956-04-7

Usage

Uses

Used in Organic Synthesis:
4-Chlorochalcone serves as a valuable intermediate in the synthesis of various organic compounds. Its reactivity in conjugate addition reactions, particularly with pyrrole in the presence of AlKIT-5, makes it a useful building block for creating complex organic molecules and pharmaceuticals.
Used in Pharmaceutical Development:
Given its structural features and synthetic utility, 4-Chlorochalcone may be employed in the development of new pharmaceutical agents. Its ability to form derivatives through conjugate addition reactions could be harnessed to create novel compounds with potential therapeutic applications.
Used in Catalyst Research:
The use of 4-Chlorochalcone in reactions with catalysts like AlKIT-5 highlights its potential in the field of catalysis research. Studying its interactions with various catalysts can provide insights into improving reaction efficiency and developing new catalytic systems for organic synthesis.
Used in Material Science:
The crystalline nature of 4-Chlorochalcone, with its monoclinic system and specific space group, suggests potential applications in material science. Its structural properties could be leveraged in the design of new materials with unique characteristics for various industrial applications.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 4541, 1987 DOI: 10.1016/S0040-4039(00)96558-4

InChI:InChI=1/C15H11ClO/c16-14-9-6-12(7-10-14)8-11-15(17)13-4-2-1-3-5-13/h1-11H/b11-8+

Upstream product

• 13944-95-1 2-(phenacylsulfanyl)-1,3-benzothiazole 
• 104-88-1 4-chlorobenzaldehyde 
• 98-86-2 acetophenone 
• 61098-04-2 4-(4-chlorobenzylideneamino)-1,2-dihydro-1,5-dimethyl-2-phenylpyrazol-3-one 
• 38895-95-3 p-chlorochalcone dibromide 
• 905811-24-7 [[3-(4-chlorophenyl)-1-phenyl-2-propynyl]oxy]-trimethylsilane 
• 6969-01-3 trans-2,3-epoxy-3-(4-chlorophenyl)-1-phenylpropan-1-one 
• 141-97-9 ethyl acetoacetate 
• 242133-10-4 (Z,Z)-2,2'-thiobis(3-(4-chlorophenyl)-1-phenylprop-2-en-1-one) 
• 123-54-6 acetylacetone 
• 269725-81-7 3-(p-chlorophenyl)-3-hydroxy-1-phenylpropan-1-one 
• 24721-26-4 (2Z)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one 
• 70-11-1 α-bromoacetophenone 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 

Downstream Products

• 4471-03-8 (+/-)-erythro-3-(4-chloro-phenyl)-5-oxo-2,5-diphenyl-valeric acid 
• 61595-98-0 1-(4-bromo-phenyl)-5-(4-chloro-phenyl)-3-phenyl-4,5-dihydro-1H-pyrazole 
• 53440-95-2 4-(4-chloro-phenyl)-2-oxo-6-phenyl-4H-[1,3]oxazine-3-sulfonyl chloride 
• 38895-95-3 p-chlorochalcone dibromide 
• 68257-76-1 3-(4-chloro-phenyl)-4-(3-methyl-4-nitro-isoxazol-5-yl)-1-phenyl-butan-1-one 
• 55434-31-6 6-(4-chloro-phenyl)-2,4-diphenyl-6H-[1,3]thiazine 
• 76729-97-0 [4-(4-Chloro-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-phenyl-methanone 
• 89478-34-2 2-ethoxycarbonyl-4-p-chlorophenyl-6-phenylpyrylium trifluoromethanesulphonate 
• 74007-62-8 3-(4-Chloro-phenyl)-3-methoxy-2-phenyl-propionic acid methyl ester 
• 74007-56-0 2-(4-Chloro-phenyl)-3,3-dimethoxy-1-phenyl-propan-1-one 
• 150356-88-0 5-(4-chlorophenyl)-2,3-dihydro-7-phenyl-2-thioxopyrido<2,3-d>pyrimidin-4(1H)-one 
• 113854-25-4 4-(4-Chloro-phenyl)-3-methyl-1,6-diphenyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine 
• 90016-02-7 6-(4-chlorophenyl)-2-oxo-4-phenyl-3-cyclohexene-1-carboxylic acid ethyl ester 
• 344244-89-9 5-Benzoyl-4-(4-chloro-phenyl)-6-oxo-2-phenyl-cyclohex-1-enecarbonitrile 

