60234-90-4

Basic information

• Product Name: 3-Buten-2-one, 4-(3,4-dimethoxyphenyl)-, (3E)-
• CAS NO: 60234-90-4
• Molecular Formula: C12H14O3
• Molecular Weight: 206.241
• Mol File: 60234-90-4.mol
• Article Data: 58

Chemical Properties

• CAS DataBase Reference: 3-Buten-2-one, 4-(3,4-dimethoxyphenyl)-, (3E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Buten-2-one, 4-(3,4-dimethoxyphenyl)-, (3E)-(60234-90-4)
• EPA Substance Registry System: 3-Buten-2-one, 4-(3,4-dimethoxyphenyl)-, (3E)-(60234-90-4)

Safety Data

• Hazardous Substances Data: 60234-90-4(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 67-64-1 acetone 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 110-89-4 piperidine 
• 74-83-9 methyl bromide 
• 1080-12-2 (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-ene-2-one 
• 97387-80-9 1-(3,4-dimethoxy-phenyl)-but-3-en-1-ol 
• 78-94-4 methyl vinyl ketone 
• 6315-89-5 3,4-dimethoxyaniline 
• 1080-12-2 Dehydrozingerone 
• 74-88-4 methyl iodide 
• 121-33-5 vanillin 

Downstream Products

• 52451-39-5 6-(3,4-Dimethoxy-phenyl)-4-ethoxy-2-oxo-cyclohex-3-enecarboxylic acid ethyl ester 
• 76539-81-6 6-(3,4-Dimethoxy-phenyl)-4-pyrrolidin-1-yl-5,6-dihydro-thiopyran-2-thione 
• 76539-80-5 6-(3,4-Dimethoxy-phenyl)-4-piperidin-1-yl-5,6-dihydro-thiopyran-2-thione 
• 76539-79-2 6-(3,4-Dimethoxy-phenyl)-4-morpholin-4-yl-5,6-dihydro-thiopyran-2-thione 
• 130001-13-7 5-(3,4-Dimethoxy-phenyl)-7-methyl-2-thioxo-1,2,3,5-tetrahydro-pyrano[2,3-d]pyrimidin-4-one 
• 130001-12-6 5-(3,4-Dimethoxy-phenyl)-7-methyl-1,3-diphenyl-2-thioxo-1,2,3,5-tetrahydro-pyrano[2,3-d]pyrimidin-4-one 
• 130001-14-8 5-(3,4-Dimethoxy-phenyl)-7-methyl-2-thioxo-1,3-di-o-tolyl-1,2,3,5-tetrahydro-pyrano[2,3-d]pyrimidin-4-one 
• 130001-16-0 5-(3,4-Dimethoxy-phenyl)-1,3-bis-(2-methoxy-phenyl)-7-methyl-2-thioxo-1,2,3,5-tetrahydro-pyrano[2,3-d]pyrimidin-4-one 
• 76539-78-1 4-Diethylamino-6-(3,4-dimethoxy-phenyl)-5,6-dihydro-thiopyran-2-thione 
• 6302-60-9 4-(3,4-dimethoxy-phenyl)-butan-2-one 
• 61696-80-8 3-(3,4-dimethoxyphenyl)-1-tetralone 
• 2316-26-9 3,4-dimethoxycinnamic acid 
• 276681-05-1 (E)-3-tert-butyldimethylsiloxy-1-(3,4-dimethoxyphenyl)-1,3-butadiene 
• 748157-67-7 1-(3,4-dimethoxyphenyl)-3-(trimethylsilyloxy)buta-1,3-diene 

Relevant articles and documents

Novel substituted 5-methyl-4-acylaminoisoxazoles as antimitotic agents: Evaluation of selectivity to LNCaP cancer cells

A series of novel antimitotic agents was designed using the replacement of heterocyclic cores in two tubulin-targeting lead molecules with the acylated 4-aminoisoxazole moiety. Target compounds were synthesized via heterocyclization of β-aryl-substituted vinylketones by tert-butyl nitrite in the presence of water as a key step. 4-Methyl-N-[5-methyl-3-(3,4,5-trimethoxyphenyl)isoxazol-4-yl]benzamide (1aa) was found to stimulate partial depolymerization of microtubules of human lung carcinoma A549 cells at a high concentration of 100 μM and to totally inhibit cell growth (IC50 = 0.99 μM) and cell viability (IC50 = 0.271 μM) in the nanomolar to submicromolar concentration range. These data provide evidence of the multitarget profile of the cytotoxic action of compound 1aa. The SAR study demonstrated that the 3,4,5-trimethoxyphenyl residue is the key structural parameter determining the efficiency both towards tubulin and other molecular targets. The cytotoxicity of 3-methyl-N-[5-methyl-3-(3,4,5-trimethoxyphenyl)isoxazol-4-yl]benzamide (1ab) to the androgen-sensitive human prostate adenocarcinoma cancer cell line LNCaP (IC50 = 0.301 μM) was approximately one order of magnitude higher than that to the conditionally normal cells lines WI-26 VA4 (IC50 = 2.26 μM) and human umbilical vein endothelial cells (IC50 = 5.58 μM) and significantly higher than that to primary fibroblasts (IC50 > 75 μM).

Discovery and Characterization of Pure RhlR Antagonists against Pseudomonas aeruginosa Infections

Pseudomonas aeruginosa (P. aeruginosa) is an opportunistic human pathogen that forms biofilms and produces virulence factors via quorum sensing (QS). Blocking the QS system in P. aeruginosa is an excellent strategy to reduce biofilm formation and the production of virulence factors. RhlR plays an essential role in the QS system of P. aeruginosa. We synthesized 55 analogues based on the chemical structure of 4-gingerol and evaluated their RhlR inhibitory activities using the cell-based reporter strain assay. Comprehensive structure-activity relationship studies identified the alkynyl ketone 30 as the most potent RhlR antagonist. This compound displayed selective RhlR antagonism over LasR and PqsR, strong inhibition of biofilm formation, and reduced production of virulence factors in P. aeruginosa. Furthermore, the survival rate of Tenebrio molitor larvae treated with 30 in vivo greatly improved. Therefore, compound 30, a pure RhlR antagonist, can be utilized for developing QS-modulating molecules in the control of P. aeruginosa infections.

NOVEL SMALL MOLECULES THAT BIND AND/OR MODULATE DIFFERENTFORMS OF TAU OLIGOMERS

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