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

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

Uses

Used in Pharmaceutical Industry:
4-Bromo-4-NitroChalcone is used as a pharmaceutical agent for its anti-inflammatory properties, helping to reduce inflammation and alleviate pain in various conditions.
Used in Anticancer Applications:
4-Bromo-4-NitroChalcone is used as an anticancer agent, exhibiting potential to inhibit the growth of cancer cells and contributing to the development of novel cancer treatments.
Used in Antimicrobial Applications:
4-Bromo-4-NitroChalcone is used as an antimicrobial agent, effective against a range of bacteria and other microorganisms, and can be utilized in the development of new antibiotics and antifungal agents.
Used in Organic Synthesis:
4-Bromo-4-NitroChalcone is used as an intermediate in organic synthesis, allowing for the creation of various other compounds with diverse applications in different industries.
Used in Medicinal Chemistry:
4-Bromo-4-NitroChalcone is used as a key component in medicinal chemistry research, aiding in the discovery and development of new drugs and therapies with improved efficacy and safety profiles.

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

• 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 
• 948840-96-8 (E)-1-(4-aminophenyl)-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.

Catalyst- and acid-free Markovnikov hydration of alkynes in a sustainable H2O/ethyl lactate system

An efficient and sustainable protocol for the hydration of alkynes has been developed under metal/acid/catalyst/ligand-free conditions in a water/ethyl lactate mixture. The hydrogen-bond network in the ethyl lactate and water mixture plays a crucial and decisive role in activating the alkynes for hydration to afford the corresponding methyl ketones. This strategy gives the Markovnikov (ketone) addition product selectively over other possible products. The essential role of hydrogen bonding has been confirmed by experimental and theoretical techniques. A probable mechanism has been suggested by various control tests. The efficacy of the method has been further explored for the competent production of value-added α,β-unsaturated carbonyl compounds through the reaction of aldehydes with alkynes as ketonic surrogates. The environmentally benign hydration method takes place under mild conditions, has broad functional-group compatibility, and uses the ethyl lactate/water (1:3) medium as a “green alternative” in the absence of any hazardous, harmful, or expensive substances.

Rapid abnormal [3+2]-cycloaddition of isatinN,N′-cyclic azomethine imine 1,3-dipoles with chalcones

The rapid synthesis of novel dicyclic spiropyrrolidine was reported, using [3+2]-cycloaddition of isatinN,N′-cyclic azomethine imine 1,3-dipoles, generated from the condensation of substituted isatins and pyrazolidones, with chalcones in 2-5 min. The dicy

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.

Synthesis, antitubercular activity, and QSAR analysis of substituted nitroaryl analogs: Chalcone, pyrazole, isoxazole, and pyrimidines

In the present investigation, 4-nitroacetophenone, on condensation with appropriate aldehydes in ethanolic sodium hydroxide solution, yielded the corresponding chalcones. These corresponding chalcones were reacted with hydrazine hydrate, urea, thiourea, a

Synthesis, characterization and fluorescence studies of 3,5-diaryl substituted 2-pyrazolines

A series of 2-pyrazolines have been synthesized from α, β unsaturated ketones and hydrazine hydrate with acetic/formic acid in ethanol/DMSO. The structures of 2-pyrazolines have been established by spectroscopic techniques i.e. UV, IR, 1H NMR, 13C NMR and micro element analysis. Fluorescence spectra were recorded in the solution at fixed concentration and same excitation wavelength at 290 nm. The absorption band positions of all the compounds broadly lie between 280 and 336 nm and fluorescence band positions in the range between 300 and 370 nm, the near ultraviolet region.

COMPOSITION FOR DIAGNOSING AMYLOID-RELATED DISEASE

There is provided a composition comprising a compound represented by general formula (I), wherein R1 represents a 5-iodothiophen-2-yl group or the like, and R2 represents a 4-dimethylaminophenyl group or the like. This composition is useful for diagnosis of an amyloid-related disease such as Alzheimer's disease because the compound has high binding specificity to amyloid β protein, high permeability through the blood-brain barrier, and a property of being rapidly eliminated from sites other than senile plaques in the brain.

Spectral properties and photochemical activity of chalcone derivatives

A relationship is found between spectral-luminescent and photochemical properties for mono-and disubstituted chalcone derivatives R1CO-CH=CHR2 [R1, R2 = Ph, 4-FC6H4, 4-BrC6H4, 2-furyl, 2-thienyl, 4-(PhCONH)C6H4, 4-NH2C6H4, 4-Me2NC6H4].

REACTION OF SCHIFF BASES OBTAINED FROM 4-AMINOANTIPYRINE AND 4-AMINO-1,2,4-TRIAZOLE WITH KETONES

With acetophenone and p-nitroacetophenone in alcohol and benzene media in the presence of acid N-arylidene-4-aminoantipyrines form α,β-unsaturated ketones, and with antipyrine the form aryldiantipyrylmethanes.With the same ketones N-arylidene-4-amino-1,2,4-triazoles form the products from addition at the azomethine bond.In both cases reaction with benzylideneacetone was not detected.