Relevant academic research and scientific papers

Synthesis, crystal structure, anti-HIV, and antiproliferative activity of new pyrazolylthiazole derivatives

The development of new HIV-1 non-nucleoside reverse transcriptase inhibitors offers the possibility of generating novel structures of increased potency. Based on the bioisosteric principle, new series of N′-benzylidene-2-(5-(4-chlorophenyl)-3-phenyl-4,5-dihydropyrazol-1-yl)thiazole-4-carbohydrazide schiff bases 5a–x containing 1,3-thiazole clubbed with 2-pyrazoline was synthesized and characterized by spectroscopic techniques. The structure of the synthesized compounds was unambiguously confirmed by single-crystal X-ray diffraction analysis of compound 5k. All the new analogs were evaluated in vitro for antiviral activity against the replication of HIV-1 and HIV-2 in MT4 cells using MTT assay. The results showed that only compounds 5n, and 5r possess potent activity against HIV-1 replication (IC50 = 0.50, 0.45 μM, SI = 3 and 5), respectively. None of the compounds are active against HIV-2. Furthermore, compounds 5a, 5i, 5n, and 5r were evaluated for their antiproliferative activity against two solid tumor-derived cell lines consisting MCF-7 (breast cancer) and Hep-G2 (human hepatocarcinoma).

Synthesis, characterization and antichagasic evaluation of thiosemicarbazones prepared from chalcones and dibenzalacetones

Chagas disease is a neglected disease, being one of the leading causes of death from infectious diseases. In view of the severity of this pathology, this work describes the synthesis of new thiosemicarbazones derived from chalcones and dibenzalacetones as potential drugs for the treatment of this disease. The structures of all compounds were elucidated by infrared (IR) and nuclear magnetic resonance (1H and 13C NMR) spectroscopies. The chalcone derived thiosemicarbazones 10-14 were tested against the intracellular amastigote form of the protozoan Trypanosoma cruzi and had their cytotoxicity assessed using LLC-MK2 cells. The compound 10 (IC50 = 12.25 μM) presented the best activity when compared with the standard drug benznidazole (IC50 = 5.64 μM).

A new method for the synthesis of chalcone derivatives promoted by PPh3/I2under non-alkaline conditions

A straightforward and general method has been developed for the synthesis of chalcone derivatives by a Claisen-Schmidt reaction in the presence of PPh3/I2 in 1,4-dioxane under reflux temperatures. With the condensation of the aromatic ketone and aldehyde occurring at non-strongly alkaline conditions, our proposed method significantly expands the range of applicable substrates, especially for groups that are unstable under alkaline conditions.

Synthesis, characterization and biological evaluation of new 3,5-disubstituted-pyrazoline derivatives as potential anti-Mycobacterium tuberculosis H37Ra compounds

A total of fourteen pyrazoline derivatives were synthesized through cyclo-condensation reactions by chalcone derivatives with different types of semicarbazide. These compounds were characterized by IR, 1D-NMR (1H, 13C and Distortionless Enhancement by Polarization Transfer-DEPT-135) and 2D-NMR (COSY, HSQC and HMBC) as well as mass spectroscopy analysis (HRMS). The synthesized compounds were tested for their antituberculosis activity against Mycobacterium tuberculosis H37Ra in vitro. Based on this activity, compound 4a showed the most potent inhibitory activity, with a minimum inhibitory concentration (MIC) value of 17 μM. In addition, six other synthesized compounds, 5a and 5c–5g, exhibited moderate activity, with MIC ranges between 60 μM to 140 μM. Compound 4a showed good bactericidal activity with a minimum bactericidal concentration (MBC) value of 34 μM against Mycobacterium tuberculosis H37Ra. Molecular docking studies for compound 4a on alpha-sterol demethylase was done to understand and explore ligand– receptor interactions, and to hypothesize potential refinements for the compound.

Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide

The selective reduction of ?,￠-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ￠ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ￠-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.

Heteroleptic copper(I) complexes as energy transfer photocatalysts for the intermolecular [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides

The [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides can be effectively catalyzed by heteroleptic copper(I) complexes. The reactions were carried out under mild reaction conditions and the products were obtained in 20–72% yield under visible light irradiation. The copper-based photocatalyst comprised of the rigid phenanthroline ligand with substituents at the 2,9-positions and the 4,7-positions showed high activity in the photodimerization via an energy transfer pathway.

New promising levofloxacin derivatives: Design, synthesis, cytotoxic activity screening, Topo2β polymerase inhibition assay, cell cycle apoptosis profile analysis

Newly designed levofloxacin analogues were synthesized to act as topoisomerase II beta inhibitors (Topo2β). Their cytotoxic activity was screened against breast, liver, and leukemia cancer cell lines. The best activity against liver cancer cell line (Hep3B) was exhibited by the target compounds 3c, 3e, 4a, and 6d (IC50 = 2.33, 1.38, 0.60 and 0.43, respectively). (L-SR) leukemia cancer cell line was pronouncedly affected by compounds 3b, 3g and 4a (IC50 = 1.62, 1.41 and 1.61, sequentially). 3c possessed the best activity against breast cancer cell line (MCF-7) with IC50 = 0.66. Compounds 3c, 3e, 3g, 4a and 4c exhibited Topo2β inhibition activities exceeding etoposide and levofloxacin as reference drugs and variant cell lines. In DNA-Flow cytometry cell cycle analysis, compound 3c arrested the cell cycle at G2/M phase like etoposide and levofloxacin, while compounds 3e and 4a exhibit its arrest at S phase. In addition, 3c, 3e and 4a showed a significant elevation in active caspase-3 levels (10.01, 8.98 and 10.71 folds, respectively). The effect of the new compounds on normal cells was also investigated including breast (MCF10a), liver (THLE2), and lymphocytic (PCS-800-011) normal cell lines.

Modular access to 1,2-allenyl ketones based on a photoredox-catalysed radical-polar crossover process

Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developedviathe reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and allenation, the mechanism based on a photoredox-neutral-catalysed radical-polar crossover process has been proposed. Synthetic applications of allenes have also been demonstrated.

Synthesis of lithium/cesium-Zagronas from zagrosian natural asphalt and study of their activity as novel, green, heterogeneous and homogeneous nanocatalysts in the Claisen–Schmidt and Knoevenagel condensations

A novel, heterogeneous and homogeneous basic nanocatalysts were synthesized by grafting of lithium and cesium on zagrosian natural asphalt sulfonate (Li/Cs-Zagronas). The activity of these catalysts was examined in the Claisen–Schmidt and Knoevenagel condensations under mild reaction conditions. Li/Cs-Zagronas were characterized by FT-IR spectroscopy, scanning electron microscopy, X-ray diffraction, energy-dispersive spectroscopy, inductively coupled plasma and thermogravimetric analysis techniques. These nanocatalysts were removed by simple filtration and reused several times without any deterioration of activity.

Synthesis of chalcone derivatives by phthalhydrazide-functionalized tio2-coated nano-fe3o4 as a new heterogeneous catalyst

Phthalhydrazide immobilized on TiO2-coated nano Fe3O4 (Fe3O4-P) was synthesized and characterized by FT-IR, XRD, SEM, EDS and VSM analysis. The resulting magnetic nanocatalyst was used as a catalyst for the synthesis of chalcone derivatives which affords the desired products in good to excellent yields. This catalyst can be isolated readily after completion of the reaction by an external magnetite field and reused several times without significant loss of activity.