184774-58-1

Basic information

• Product Name: (2E)-1-(4-aminophenyl)-3-(2-furyl)prop-2-en-1-one
• Synonyms: (2E)-1-(4-aminophenyl)-3-(2-furyl)prop-2-en-1-one;(E)-1-(4-aminophenyl)-3-(2-furyl)prop-2-en-1-one;(E)-1-(4-aminophenyl)-3-furan-2-yl-prop-2-en-1-one;(E)-1-(4-aminophenyl)-3-furan-2-ylprop-2-en-1-one;1-(4-aminophenyl)-3-(2-furyl)prop-2-en-1-one;1-(4-aminophenyl)-3-furan-2-yl-prop-2-en-1-one;1-(4-aminophenyl)-3-furan-2-ylprop-2-en-1-one;ZINC04159685
• CAS NO: 184774-58-1
• Molecular Formula: C13H11NO2
• Molecular Weight: 213.23194
• Mol File: 184774-58-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2E)-1-(4-aminophenyl)-3-(2-furyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(4-aminophenyl)-3-(2-furyl)prop-2-en-1-one(184774-58-1)
• EPA Substance Registry System: (2E)-1-(4-aminophenyl)-3-(2-furyl)prop-2-en-1-one(184774-58-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 184774-58-1(Hazardous Substances Data)

Upstream product

• 98-01-1 furfural 
• 99-92-3 p-aminobenzophenone 

Downstream Products

• 276680-09-2 2-Amino-6-(4-amino-phenyl)-4-furan-2-yl-nicotinonitrile 

Relevant articles and documents

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.

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.

Crystal structure, FT-Raman and FTIR spectra and DFT calculations of chalcone (2E)-1-(4-aminophenyl)-3-(furan-2-yl)prop-2-en-1-one monohydrate

In this work we present a study of the structural and vibrational properties of the chalcone (2E)-1-(4-aminophenyl)-3-(furan-2-yl)prop-2-en-1-one monohydrate, C13H11O2N·H2O, a strong candidate for fluorescent pr

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, structural characterization, and cytotoxic evaluation of chalcone derivatives

Chalcones containing amino or acetamide groups on ring A and electron donating/withdrawing groups on ring B have been shown to have great cytotoxic potential against human cancer cell lines. In this work, a series of twenty chalcones, including nine 1-(4′-aminophenyl)-3-(substituted aryl)-2-propen-1-ones (1–9), nine 1-(4′-acetamidophenyl)-3-(substituted aryl)-2-propen-1-ones (1a–9a), and two 1-(3′-methoxy-4′-hydroxyphenyl)-3-(substituted aryl)-2-propen-1-ones (10, 11), were synthesized and submitted for initial biological screening using HCT-116 cells. Among the evaluated compounds, chalcone 6a showed strong and selective activity against HCT-116 cells (IC50 = 2.37 ± 0.73 μM). The preliminary structure–activity relationship analysis indicated that the cytotoxic effect of these compounds might be attributed to the combined effect of two electron withdrawing groups: the nitro group (NO2) at the meta-position of ring B and the acetyl group at the para-position of ring A. Moreover, chalcone 6a was able to induce G2/M cell cycle arrest and apoptosis at a concentration of 10 μM after 24 h of incubation. These data reinforce that compound 6a could be a promising lead compound for the future exploration of selective anti-colon carcinoma cancer agents.

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 antibacterial evaluation of novel cationic chalcone derivatives possessing broad spectrum antibacterial activity

There is an urgent need to identify new antibiotics with novel mechanisms that combat antibiotic resistant bacteria. Herein, a series of chalcone derivatives that mimic the essential properties of cationic antimicrobial peptides were designed and synthesized. Antibacterial activities against drug-sensitive bacteria, including Staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Salmonella enterica, as well as clinical multiple drug resistant isolates of methicillin-resistant S. aureus (MRSA), KPC-2-producing and NDM-1-producing Carbapenem-resistant Enterobacteriaceae were evaluated. Representative compounds 5a (MIC: 1 μg/mL against S. aureus, 0.5 μg/mL against MRSA) and 5g (MIC: 0.5 μg/mL against S. aureus, 0.25 μg/mL against MRSA) showed good bactericidal activity against both Gram-positive and Gram-negative bacteria, including the drug-resistant species MRSA, KPC and NDM. These membrane-active antibacterial compounds were demonstrated to reduce the viable cell counts in bacterial biofilms effectively and do not induce the development of resistance in bacteria. Additionally, these representative molecules exhibited negligible toxicity toward mammalian cells at a suitable concentration. The combined results indicate that this series of cationic chalcone derivatives have potential therapeutic effects against bacterial infections.

Antiproliferative and pro-apoptotic activities of 2′- and 4′-aminochalcones against tumor canine cells

In the present study, a series of 2′- and 4′-aminochalcones were synthesized and their antiproliferative activity against a canine malignant histiocytic cell line (DH82) was evaluated. Particularly aminochalcones with a hydrophobic substituent on ring B proved to be potent antiproliferative agents. Among these compounds, aminochalcones 3, 4 and 11 inhibited the growth of DH82 cells, with IC50 values of 34.4, 31.4 and 38.2 μM, respectively, and were three times more potent than etoposide (IC50 = 95.5 μM). The selected chalcones induced death through apoptosis rather than necrosis in DH82 and non-tumorigenic Madin-Darby canine kidney cells (MDCK). Further experiments suggested that the aminochalcones interfere with the regulation of oncogenes/tumor suppressor genes. Aminochalcone 11 inhibited transcription of the TOPOIIα and TP53 genes and aminochalcone 4 down-regulated Sp1 protein expression in a concentration-dependent manner.

Effect of solvent polarity on the photophysical properties of chalcone derivatives

The absorption and fluorescence characteristics of (E)-3-(furan-2-yl)-1-(4-nitrophenyl)prop-2-en-1-one (FNPO), (E)-1-(4-aminophenyl)-3-(furan-2-yl)prop-2-en-1-one (AFPO) and (E)-3-(furan-2-yl)-1-(2-hydroxyphenyl)prop-2-en-1-one (FHPO) were recorded in eig

Design and synthesis of new coumarin–chalcone/NO hybrids of potential biological activity

Abstract: This study aims at investigating a synthesis approach based on molecular hybridization strategy through grafting an nitric oxide-releasing moiety, oxime, to coumarin–chalcone hybrids. In vitro anti-proliferative activity of some of the prepared compounds showed moderate activity (growth inhibition values = 45.85, 40.86, 39.25 for compound 8a against leukemia, Central Nervous system and breast cancer cells, respectively). Also, IC50 = 9.62 and 14.40 for compounds 8h and 8f, respectively against breast Michigan Cancer Foundation-7 cell lines. The antibacterial screening results suggest a possible role for nitric oxide in enhancement of the antibacterial activity where nitric oxide is not the only factor but other factors like physicochemical properties should be investigated for their potential role on the activity.