25870-75-1

Upstream product

• 99-92-3 p-aminobenzophenone 
• 873-76-7 para-Chlorobenzyl alcohol 
• 100-19-6 (4-nitrophenyl)ethanone 
• 104-88-1 4-chlorobenzaldehyde 
• 25870-65-9 3-(4-chlorophenyl)-1-(4-nitrophenyl)-2-propen-1-one 

Downstream Products

• 27547-07-5 (4-Amino-phenyl)-[3-(4-chloro-phenyl)-oxiranyl]-methanone 
• 131138-76-6 4-(4-Amino-phenyl)-6-(4-chloro-phenyl)-1,6-dihydro-pyrimidine-2-thiol 
• 389636-03-7 4-[5-(4-chloro-phenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-phenylamine 

Relevant academic research and scientific papers

Synthesis and studying of the biological activity of some new coumarin-3-Carboxylic acid heterocyclic derivatives

This study includes the synthesis of a few different coumarin-3-carboxylic acid derivatives of 1,2,3-triazole and triazoline as a starting material. The first step involves the formation of compound (a) in absolute ethanol through the reaction of coumarin

Design, synthesis, and evaluation of different scaffold derivatives against NS2B-NS3 protease of dengue virus

The number of deaths or critical health issues is a threat in the infection caused by Dengue virus, which complicates the situation, as only symptomatic treatment is the current solution. In this regard we have targeted the dengue protease NS2B-NS3 that is responsible for the replication. The series was designed with the help of molecular modeling approach using docking protocols. The series comprised of different scaffolds viz. cinnamic acid analogs (CA1–CA11), chalcone (C1–C10) and their molecular hybrids (Lik1–Lik10), analogs of benzimidazole (BZ1-BZ5), mercaptobenzimidazole (BS1-BS4), and phenylsulfanylmethylbenzimidazole (PS1-PS4). Virtual screening of various natural phytoconstituents was employed to determine the interactions of designed analogs with the residues of catalytic triad in the active site of NS2B-NS3. We have further synthesized the selected leads. The synthesized analogs were evaluated for the cytotoxicity and NS2B-NS3 protease inhibition activity and compared with known anti-dengue natural phytoconstituent quercetin as the standard. CA2, BZ1, and BS2 were found to be more potent and efficacious than the standard quercetin as evident from the protease inhibition assay.

A combined experimental and DFT investigation of mono azo thiobarbituric acid based chalcone disperse dyes

A number of monoazo dyes were synthesized by the reaction of 4-aminoacetophenone with different substituted benzaldehydes to give a new series of chalcone derivatives. The diazonium salts of these chalcones then allowed to react with thiobarbituric acid to produce the appropriate azo dye. The structures of the newly synthesized dyes were assigned by IR, NMR spectral data. IR study confirmed the existence of azo-dioxothioxo tautomer in the solid phase while 1H NMR study indicated the predominance of azoenol-oxothioxo or hydrazo-dioxothioxo tautomers. The geometries of the azo and hydrazo tautomeric forms and their electronic absorption of the dyes were optimized at B3LYP/6-311G level of theory. All the azo compounds were evaluated for their dyeing performance on polyester fibers, and PET. All the synthesized dyes gave moderate to excellent fastness properties on PET fiber. The effects of the nature of the substituents on the color and dyeing properties of these dyes have been evaluated. The mechanism of dyeing polyester fiber was discussed.

Synthesis and antiproliferative activity of chalcone-imide derivatives based on 3,4-dichloro-1h-pyrrole-2,5-dione

A series of chalcone imide derivatives,4'-aminochalcones-based dichloromaleimides,was synthesized from the reaction of 1-(4-acetylphenyl)-3,4-dichloro-1H-pyrrole-2,5-dione with various substituted aldehydes, or by treating 4'- aminochalcone with 3,4-dichlorofuran-2,5-dione in an alternative path. The structures of chalcone imide derivatives were established using IR, 1H NMR, 13C NMR, and mass spectroscopy. Antiproliferative effects of the newly synthesized compounds have been screened on two human cancer types via the MTT assay. Compounds with p-tolyl-1H-pyrrole-2,5-dione, and 4- bromophenyl-1H-pyrrole-2,5-dione derivatives, are highly active on the human liver cancer (HepG-2).On the other hand, all compounds were found to be more effective against breast cancer cells (MCF-7)than the positive control doxorubicin. The results of this work provide a basis for further research of selected chalcone-imide moiety as antiproliferative agents.

