5336-80-1

Basic information

• Product Name: N-(4-{(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl}phenyl)acetamide
• Synonyms: acetamide, N-[4-[(2E)-3-[4-(dimethylamino)phenyl]-1-oxo-2-propen-1-yl]phenyl]-
• CAS NO: 5336-80-1
• Molecular Formula: C₁₉H₂₀N₂O₂
• Molecular Weight: 308.3743
• Mol File: 5336-80-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 559.9°C at 760 mmHg
• Flash Point: 292.4°C
• Density: 1.181g/cm³
• Vapor Pressure: 1.44E-12mmHg at 25°C
• Refractive Index: 1.654
• CAS DataBase Reference: N-(4-{(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl}phenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-{(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl}phenyl)acetamide(5336-80-1)
• EPA Substance Registry System: N-(4-{(2E)-3-[4-(dimethylamino)phenyl]prop-2-enoyl}phenyl)acetamide(5336-80-1)

Safety Data

• Hazardous Substances Data: 5336-80-1(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 126443-09-2 1-(4-aminophenyl)-3-<4-(dimethylamino)phenyl>prop-2-en-1-one 
• 99-92-3 p-aminobenzophenone 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 2719-21-3 4-(N-acetylamino)acetophenone 

Relevant articles and documents

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.

4′-Acetamidochalcone derivatives as potential antinociceptive agents

Nine acetamidochalcones were synthesized and evaluated as antinociceptive agents using the mice writhing test. Given intraperitoneally all the compounds were more effective than the two reference analgesic drugs (acetylsalicylic acid and acetaminophen) used for comparison. N-{4-[(2E)-3-(4-nitrophenyl)prop-2- enoyl]phenyl}acetamide (6) was the most effective compound and was therefore selected for more detailed studies. It caused dose-related inhibition in the writhing test, being about 32 to 34-fold more potent than the standard drugs. It was also effective in the second phase of the formalin test and the capsaicin test. These acetamidochalcones, especially compound 6, might be further used as models to obtain new and more potent analgesic drugs.