42059-80-3

Basic information

• Product Name: 3-FORMYL-6-NITROCHROMONE
• Synonyms: 6-NITROCHROMONE-3-CARBALDEHYDE;6-NITRO-4-OXO-4H-1-BENZOPYRAN-3-CARBOXALDEHYDE;6-NITRO-4-OXO-4H-CHROMENE-3-CARBALDEHYDE;3-FORMYL-6-NITROCHROMONE;3-Formy-6-nitrochromone;6-nitro-4-oxochromene-3-carbaldehyde
• CAS NO: 42059-80-3
• Molecular Formula: C₁₀H₅NO₅
• Molecular Weight: 219.15
• Product Categories: Aldehydes;Benzopyrans;Bioactive Small Molecules;Building Blocks;C10-C12;Carbonyl Compounds;Cell Biology;Chemical Synthesis;F;Heterocyclic Building Blocks;Organic Building Blocks
• Mol File: 42059-80-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 157-161 °C(lit.)
• Boiling Point: 406.2 °C at 760 mmHg
• Flash Point: 207.6 °C
• Appearance: /
• Density: 1.641 g/cm³
• Vapor Pressure: 8.26E-07mmHg at 25°C
• Refractive Index: 1.723
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3-FORMYL-6-NITROCHROMONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-FORMYL-6-NITROCHROMONE(42059-80-3)
• EPA Substance Registry System: 3-FORMYL-6-NITROCHROMONE(42059-80-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 42059-80-3(Hazardous Substances Data)

Usage

Description

3-Formyl-6-nitrochromone, also known as 6-Nitro-4-oxo-4H-1-benzopyran-3-carboxaldehyde, is a benzopyran derivative characterized by its bicyclic heterocyclic structure, consisting of a benzene ring fused to a heterocyclic pyran ring. This molecule has demonstrated inhibitory activity against urease, making it a compound of interest in various research and industrial applications.

Uses

Used in Pharmaceutical Research:
3-Formyl-6-nitrochromone is used as a suitable reagent for studying the reversal of multidrug resistance in human colon cancer and mouse lymphoma cells transfected with the human MDR1 gene. Its application in this field aids in the investigation of potential treatments for overcoming drug resistance in cancer therapies.
Used in Chemical Synthesis:
3-FORMYL-6-NITROCHROMONE is also utilized as a reagent in the synthesis of uridine-based libraries, which are essential for the development of new drugs and the study of biological processes involving uridine and its derivatives.
Used in Enzyme Inhibition Studies:
Due to its inhibitory activity against urease, 3-Formyl-6-nitrochromone is employed in research aimed at understanding and developing methods to control the activity of this enzyme, which is relevant in various medical and industrial contexts.

InChI:InChI=1/C10H5NO5/c12-4-6-5-16-9-2-1-7(11(14)15)3-8(9)10(6)13/h1-5H

Upstream product

• 830-03-5 4-nitrophenol acetate 
• 100-02-7 4-nitro-phenol 
• 1450-76-6 1-(2-hydroxy-5-nitrophenyl)ethanone 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1162661-43-9 ethyl 3-acetyl-5-(5-nitro-2-hydroxybenzoyl)-2-hydroxybenzoate 
• 1162661-53-1 ethyl 3-(2-hydroxy-5-(2-hydroxy-5-nitrobenzoyl)phenyl)-3-oxopropanoate 
• 1135232-70-0 9-nitro-3-(4-chlorophenylsulfanyl)-2-oxo-2H,5H-pyrano[3,2-c]chromen-5-yl acetate 
• 1379795-54-6 C₃₀H₂₃N₅O₆ 
• 68287-73-0 (2-hydroxy-5-nitro-phenyl)-(1-phenyl-1H-pyrazol-4-yl)-methanone 

Relevant articles and documents

Polysubstituted heterocyclic derivative, preparation method thereof and application of polysubstituted heterocyclic derivative in medicine

The invention provides a polysubstituted heterocyclic derivative, a preparation method thereof and application of the polysubstituted heterocyclic derivative in medicine, and belongs to the technical field of medicinal chemistry. The polysubstituted heterocyclic derivative is a compound shown in a general formula I or II, a pharmaceutically acceptable salt or a solvate of the compound, and the compound can inhibit mRNA demethylase on the protease level and is used for treating diseases related to mRNA demethylase functions.

Design, synthesis and docking studies of novel thienopyrimidine derivatives bearing chromone moiety as mTOR/PI3Kα inhibitors

Two series of thienopyrimidine derivatives (10a-k, 16a-j) bearing chromone moiety were designed and synthesized. All the compounds were evaluated for inhibitory activity against mTOR kinase at a concentration of 10uM. Four selected compounds were further evaluated for the IC50 values against mTOR kinase, PI3Kα kinase and two cancer cell lines. Some of the target compounds exhibited moderate to excellent mTOR/PI3Kα kinase inhibitory activity and cytotoxicity. The most promising compound 16i showed good inhibitory activity against mTOR/PI3Kα kinase and good antitumor potency for H460 and PC-3 cell lines with IC50 values of 0.16 ± 0.03 μM, 2.35 ± 0.19 μM, 1.20 ± 0.23 μM and 0.85 ± 0.04 μM, which were 8.6, >5, 7.9 and 19.1 times more active than compound I (1.37 ± 0.07 μM, >10 μM, 9.52 ± 0.29 μM, 16.27 ± 0.54 μM), respectively. Structure-activity relationships (SARs) and docking studies indicated that the chromone moiety is necessary for the potent antitumor activity and cytotoxicity of these compounds. Substitution of the chromone moiety at the 6-position has a significant impact to the inhibitory activity, in particular a carboxylic acid group, produced the best potency.

One-pot synthesis of 3-formylchromones from bis-(trichloromethyl) carbonate/DMF

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