22966-15-0

Usage

InChI:InChI=1/C15H10Cl2O/c16-13-8-6-11(14(17)10-13)7-9-15(18)12-4-2-1-3-5-12/h1-10H/b9-7+

Upstream product

• 874-42-0 2,4-dichlorobenzaldeyhde 
• 98-86-2 acetophenone 
• 536-74-3 phenylacetylene 
• 1217899-20-1 3-(2,4-dichlorophenyl)-1-phenylprop-2-en-1-ol 
• 100-52-7 benzaldehyde 
• 2234-16-4 1-(2,4-dichlorophenyl)ethan-1-one 

Downstream Products

• 107916-37-0 2,3-dichloro-3-(2,4-dichloro-phenyl)-1-phenyl-propan-1-one 
• 68257-78-3 3-(2,4-dichloro-phenyl)-4-(3-methyl-4-nitro-isoxazol-5-yl)-1-phenyl-butan-1-one 
• 94360-57-3 cis-1-benzoyl-3,3-dicyano-2-(2,4-dichlorophenyl)cyclopropane 
• 127394-74-5 4-(2,4-Dichloro-phenyl)-2-ethoxy-6-phenyl-nicotinonitrile 
• 94360-04-0 2-[1-(2,4-Dichloro-phenyl)-3-oxo-3-phenyl-propyl]-malononitrile 
• 133961-86-1 3-[1-(2,4-Dichloro-phenyl)-3-oxo-3-phenyl-propylsulfanyl]-propionic acid 
• 1094463-27-0 3-(2,4-dichlorophenyl)-1-phenylpropan-1-one 
• 1262853-26-8 2-(2,4-dichlorophenyl)-4-oxo-4-phenylbutanenitrile 
• 1269059-59-7 (2R,3S)-tert-butyl 3-(2,4-dichlorophenyl)-2-(diphenylmethyleneamino)-5-oxo-5-phenylpentanoate 
• 1266096-14-3 (R)-tert-butyl 2-oxo-5-((S)-1-(2,4-dichlorophenyl)-3-oxo-3-phenylpropyl)-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 1322715-45-6 1-(2,4-dichlorophenyl)-3-oxo-3-phenylpropane-1-sulfonic acid 
• 1322715-68-3 methyl 1-(2,4-dichlorophenyl)-3-oxo-3-phenylpropane-1-sulfonate 
• 1247902-03-9 3-cyano-2-(1H-indol-3-yl)-4-(2,4-dichlorophenyl)-6-phenylpyridine 
• 402939-91-7 3-(2,4-dichlorophenyl)-1,5-diphenyl-2-pyrazoline 

Relevant academic research and scientific papers

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.

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.

Environmentally benign synthesis of substituted pyrazoles as potent antioxidant agents, characterization and docking studies

Oxidative stress is an important cause of neurogenerative diseases; treatment with a reliable antioxidant with no side effects is a potential tool?to overcome with such diseases. The aim of this study is to explore new and effective antioxidants and their

Rapid umpolung Michael addition of isatin N, N ′-cyclic azomethine imine 1,3-dipoles with chalcones

The umpolung Michael addition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones is reported. The reaction could be finished within a very short time (0.3-2 min), with 3,3-disubstituted oxindole derivatives obtained in moderate to excellent yields with promising dr values. Unusual Michael adducts were obtained in moderate to high yields (26-98%) with low to high diastereoselectivities (0.8: 1 to 8.5: 1 dr). All the synthesized compounds (3, 3′, 4, 5, 5′, 7, 7′, 9 and 9′) were well characterized by FTIR, NMR, and mass spectral analyses and further confirmed by the single-crystal X-ray diffraction analysis of compounds 3aa and 4n.

Antiproliferative effects of chalcones on T cell acute lymphoblastic leukemia-derived cells: Role of PKCβ

In this study, a series of 20 chalcone derivatives was synthesized, and their antiproliferative activity was tested against the human T cell acute lymphoblastic leukemia-derived cell line, CCRF-CEM. On the basis of the structural features of the most active compounds, a new library of chalcone derivatives, according to the structure–activity relationship design, was synthesized, and their antiproliferative activity was tested against the same cancer cell line. Furthermore, four of these derivatives (compounds 3, 4, 8, 28), based on lower IC50 values (between 6.1 and 8.9 μM), were selected for further investigation regarding the modulation of the protein expression of RACK1 (receptor for activated C kinase), protein kinase C (PKC)α and PKCβ, and their action on the cell cycle level. The cell cycle analysis indicated a block in the G0/G1 phase for all four compounds, with a statistically significant decrease in the percentage of cells in the S phase, with no indication of apoptosis (sub-G0/G1 phase). Compounds 4 and 8 showed a statistically significant reduction in the expression of PKCα and an increase in PKCβ, which together with the demonstration of an antiproliferative role of PKCβ, as assessed by treating cells with a selective PKCβ activator, indicated that the observed antiproliferative effect is likely to be mediated through PKCβ induction.