Cu(I) mediated hydrogen borrowing strategy for the α-alkylation of aryl ketones with aryl alcohols

Abstract: New triazolium Schiff bases (TSBs) were synthesised via a simple and high throughput process. The new salts were successfully characterised. When reacted with Cu(CH3CN)4PF6, the TSB salts formed mononuclear triazole Schiff base copper(I) complexes and dinuclear complexes that were also characterised. The?copper complexes were generated in situ (mixtures of TSB salts with Cu(CH3CN)4PF6) and applied as homogeneous catalysts for the C–C coupling of a variety of aryl ketones with aryl alcohols, from which?significant reactivity was observed. Reaction conditions were optimised, and the results indicate that the catalyst systems are very robust. A catalyst concentration of 10?mol% efficiently and selectively catalysed the α-alkylation of methyl phenyl ketone and its derivatives to afford up to 94% yield of 1,3-diphenylpropan-1-one and its analogues. The process is adaptable with analogues of acetophenone and benzyl alcohol bearing various regulating substituents tolerated. Graphic abstract: [Figure not available: see fulltext.].

Synthesis of Novel Chalcone-Based L-Homoserine Lactones and Their Quorum Sensing Inhibitory Activity Evaluation

Abstract: Two novel series of chalcone-based homoserine lactones were synthesized and their quorum sensing (QS) inhibitory activity was evaluated against Pseudomonas aeruginosa in vitro. Furthermore these compounds’ capacity for modulation of the LasR-dependent quorum sensing system of P. aeruginosa was identified. Among these compounds, (S)-2-((4-(3-(4-bromo-2-fluorophenyl) acryloyl) phenyl) amino)-N-(2-oxotetrahydrofuran-3-yl)acetamide exerted the inhibition of LasR-dependent QS system of P. aeruginosa in contrast to brominated furanone C30. Worthy of particular note, this research has delivered novel potent quorum sensing inhibitors (QSIs), which strongly inhibit the production of virulence factors in a wild type strain of this pathogenic bacterium.

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.

1,3,4-oxadiazole/chalcone hybrids: Design, synthesis, and inhibition of leukemia cell growth and EGFR, Src, IL-6 and STAT3 activities

A new series of 1,3,4-oxadiazole/chalcone hybrids was designed, synthesized, identified with different spectroscopic techniques and biologically evaluated as inhibitors of EGFR, Src, and IL-6. The synthesized compounds showed promising anticancer activity, particularly against leukemia, with 8v being the most potent. The synthesized compounds exhibited strong to moderate cytotoxic activities against K-562, KG-1a, and Jurkat leukemia cell lines in MTT assays. Compound 8v showed the strongest cytotoxic activity with IC50 of 1.95 μM, 2.36 μM and 3.45 μM against K-562, Jurkat and KG-1a leukemia cell lines, respectively. Moreover; the synthesized compounds inhibited EGFR, Src, and IL-6. Compound 8v was most effective at inhibiting EGFR (IC50 = 0.24 μM), Src (IC50 = 0.96 μM), and IL-6 (% of control = 20%). Additionally, most of the compounds decreased STAT3 activation.

Structure-aided drug development of potential neuraminidase inhibitors against pandemic H1N1 exploring alternate binding mechanism

Abstract: The rate of mutability of pathogenic H1N1 influenza virus is a threat. The emergence of drug resistance to the current competitive inhibitors of neuraminidase, such as oseltamivir and zanamivir, attributes to a need for an alternative approach. The design and synthesis of new analogues with alternate approach are particularly important to identify the potential neuraminidase inhibitors which may not only have better anti-influenza activity but also can withstand challenge of resistance. Five series of scaffolds, namely aurones (1a–1e), pyrimidine analogues (2a–2b), cinnamic acid analogues (3a–3k), chalcones (4a–4h) and cinnamic acid linkages (5a–5c), were designed based on virtual screening against pandemic H1N1 virus. Molecular modelling studies revealed that the designed analogues occupied 430-loop cavity of neuraminidase. Docking of sialic acid in the active site preoccupied with the docked analogues, i.e. in 430-loop cavity, resulted in displacement of sialic acid from its native pose in the catalytic cavity. The favourable analogues were synthesized and evaluated for the cytotoxicity and cytopathic effect inhibition by pandemic H1N1 virus. All the designed analogues resulting in displacement of sialic acid suggested alternate binding mechanism. Overall results indicated that aurones can be measured best among all as potential neuraminidase inhibitor against pandemic H1N1 virus. Graphical abstract: [Figure not available: see fulltext.].

Discovery of novel thienoquinoline-2-carboxamide chalcone derivatives as antiproliferative EGFR tyrosine kinase inhibitors

Novel thienoquinoline carboxamide-chalcone derivatives were prepared via the cyclization of acylated chalcones and 2-mercaptoquinoline-3-carbaldehyde in DMF with K2CO3. Thienoquinolines 9a–f, h exhibited promising antiproliferative effect against all the tested cell lines and gave a significant activity as EGFR inhibitors, with IC50 values ranging from 0.5 and 3.2 μM, and compounds 9e and 9f being the most active of the series. They also showed better activity than Erlotinib against melanoma cancer cell line A375. Moreover, compound 9f influenced pre G1 apoptosis and cell cycle arrest at G2/M phase. The binding mode of the best EGFR inhibitor 9e in the EGFR active site revealed that the thienoquinoline ring occupied the ATP-binding site while the chalcone moiety is located in the allosteric site and is responsible for the enhanced activity of these compounds.