2764-19-4

Upstream product

• 51751-37-2 2-Methyl-4-oxo-4H-<1>benzopyran-3-carboxylic acid 
• 59-88-1 phenylhydrazine hydrochloride 
• 114954-02-8 1-phenyl-3-methyl-4-cyano-5-(2-hydroxyphenyl)pyrazole 
• 2587-10-2 4-hydroxy-3-(N-(2-phenylamino)ethanimidoyl)-2H-chromen-2-one 
• 100-63-0 phenylhydrazine 
• 2555-37-5 3-acetyl-4-hydroxychromen-2-one 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 67140-88-9 2-Methyl-4-oxo-4H-<1>benzopyran-3-carbonitrile 
• 41461-99-8 3-methyl-1,5-diphenyl-1H-pyrazole-4-carbaldehyde 
• 90-02-8 salicylaldehyde 
• 103593-74-4 3-{1-[(E)-2-phenylhydrazono]ethyl}-2H-chromen-2-one 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 3949-36-8 3-acetylcoumarin 

Relevant academic research and scientific papers

Structural investigations on coumarins leading to chromeno[4,3-c]pyrazol-4-ones and pyrano[4,3-c]pyrazol-4-ones: New scaffolds for the design of the tumor-associated carbonic anhydrase isoforms IX and XII

Human carbonic anhydrases (hCAs, EC 4.2.1.1) IX and XII are overexpressed in a wide variety of cancers and are considered available drug targets for anti-tumor therapy since their inhibition has been shown to reduce tumor growth and metastasis. A set of coumarin derivatives (1–10) and several 1-aryl and 2-aryl-substituted chromeno[4,3-c]pyrazol-4-ones (11–37) and pyrano[4,3-c]pyrazol-4-ones (38–39) were synthesized and tested against the tumor-associated hCAs IX and XII and the cytosolic isoforms hCAs I and II. Several compounds were potent (Ki i = 5.6–9.6 nM), while none were effective against the off-target cytosolic hCAs I and II. Some selected inhibitors (6, 11, 13, 19, 21, 25, 31 and 39) showed activity as antiproliferative agents on HT-29 colon cancer cell lines both in normoxic and hypoxic conditions. This finding led us to hypothesize for these derivatives more than one mechanism of action, involving hCAs IX and XII inhibition in hypoxia and other not identified target(s) in normoxia.

Synthesis of dibenzopyranones and pyrazolobenzopyranones through copper(0)/Selectfluor system-catalyzed double C[sbnd]H activation/oxygen insertion of 2-arylbenzaldehydes and 5-arylpyrazole-4-carbaldehydes

A mild and efficient protocol for the synthesis of dibenzopyranones and pyrazolobenzopyranones was developed involving a copper(0)/Selectfluor system-catalyzed double C[sbnd]H activation/oxygen insertion of 2-arylbenzaldehydes and 5-arylpyrazole-4-carbaldehydes. Preliminary mechanistic studies suggest that both water and dioxygen act as the oxygen source in the formation of pyranone scaffolds.

Copper-catalyzed cyclization of 3-acylcoumarin hydrazone using air as the oxidant: Efficient synthesis of pyrazole-fused coumarin derivatives

An efficient, convenient Cu-catalyzed formation of chromeno[4,3-c]pyrazol-4(1H)-ones is reported. In this atom economic process, readily available 3-acylcoumarin hydrazone is oxidative cyclized by direct C-N bond formation. Air has been successfully used

Potassium carbonate-mediated efficient and convenient synthesis of 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1 H)-ones

Unprecedented cyclization was observed during N-sulfonylation of 3-[1-(phenylhydrazono)-ethyl]-chromen-2-one in pyridine, affording 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones. To avoid use of noxious pyridine, reaction was tried in different basic

Synthesis, biological evaluation and docking analysis of 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones as potential cyclooxygenase-2 (COX-2) inhibitors

As a part of our continued efforts to discover new COX inhibitors, a series of 3-methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones were synthesized and evaluated for in vitro COX inhibitory potential. Within this series, seven compounds (3a-d, 3h, 3k and 3

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.

Study on the cyclization methods of 3-[1-(phenyl-hydrazono)ethyl]-chromen- 2-ones

Some new methods, such as air oxidation, catalytic oxidation, and solvent-free synthesis, are developed for the synthesis of 3-methyl-1- phenylchromeno[4,3-c]pyrazol-4(1H)-ones(2) from the cyclization of 3-[1-(phenyl-hydrazono)ethyl]-chromen-2-ones(1). Co

Microwave-assisted synthesis of 3-methyl-1-phenyl-chromeno[4,3-c]pyrazol- 4(1H)-ones under solvent-free conditions

A novel microwave-assisted method for the synthesis of 3-methyl-1- phenylchromeno[4,3-c]pyrazol-4(1H)-ones by the cyclization of 3-[1-(phenylhydrazono)ethyl]chromen-2-ones with CuO/SBA-15 under solvent-free conditions is described. The reaction gave the c

X-ray supramolecular structure, NMR spectroscopy and synthesis of 3-methyl-1-phenyl-1H-chromeno[4,3-c]pyrazol-4-ones formed by the unexpected cyclization of 3-[1-(phenylhydrazono)ethyl]-chromen-2-ones

The molecular structures of nine 3-methyl-1-phenyl-1H-chromeno[4,3-c] pyrazol-4-one isomers, obtained by the oxidative cyclization of the corresponding 1-phenylhydrazono chromen-2-ones with copper acetate as catalyst, are reported. The molecular and supra

Ring closure reactions of 3-arylhydrazonoalkyl-quinolin-2-ones to 1-aryl-pyrazolo[4,3-c]quinolin-2-ones

4-Hydroxy-3-arylhydrazonoalkyl-2-quinolones 6 or reactive derivatives such as 3-arylhydrazonoalkyl-4-tosyloxy-2-quinolones 7 or 4-chloro-3- arylhydrazonoalkyl-2-quinolones 14, which are obtained via 3-acyl-4- hydroxyquinolones 4, 10 or 3-phenylaminomethylene-quinoline-2,4-diones 12, cyclize in excellent yields to 1-aryl-pyrazolo[4,3-c]quinolin-4-ones (11). The cyclization conditions were investigated by differential scanning calorimetry (DSC).