126443-09-2

Basic information

• Product Name: (2E)-1-(4-aminophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one
• Synonyms: (2E)-1-(4-aminophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one;(2E)-1-(4-Aminophenyl)-3-[4-(dimethylamino)phenyl]-2-propen-1-one;(E)-1-(4-aminophenyl)-3-(4-dimethylaminophenyl)prop-2-en-1-one;1-(4-aminophenyl)-3-(4-dimethylaminophenyl)prop-2-en-1-one;4'-Amino-4-dimethylaminochalcone;trans-4'-Amino-4-(dimethylamino)chalcone;ZINC05024189
• CAS NO: 126443-09-2
• Molecular Formula: C₁₇H₁₈N₂O
• Molecular Weight: 266.33762
• Mol File: 126443-09-2.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2E)-1-(4-aminophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-(4-aminophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one(126443-09-2)
• EPA Substance Registry System: (2E)-1-(4-aminophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one(126443-09-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 126443-09-2(Hazardous Substances Data)

Usage

Preparation

Synthesis of ADAB: 1-(4-aminophenyl)-3-(4-(dimethylamino)phenyl)prop-2-en-1-one (ADAB):4-aminoacetophenone( 1 g, 6.7 mmol) was suspended in ethanol (20 mL), to the suspension 40% of NaOH and 4-dimethylaminobenzaldeyde(0.904 g, 6.7 mmol) were added and stir this reaction mixture at RT for 16h. After completion of the reaction, the reaction mixture was poured into the 100 mL of ice water and P H is adjusted to 1 by drop wise adding of dil. HCl. The reaction mixture was filtered; the filtrate was neutralized with 5% NaHCO3 and subsequently extracted with CH2Cl2. The organic fraction was concentrated in vacuum under reduced pressure. Yield 1.569 g (86%). 1H NMR (400 MHz, CDCl3) δ, 8.10 (dd, J = 15.6, 8.5 Hz, 2H), 7.98 – 7.69 (m, 1H), 7.59 (dd, J = 8.8, 1.9 Hz, 1H), 7.42 (ddd, J = 15.4, 14.6, 6.7 Hz, 2H), 7.20 – 6.89 (m, 2H), 6.75 (dd, J = 15.5, 8.8 Hz, 2H), 3.26 – 2.91 (m, 6H), 1.64 (s, 2H), 13C NMR (101 MHz, CDCl3) δ 161.34 – 161.14 (m), 130.85 (s), 129.58 (s), 121.45 – 121.25 (m), 111.86 (s), 77.35 (s), 77.03 (s), 76.71 (s), 40.17 (s).

Upstream product

• 99-92-3 p-aminobenzophenone 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 1161-23-5 (E)-3-(4-(N,N-dimethylamino)phenyl)-1-(4-nitrophenyl)prop-2-en-1-one 
• 114569-19-6 N-(4-Hydroxybenzyliden)-4-acetylanilin 

Downstream Products

• 1151741-99-9 2-bromo-N-(4-((E)-3-(4-(dimethylamino)phenyl)acryloyl)phenyl)acrylamide 
• 5336-80-1 N-(4′-[(2E)-3-(4-dimethylaminophenyl)-1-(phenyl)prop-2-en-1-one])acetamide 

Relevant articles and documents

Hydrogen bonding patterns and DFT studies of (4-Acetylphenyl)amino 2,2-Dimethylpropanoate and (E)-1-(4-aminophenyl)-3-[4-(dimethylamino)phenyl] prop-2-en-1-one

The (4-acetylphenyl)amino 2,2-dimethylpropanoate (1) and (E)-1-(4-aminophenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one (2), were synthesized and characterized by elemental analysis, FT-IR, 1H NMR, 13CNMR and single crystal X-ray d

Design, synthesis, docking and biological evaluation of chalcones as promising antidiabetic agents

Diabetes mellitus (DM) is a serious chronic metabolic disorder which occurs due to dysfunction of insulin and therapeutic approaches are poor. It is an under estimation that 387 million people currently suffering globally with diabetic and more than 592 m

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.