure was established on the basis of spectral (IR, 1H NMR, 13C NMR, ESI- mass) elemental analysis and single crystal X-ray data. All synthesised compounds were screened for their antiviral activity against a broad spectrum of human viruses in different cell cultures. Of the novel synthesised compounds, thirteen compounds exerted activity against Punta Toro virus, including compound IV-19, for which an antiviral potency was noted against a broad panel of DNA and RNA viruses as well.

Novel thiazoline-coumarin hybrid compounds containing sugar moieties: synthesis, biological evaluation and molecular docking study as antiproliferative agents

A new series of 2,3-thiazoline-coumarin hybrid compounds that containedd-glucose andd-galactose moieties (4a-g) were synthesized and their cytotoxic activity was evaluated against breast adenocarcinoma (MCF-7), human liver cancer (HepG2), human cervical cancer (HeLa), human melanoma cancer (SK-Mel-2), and human lung cancer (LU-1) cells. To reveal their selectivity toward cancer cells, the compounds were also tested against the human fibroblast cell line MRC-5. The synthesized compounds exhibited potent cytotoxic activity against the tested cell lines with IC50values of 1.18-11.32, 1.91-9.81, 1.96-13.16, 1.35-16.12, and 2.12-15.92 μM (against MCF-7, HepG2, HeLa, SK-Mel-2, and LU-1 cells, respectively) compared with Sorafenib, doxorubicin, and 5-fluorouracil. Interestingly, compounds4a-gdisplayed selectivity toward cancer cell lines over MRC-5 (IC503.97-25.75 μM). The most active compounds, including4d,4e, and4f, also displayed potent inhibitory activity against EGFR and HER2 kinases (IC500.15-0.31 and 0.15-0.25 μM, respectively) compared with the standard drug Sorafenib (IC50= 0.11 and 0.13 μM, respectively). Molecular docking also showed that the hydrogen binding interactions often occurred between the CO lactone of the coumarin ring and appropriate amino acid residues, which played a key role in enhancing its potency against both enzymes.

Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives

Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.

Synthesis and antiproliferative activity of hybrid thiosemicarbazone derivatives bearing coumarin and d-galactose moieties with EGFR inhibitory activity and molecular docking study

A series of substituted N-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)thiosemicarbazones 5a–5j of substituted 3-acetylcoumarins were synthesized with yields of 45–68%. All synthesized thiosemicarbazones were evaluated for cytotoxic activity against several cancer cell lines, such as human breast adenocarcinoma cells MCF7, human liver cancer cells HepG2, human cervical cancer cells HeLa, human melanoma cancer cells SK-Mel-2, and human lung cancer cells LU-1 by using the standard MTT assay. The IC50 values for these cancer cell lines were 1.28–11.81 μM (for MCF-7), 1.53–22.12 μM (for HepG2), 1.43–48.16 μM (for HeLa), 1.82–14.62 μM (for SK-Mel-2), and 1.74–14.62 μM (for LU-1). Most of the compounds were noncytotoxic against human WI-38 normal cell line (IC50 > 16.9 μM). The antiproliferative mechanisms were studied via EGFR inhibition and molecular docking. Docking studies revealed that there are strong interactions between a typical compound with the receptor of the EGFR tyrosine kinase domain with Erlotinib. [Figure not available: see fulltext.]

Synthesis and biological screening of thiosemicarbazones of substituted 3-acetylcoumarins having D-glucose moiety

Thiosemicarbazones 5a-j were synthesized with yields of 45–68% by condensation of 3-acetylcoumarins 3a-j and tetra-O-acetyl-β-D-thiosemicarbazide 4. All obtained thiosemicarbazones were screened for anti-microorganic activities against bacteria (B. subtilis, S. aureus, S. epidermidis, E. coli, P. aeruginosa, K. pneumoniae, S. typhimurium) and fungi (A. niger, C. albicans, S. cerevisiae, and A. flavus). Some compounds had significant inhibitory activity with MICs of 0.78–3.125 μM in comparison with 5a, including 5e,h,i for S. aureus, and 5c,f,i for S. epidermidis (Gram-(+) bacteria), 5c,f,g for E.coli, 5f for K. pneumoniae, 5b,c,g for P. aeruginosa, and 5i for S. typhimurium (Gram-(?) bacteria), 5d,h,i for A. niger, 5i for A. flavus, 5b,d,e,h for C. albicans, and 5i for S. cerevisiae. Compounds exhibited excellent activity against tested microorganism with MIC = 0.78 μM, including 5h,i (against S. aureus), 5h (against C. albicans), and 5i (against S. cerevisiae).

Ros inhibitory activity and cytotoxicity evaluation of benzoyl, acetyl, alkyl ester, and sulfonate ester substituted coumarin derivatives

Background: A number of non-steroidal anti-inflammatory drugs (NSAIDs) including aspirin, indomethacin, ibuprofen, flufenamic acid, and phenylbutazone are being clinically used to treat inflammatory disorders. These NSAIDs are associated with serious side

Synthesis and antiproliferative evaluation of novel biheterocycles based on coumarin and 2-aminoselenophene-3-carbonitrile unit

A series of novel coumarins with 2-amino-3-cyanoselenophen-5-yl unit on C-3 have been synthesized. These compounds prepared easily at room temperature, in a short time and in high yield. The importance of biheterocyclic units as dominant structural motif of coumarin derivatives has been well recognized. Anti-cancer activity screening on MCF-7 cell line allowed identification of 2-amino-5-(6-bromo-2-oxo-2H-chromen-3-yl)selenophene-3-carbonitrile with the highest level of cytotoxic activity with mean IC50 and cLogP (partition co-efficient) values 10.84 μM and 3.18, respectively. The most radical scavenging compound was also recognized. Graphic abstract: [Figure not available: see fulltext.].

Pyrazole–coumarin and pyrazole–quinoline chalcones as potential antitubercular agents

Pyrazole, coumarin, and quinoline are medicinally important moieties. In this study, two series of novel pyrazole–coumarin chalcones and pyrazole–quinoline chalcones were synthesized using multiple-step reactions. All the synthesized compounds were well c