34008-87-2

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 99-92-3 p-aminobenzophenone 
• 556-18-3 4-aminobenzaldehyde 
• 3156-41-0 1-nitro-4-[(E)-2-nitroeth-1-enyl]benzene 

Downstream Products

• 1202546-45-9 1-acetyl-3-(4-aminophenyl)-5-(4-nitrophenyl)-2-pyrazoline 

Relevant academic research and scientific papers

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.

Chalcones and their B-aryl analogues as myeloperoxidase inhibitors: In silico, in vitro and ex vivo investigations

In the present study, a series of chalcones and their B-aryl analogues were prepared and evaluate as inhibitors of myeloperoxidase (MPO) chlorinating activity, using in vitro and ex vivo assays. Among these, B-thiophenyl chalcone (analogue 9) demonstrated inhibition of in vitro and ex vivo MPO chlorinating activity, exhibiting IC50 value of 0.53 and 19.2 μM, respectively. Potent ex vivo MPO inhibitors 5, 8 and 9 were not toxic to human neutrophils at 50 μM, as well as displayed weak 2,2-diphenyl-1-pycrylhydrazyl radical (DPPH?) and hypochlorous acid (HOCl) scavenger abilities. Docking simulations indicated binding mode of MPO inhibitors, evidencing hydrogen bonds between the amino group at 4′position (ring A) of chalcones with Gln91, Asp94, and Hys95 MPO residues. In this regard, the efficacy and low toxicity promoted aminochalcones and arylic analogues to the rank of hit compounds in the search for new non-steroidal anti-inflammatory compounds.

Synthesis, characterization and molecular docking of 1,2,4-triazole derivatives as potential antimicrobial agents

In this study, a new series of (E)-N-(4-(3-(3,5-dialkylphenyl)acryloyl)phenyl)-2-(1H-1,2,4-triazol-1-yl)acetamide (32-41) was synthesized, characterized by FT-IR, 1H NMR, 13C NMR and Mass spectral analysis and evaluated for their in

Antiproliferative activity and p53 upregulation effects of chalcones on human breast cancer cells

Chalcones are valuable structures for drug discovery due to their broad bioactivity spectrum. In this study, we evaluated 20 synthetic chalcones against estrogen-receptor-positive breast cancer cells (MCF-7 line) and triple-negative breast cancer (TNBC) cells (MDA-MB-231 line). Antiproliferative screening by MTT assay resulted in two most active compounds: 2-fluoro-4’-aminochalcone (11) and 3-pyridyl-4’-aminochalcone (17). Their IC50 values ranged from 13.2 to 34.7?μM against both cell lines. Selected chalcones are weak basic compounds and maintained their antiproliferative activity under acidosis conditions (pH 6.7), indicating their resistance to ion-trapping effect. The mode of breast cancer cells death was investigated and chalcones 11 and 17 were able to induce apoptosis rather than necrosis in both lines. Antiproliferative target investigations with MCF-7 cells suggested 11 and 17 upregulated p53 protein expression and did not affect Sp1 protein expression. Future studies on chalcones 11 and 17 can define their in vivo therapeutic potential.

Synthesis and biological evaluation of novel aminochalcones as potential anticancer and antimicrobial agents

A series of 18 aminochalcone derivatives were obtained in yields of 21.5-88.6% by applying the classical Claisen-Schmidt reaction. Compounds 4-9, 14 and 16-18 with 4-ethyl, 4-carboxy-, 4-benzyloxy- and 4-benzyloxy-3-methoxy groups were novel, not previously described in the scientific literature. To determine the biological properties of the synthesized compounds, anticancer and antimicrobial activity assays were performed. Antiproliferative potential was evaluated on four different human colon cancer cell lines-HT-29, LS180, LoVo and LoVo/DX-using the SRB assay and compared with green monkey kidney fibroblasts COS7. Anticancer activity was described as the IC50 value. The best results were observed for 2′-aminochalcone (1), 3′-aminochalcone (2) and 4′-aminochalcone (3) (IC50 = 1.43-1.98 μg·mL-1) against the HT-29 cell line and for amino-nitrochalcones 10-12 (IC50 = 2.77-3.42 μg·mL-1) against the LoVo and LoVo/DX cell lines. Moreover, the antimicrobial activity of all derivatives was evaluated on two strains of bacteria: Escherichia coli ATCC10536 and Staphylococcus aureus DSM799, the yeast strain Candida albicans DSM1386 and three strains of fungi: Alternaria alternata CBS1526, Fusarium linii KB-F1 and Aspergillus Niger DSM1957. In the case of E. coli ATCC10536 almost all derivatives hindered the bacterial growth (ΔOD = 0). Furthermore, the best results were observed in the presence of 4′-aminochalcone (3), that completely limited the growth of all tested strains at the concentration range of 0.25-0.5 mg·mL-1. The strongest bacteriostatic activity was exhibited by novel 3′-amino-4-benzyloxychalcone (14), that prevented the growth of E. coli ATCC10536 with MIC = 0.0625 mg·mL-1

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.].

Design, synthesis and evaluation of chalcones as H1N1 Neuraminidase inhibitors

A series of chalcone derivatives (1a–2i) were designed based on isoliquiritigenin (the most active natural chalcone non-competitive neuraminidase (NA) inhibitor). Molecular modeling studies revealed that isoliquiritigenin and its designed analogs occupied

Synthesis, docking studies and: In vitro evaluation of novel chalcones as potent inhibitors of phosphodiesterase 5 from human platelets and 5A from bovine recombinant

A series of new nitric oxide donor chalcone moieties were synthesized and evaluated for phosphodiesterase 5 (PDE 5) and 5A (PDE 5A) inhibition potential from human plasma and bovine recombinant, respectively. Molecular docking showed an excellent binding