Aryl-4,5-dihydro-1H-pyrazole-1-carboxamide derivatives bearing a sulfonamide moiety show single-digit nanomolar-to-subnanomolar inhibition constants against the tumor-associated human carbonic anhydrases IX and XII

A series of new 3-phenyl-5-aryl-N-(4-sulfamoylphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide derivatives was designed here, synthesized, and studied for carbonic anhydrase (CAs, EC 4.2.1.1) inhibitory activity against the human (h) isozymes I, II, and VII (cytosolic, off-target isoforms), and IX and XII (anticancer drug targets). Generally, CA I was not effectively inhibited, whereas effective inhibitors were identified against both CAs II (KIs in the range of 5.2-233 nM) and VII (KIs in the range of 2.3-350 nM). Nonetheless, CAs IX and XII were the most susceptible isoforms to this class of inhibitors. In particular, compounds bearing an unsubstituted phenyl ring at the pyrazoline 3 position showed 1.3-1.5 nM KIs against CA IX. In contrast, a subset of derivatives having a 4-halo-phenyl at the same position of the aromatic scaffold even reached subnanomolar KIs against CA XII (0.62-0.99 nM). Docking studies with CA IX and XII were used to shed light on the derivative binding mode driving the preferential inhibition of the tumor-associated CAs. The identified potent and selective CA IX/XII inhibitors are of interest as leads for the development of new anticancer strategies.

Isoxazoles-a biocompatible radical scavenging agents: Citrus juice mediated environmentally benign synthesis and characterization

This study demonstrates the efficient eco-friendly synthesis of a series of isoxazole derivatives 5a-h through (3+2) annulation of chalcones 3a-h and hydroxylamine (4) in citrus juice medium. The synthesized compounds were characterized by spectroscopic a

Application of Polyphosphoric Acid-Mediated Acyl Migration for Regiospecific Synthesis of Diverse 2-Acylpyrroles from Chalcones

A metal-free approach for the synthesis of 2-acylpyrroles is reported in this paper. Synthesis of the target molecule started from chalcones and was carried out in two steps. Initial step involved the conversion of chalcones to corresponding 4-substituted-3-acylpyrroles by reaction with TosMIC. In the subsequent step, target molecules were obtained in modest to good yields by polyphosphoric acid-mediated acyl rearrangement of 3-acylpyrroles to their 2-acyl congeners. The crucial final step was amenable to diverse substitutions on pyrrole ring. Preliminary experiment for the determination of mechanism indicated the involvement of acylium ion.

Design and synthesis of novel natural clinoptilolite-MnFe2O4 nanocomposites and their catalytic application in the facile and efficient synthesis of chalcone derivatives through Claisen-Schmidt reaction

A series of three novel nanocomposites were prepared by modifying the surface of natural clinoptilolite using various amounts of manganese ferrite (MnFe2O4) nanoparticles. These manganese ferrite-modified nanocomposites (MFO–NC) were fully characterized by XRD, FT-IR, EDX, VSM and TEM analyses. One of these novel nanocomposites with 40?wt% of manganese ferrite in clinoptilolite (MFO–NC-3) showed a strong catalytic behavior in the aldol-type Claisen–Schmidt reaction for the synthesis of chalcones. A strong catalytic synergy was observed between nano-MnFe2O4 particles and natural clinoptilolite in the structure of these nanocomposites. The products with a broad range of substituents on the reactants were efficiently obtained under room-temperature conditions within relatively short reaction times with good to excellent yields in the presence of one of the prepared MFO–NC nanocomposites. This nanocomposite also showed a strong stability and substantial reusability in the synthesis of chalcones.

Indium(III) triflate-catalyzed reactions of AZA-michael adducts of chalcones with aromatic amines: Retro-michael addition versus quinoline formation

The indium(III) triflate-catalyzed reaction of aza-Michael adducts of chalcones with aromatic amines has been investigated. The Michael adducts derived from substituted anilines and chalcones underwent retro-Michael addition to give the original starting materials, whereas the adducts derived from 1-naphthylamines and chalcones afforded quinolines. A six-membered cyclic transition state has been proposed to explain the retro-Michael addition, while a Povarov mechanism has been put forward to explain the quinoline formation.