25870-73-9

Basic information

• Product Name: (2E)-1-(4-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• Synonyms: (2E)-1-(4-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
• CAS NO: 25870-73-9
• Molecular Formula: C₁₆H₁₅NO₂
• Molecular Weight: 253.3
• Mol File: 25870-73-9.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 471.5 °C at 760 mmHg
• Flash Point: 232.1 °C
• Appearance: /
• Density: 1.172
• Vapor Pressure: 4.64E-09mmHg at 25°C
• Refractive Index: 1.641
• CAS DataBase Reference: (2E)-1-(4-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(4-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one(25870-73-9)
• EPA Substance Registry System: (2E)-1-(4-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one(25870-73-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 25870-73-9(Hazardous Substances Data)

Usage

General Description

(2E)-1-(4-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one is a chemical compound with the molecular formula C15H15NO2. It is an organic compound with a yellow crystalline appearance. This chemical is known for its use in the synthesis of pharmaceuticals and other organic compounds. It has also been studied for its potential biological activities, including its role as an anti-inflammatory and anti-cancer agent. Additionally, it is used in the production of dyes and pigments due to its aromatic properties. Overall, (2E)-1-(4-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one is a versatile compound with various potential applications in the field of chemistry and medicine.

InChI:InChI=1/C16H15NO2/c1-19-15-9-2-12(3-10-15)4-11-16(18)13-5-7-14(17)8-6-13/h2-11H,17H2,1H3/b11-4+

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 99-92-3 p-aminobenzophenone 
• 100-19-6 (4-nitrophenyl)ethanone 
• 6552-62-1 3-(4-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one 

Downstream Products

• 85791-65-7 acetic acid-[4-(4-methoxy-cinnamoyl)-anilide] 
• 188291-61-4 4-[5-(4-Methoxy-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-phenylamine 
• 1334629-45-6 4-(5-(4-methoxyphenyl)-2-sulfamoyl-5H-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-yl)benzenamine 
• 1415031-43-4 4-acetamido-N-(4-(1-acetyl-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenyl)benzsulphonamide 
• 25870-85-3 1-(4-isothiocyanatophenyl)-3-(4-methoxyphenyl)-2-propen-1-one 

Relevant articles and documents

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.

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.

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.].