51070-05-4

Basic information

• Product Name: 1-phenylchromeno[4,3-c]pyrazol-4(1H)-one
• CAS NO: 51070-05-4
• Molecular Formula: C₁₆H₁₀N₂O₂
• Molecular Weight: 262.2628
• Mol File: 51070-05-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 464.2°C at 760 mmHg
• Flash Point: 234.5°C
• Density: 1.34g/cm³
• Vapor Pressure: 8.55E-09mmHg at 25°C
• Refractive Index: 1.697
• CAS DataBase Reference: 1-phenylchromeno[4,3-c]pyrazol-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenylchromeno[4,3-c]pyrazol-4(1H)-one(51070-05-4)
• EPA Substance Registry System: 1-phenylchromeno[4,3-c]pyrazol-4(1H)-one(51070-05-4)

Safety Data

• Hazardous Substances Data: 51070-05-4(Hazardous Substances Data)

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

• 136806-16-1 4-azido-2-oxo-2H-chromene-3-carbaldehyde 
• 100-63-0 phenylhydrazine 
• 52817-14-8 4-oxo-4H-chromene-3-carboxamide 
• 118-93-4 o-hydroxyacetophenone 
• 122-79-2 Phenyl acetate 
• 108-95-2 phenol 
• 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 
• 51751-34-9 4-hydroxycoumarin-3-carboxaldehyde 
• 39079-62-4 chromone-3-carboxylic acid 
• 51069-96-6 4-chloro-2-oxo-2H-chromene-3-carbaldehyde phenylhydrazone 

Relevant articles and documents

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, 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.

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.