51070-05-4

Usage

Chemical structure

A complex structure that includes a phenyl group and a chromeno-pyrazole core.

Type of compound

A heterocyclic compound.

Biological and pharmacological activities

Has potential antioxidant, anti-inflammatory, and anticancer properties.

Medical applications

Being investigated for its potential role in the treatment of neurodegenerative diseases and as a potential drug candidate for various medical conditions.

Further research

Needed to fully understand the potential uses and effects of 1-phenylchromeno[4,3-c]pyrazol-4(1H)-one in medicinal and biological applications.

Upstream product

• 39079-62-4 chromone-3-carboxylic acid 
• 100-63-0 phenylhydrazine 
• 51751-34-9 4-hydroxycoumarin-3-carboxaldehyde 
• 52817-14-8 4-oxo-4H-chromene-3-carboxamide 
• 1448308-08-4 (E)-4-chloro-3-((2-phenylhydrazono)methyl)-2H-chromen-2-one 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 50743-17-4 4-oxo-4H-1-benzopyran-3-carbonitrile 
• 50329-91-4 4-chloro-3-formylcoumarin 
• 59-88-1 phenylhydrazine hydrochloride 
• 136806-16-1 4-azido-2-oxo-2H-chromene-3-carbaldehyde 
• 51069-96-6 4-chloro-2-oxo-2H-chromene-3-carbaldehyde phenylhydrazone 
• 118-93-4 o-hydroxyacetophenone 
• 122-79-2 Phenyl acetate 
• 108-95-2 phenol 

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.

Ring transformation of chromone-3-carboxamide under nucleophilic conditions

The chemical reactivity of chromone-3-carboxamide was studied towards a series of nitrogen and carbon nucleophiles. Treatment of carboxamide with some primary amines gave chromane-2,4-diones. Condensation of carboxamide with hydrazine hydrate, phenyl hydrazine and hydroxylamine hydrochloride afforded chromenopyrazoles and chromenoisoxazole, respectively. Reaction of carboxamide with guanidine hydrochloride, cyanoguanidine and thiourea resulted in ring transformation producing chromenopyridines. The chemical behavior of carboxamide was also studied towards ethylenediamine, o-phenylenediamine, 2-aminophenol and 2-aminothiophenol. A variety of products were isolated from the reaction of carboxamide with some carbon nucleophiles.

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 new substituted chromen[4,3-c]pyrazol-4-ones and their antioxidant activities

A series of new coumarin derivatives 4 containing a 4-arylbut-3-en-2-one moiety were synthesized by condensation of 3-acetylcoumarin 1 with aryl aldehydes 2 in chloroform in the presence of piperidine. The interactions of 3-formyl-4-chlorocoumarin (3) with nitrogen-containg nucleophiles leading to the corresponding substituted chromen-[4,3- c]pyrazol-4-ones 5 are described. The structures of the obtained compounds were established on the basis of 1D NMR, 2D NMR and IR and further the compounds were evaluated for possible antioxidant activities. The coumarinic chalcone 4a has been found to be the most active (IC50 = 2.07 μM) in this study.

A rapid access to new coumarinyl chalcone and substituted chromeno[4,3-c]pyrazol-4(1H)-ones and their antibacterial and DPPH radical scavenging activities

A series of new coumarin derivatives 4 containing a chalcone moiety were synthesized by condensation of 3-acetyl-4-hydroxycoumarin 1 with aryl or heteroaryl aldehydes 2 in the presence of piperidine in chloroform. The interaction of 3-formyl-4-chloro-coumarin 3 with nitrogen compound nucleophiles are described and lead to the corresponding substituted chromen[4,3-c] pyrazol-4-ones 5. The structures of the obtained compounds were established on the basis of IR|1D|2D NMR, while crystal structure of 3-acetyl-4-hydroxy coumarin 1 was determined using X-ray diffraction and further were evaluated for possible antibacterial and antioxidant activities. The coumarinic chalcone 4d has been found to be the most active (IC50 = 2.07 μM) in this study.

On the reaction of 3-cyanochromones with phenyl- and methylhydrazines: Structural revision and a simple synthesis of chromeno[4,3-c]pyrazol-4-ones

(Chemical Equation Presented) Reactions of 3-cyanochromones with phenylhydrazine gave the corresponding 5-amino-4-salicyloyl-1-phenylpyrazoles, 2-aminochromone-3-carbaldehyde N-phenylhydrazones, and 1-phenylchromeno[4,3-c] pyrazol-4(1H)-one, depending on

Reactions of 4-chloro-3-formylcoumarin with arylhydrazines

The interaction of 3-formyl-4-coumarin with arylhydrazine hydrochlorides in the presence of sodium acetate gave the corresponding 3-arylhydrazonomethyl-4- chlorocoumarin, and with phenylhydrazine, 4-bromo- and 4-chlorophenylhydrazine hydrochlorides in the

Synthesis of some of the antibacterial compounds from 4-hydroxycoumarins: Part II

4-Hydroxy-2H-2-oxo-3-methylidene-urea[1]benzopyrans 2a-d, 4-hydroxy-2H-2-oxo-3-methylidene-thiourea[1]benzopyrans 2e-h, 4-hydroxy-2H-2-oxo-3-methylidene-guanidine[1]benzopyrans 2i-I are obtained from 1a-d on treatment with urea, thiourea, and guanidine re

Heterocyclic -Condensed Coumarins from 4-Azido-3-coumarincarbaldehydes

4-Azido-3-coumarincarbaldehydes 2a-d are useful starting materials for syntheses of a variety of 3,4-disubstituted coumarins as well as heterocyclic -fused coumarins, e. g. isoxazoles, pyrazoles and 1,5-diazepines, under mild conditions.In these reacti