13909-51-8

Basic information

• Product Name: 4Bromo-4-NitroChalcone
• Synonyms: 4Bromo-4-NitroChalcone
• CAS NO: 13909-51-8
• Molecular Formula: C₁₅H₁₀BrNO₃
• Molecular Weight: 332.1488
• Mol File: 13909-51-8.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4Bromo-4-NitroChalcone(CAS DataBase Reference)
• NIST Chemistry Reference: 4Bromo-4-NitroChalcone(13909-51-8)
• EPA Substance Registry System: 4Bromo-4-NitroChalcone(13909-51-8)

Safety Data

• Hazardous Substances Data: 13909-51-8(Hazardous Substances Data)

Usage

General Description

4-Bromo-4-NitroChalcone is a chemical compound with the molecular formula C15H9BrO3N. It is a bright yellow solid that is soluble in organic solvents. 4Bromo-4-NitroChalcone is a chalcone, which is a type of flavonoid compound commonly found in plants. It is often used in organic synthesis and medicinal chemistry due to its potent biological activities, including anti-inflammatory, anti-cancer, and anti-microbial properties. 4-Bromo-4-NitroChalcone is also being investigated for its potential applications in pharmaceuticals and other industrial purposes.

Upstream product

• 937-31-5 (4-Nitrophenyl)acetylene 
• 1122-91-4 4-bromo-benzaldehyde 
• 100-19-6 (4-nitrophenyl)ethanone 
• 61098-05-3 4-{[1-(4-Bromo-phenyl)-meth-(E)-ylidene]-amino}-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one 
• 27895-60-9 2-(4-bromo-benzylidenamino)-ethanol 

Downstream Products

• 26128-65-4 4-bromo-4'-aminochalcone 
• 1416989-26-8 5-(4-bromophenyl)-3-(4-nitrophenyl)-4,5-dihydro-1H-pyrazole 
• 1416989-44-0 6-(4-bromophenyl)-4-(4-nitrophenyl)-5,6-dihydropyrimidin-2(1H)-thione 
• 1416989-35-9 6-(4-bromophenyl)-4-(4-nitrophenyl)-5,6-dihydropyrimidin-2(1H)-one 
• 25870-89-7 1-(4-isothiocyanatophenyl)-3-(4-bromophenyl)-2-propen-1-one 

Relevant articles and documents

Emulating Natural Product Conformation by Cooperative, Non-Covalent Fluorine Interactions

Pervasive in Nature, the propane unit is an essential component of numerous bioactive molecules. These range from acyclic systems, such as the neurotransmitter γ-aminobutyric acid, through to the bicyclic nuclei of various chromanes and dihydrobenzofurans. In the latter case, cyclisation via cyclic ether formation ensures a highly pre-organised structure, whilst linear scaffolds display more dynamic conformational behaviour resulting from rotation about the two internal C(sp3)–C(sp3) bonds. In this study, the replacement of -[CH2]- units by -[CHF]- centres is evaluated as a strategy to achieve acyclic conformational control by hindering these internal rotations. Reinforcing, non-covalent fluorine interactions are validated as powerful design features that result in programmable conformational behaviours: These are encoded by the relative configuration of each centre. By exploiting cooperative neighbouring stereoelectronic effects in a multi-vicinal fluoroalkane it is possible to emulate the overall conformation of the dihydrobenzofuran scaffold found in a variety of natural products with an acyclic mimic. This is described as a function of two bond vectors at the chain termini and validated by combined theoretical, crystallographic and spectroscopic analyses. In view of the favourable physicochemical properties associated with fluorine introduction, this approach to bioactive scaffold design may prove to be expansive.

ADME properties, bioactivity and molecular docking studies of 4-amino-chalcone derivatives: new analogues for the treatment of Alzheimer, glaucoma and epileptic diseases

In this study, in vitro inhibition effects of (E)-1-(4-aminophenyl)-3-(aryl) prop-2-en-1-one (4-amino-chalcones) derivatives (3a–o) on acetylcholinesterase (AChE) enzyme and human erythrocyte carbonic anhydrase I and II isoenzymes (hCA I- II) were investigated. And also, the biological activities of 4-amino-chalcone derivatives against enzymes which names are acetylcholinesterase (PDB ID: 1OCE), human Carbonic Anhydrase I (PDB ID: 2CAB), human carbonic anhydrase II (PDB ID: 3DC3), were compared. After the results obtained, ADME/T analysis was performed in order to use 4-amino-chalcone derivatives as a drug in the future. Effective inhibitors of carbonic anhydrase I and II isozymes (hCAI and II) and acetylcholinesterase (AChE) enzymes with Ki values in the range of 2.55 ± 0.35–11.75 ± 3.57?nM for hCA I, 4.31 ± 0.78–17.55 ± 5.86?nM for hCA II and 96.01 ± 25.34–1411.41 ± 32.88?nM for AChE, respectively, were the 4-amino-chalcone derivatives (3a–o) molecules.

Synthesis, Antiproliferative and Cytotoxic Activities, DNA Binding Features and Molecular Docking Study of Novel Enamine Derivatives

Novel enamine derivatives were synthesized from the reaction of lactone and chalcones and their antiproliferative and cytotoxic activities against six cancer cell lines (e. g., HeLa, HT29, A549, MCF7, PC3 and Hep3B) and one normal cell lines (e. g., FL) were investigated along with their mode of interactions with CT-DNA. Most of the enamine derivatives with IC50 values of 86–168 μM demonstrated much stronger antiproliferative activity than the starting molecules against the cancer cells. While, among the enamine derivatives, four compounds displayed higher cytotoxic potency than the control drugs (5-fluorouracil and cisplatin) against the Hep3B cell lines, these compounds did not exhibit any significant toxicity against normal cells, FL. The UV/VIS spectral data suggest that eight compounds cause hypochromism with a slight bathochromic shift (～6 nm), indicating that they bind to the DNA by way of an intercalative or minor groove binding mode. The binding constants of the compounds are in the range of 0.1×103 M?1–2.3×104 M?1. The antiproliferative activity of studied enamine derivatives could possibly be due to their DNA binding as well as their cytotoxic properties. In addition to these assays, the chalcones and enamine derivatives were investigated by molecular docking to calculate the synergistic effect of antiproliferative activities against six human cancer cell lines.