127172-22-9

Basic information

• Product Name: 1-(3,4-diMethoxyphenyl)-3-(diMethylaMino)prop-2-en-1-one
• Synonyms: 1-(3,4-diMethoxyphenyl)-3-(diMethylaMino)prop-2-en-1-one;1-(3,4-Dimethoxyphenyl)-3-(dimethylamino)-2-propen-1-one;(E)-1-(3,4-dimethoxyphenyl)-3-dimethylamino-prop-2-en-1-one;(E)-1-(3,4-dimethoxyphenyl)-3-dimethylaminoprop-2-en-1-one;6R-0043;MLS000546453;SMR000179851;ZINC01394484
• CAS NO: 127172-22-9
• Molecular Formula: C₁₃H₁₇NO₃
• Molecular Weight: 235.27898
• Mol File: 127172-22-9.mol
• Article Data: 30

Chemical Properties

• Melting Point: 124-125℃
• Boiling Point: 352.9 °C at 760 mmHg
• Flash Point: 167.2 °C
• Appearance: /
• Density: 1.072 g/cm³
• CAS DataBase Reference: 1-(3,4-diMethoxyphenyl)-3-(diMethylaMino)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-diMethoxyphenyl)-3-(diMethylaMino)prop-2-en-1-one(127172-22-9)
• EPA Substance Registry System: 1-(3,4-diMethoxyphenyl)-3-(diMethylaMino)prop-2-en-1-one(127172-22-9)

Safety Data

• Hazardous Substances Data: 127172-22-9(Hazardous Substances Data)

Usage

General Description

1-(3,4-Dimethoxyphenyl)-3-(dimethylamino)prop-2-en-1-one, also known as 3,4-Dimethoxy-α,β-dimethylphenethylamine, is a chemical compound with a complex molecular structure. It is commonly used in scientific research and pharmaceutical development, with potential applications in the fields of medicine and biotechnology. The compound possesses both an alpha, beta-unsaturated ketone and a dimethylamino group, making it a versatile building block for synthesizing a wide range of organic compounds. It also has the potential to exhibit interesting pharmacological properties, potentially serving as a lead compound for the development of new drugs. However, further research and investigation are necessary to fully understand and harness the potential of this complex chemical compound.

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 78558-43-7 6-(3,4-dimethoxyphenyl)-3-cyano-1,2-dihydro-2-oxopyridine 
• 1203608-48-3 5-(3,4-dimethoxyphenyl)-1-phenylpyrazole 
• 1036272-02-2 (Z)-3-chloro-3-(3,4-dimethoxyphenyl)acrylaldehyde 
• 1254339-34-8 (6,7-dichloro-5-hydroxy-benzofuran-3-yl)-(3,4-dimethoxy-phenyl)-methanone 
• 1254339-30-4 (6,7-dibromo-5-hydroxy-benzofuran-3-yl)-(3,4-dimethoxy-phenyl)-methanone 
• 17249-66-0 (3,4-dimethoxyphenyl)(5-hydroxy-benzofuran-3-yl)methanone 
• 1254340-16-3 (3,4-dimethoxy-phenyl)-(5-hydroxy-naphtho[1,2-b]furan-3-yl)-methanone 
• 625370-79-8 6-(3,4-dimethoxyphenyl)-3-cyanopyridine-2-(1H)-thione 

Relevant articles and documents

Novel sulfonamide derivatives carrying a biologically active 3,4-dimethoxyphenyl moiety as VEGFR-2 inhibitors

Novel sulfonamides 3-19 with a biologically active 3,4-dimethoxyphenyl moiety were designed and synthesized. The structures of the synthesized compounds were established using elemental analyses, IR, 1H-NMR, 13C-NMR spectral data and mass spectroscopy. All the synthesized compounds were evaluated for their in vitro anticancer activity against four cancer cell lines, namely human hepatocellular carcinoma (HepG2), human medulloblastoma (Daoy), human cervical cancer (HeLa), and human colon cancer (HT-29), by using a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and dasatinib as the reference drug. Among the tested derivatives, compounds 4, 10, 16, and 19 showed good activity as cytotoxic agents. The most active derivatives were evaluated for their ability to inhibit vascular endothelial growth factor receptor (VEGFR)-2. Compounds Z-4-(3-(3,4-dimethoxyphenyl)-3-oxoprop-1-enylamino)-N-(5-methyl-1,3,4-thiadiazol-2-yl)-benzenesulfonamide 10 and Z-4-(3-(3,4-dimethoxyphenyl)-3-oxoprop-1-enylamino)-N-(1H-indazol-6-yl)-benzenesulfonamide 19 were more active as VEGFR-2 inhibitors than dasatinib. Molecular docking of the most active derivatives on the active site of VEGFR-2 revealed that compound 19 exhibited favorable and promising results.

DDQ-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene

An efficient 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-mediated oxidative coupling reaction of N,N-dimethyl enaminones with cycloheptatriene is developed. It provides a variety of α-alkenylated 1,3-dicarbonyl compounds in moderate to good yields under mild conditions.

Discovery of highly potent tubulin polymerization inhibitors: Design, synthesis, and structure-activity relationships of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidines

By removing 5-methyl and 6-acetyl groups in our previously reported compound 3, we designed a series of novel 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine derivatives as potential tubulin polymerization inhibitors. Among them, compound 5e displayed low nanomolar antiproliferative efficacy on HeLa cells which was 166-fold higher than the lead analogue 3. Interestingly, 5e displayed significant selectivity in inhibiting cancer cells over HEK-293 (normal human embryonic kidney cells). In addition, 5e dose-dependently arrested HeLa in G2/M phase through the alterations of the expression levels of p-cdc2 and cyclin B1, and caused HeLa cells apoptosis by regulation of expressions of cleaved PARP. Further evidence demonstrated that 5e effectively inhibited tubulin polymerization and was 3-fold more powerful than positive control CA-4. Moreover, molecular docking analysis indicated that 5e overlapped well with CA-4 in the colchicine-binding site. These studies demonstrated that 2,7-diaryl-[1,2,4]triazolo[1,5-a]pyrimidine skeleton might be used as the leading unit to develop novel tubulin polymerization inhibitors as potential anticancer agents.

Synthesis and in vitro evaluation of piperazinyl-ureido sulfamates as steroid sulfatase inhibitors

Two new piperazinyl-ureido single ring aryl sulfamate-based inhibitor series were designed against the emerging oncology drug target steroid sulfatase (STS), for which there are existing potent steroidal and non-steroidal agents in clinical trials. 4-(Pip