1448458-89-6

Basic information

• Product Name: (5Z)-5-(4-(dimethylamino)benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
• Synonyms: (5Z)-5-(4-(dimethylamino)benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one
• CAS NO: 1448458-89-6
• Molecular Weight: 445.539
• Mol File: 1448458-89-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (5Z)-5-(4-(dimethylamino)benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5Z)-5-(4-(dimethylamino)benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one(1448458-89-6)
• EPA Substance Registry System: (5Z)-5-(4-(dimethylamino)benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one(1448458-89-6)

Safety Data

• Hazardous Substances Data: 1448458-89-6(Hazardous Substances Data)

Upstream product

• 100-68-5 methyl-phenyl-thioether 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 162011-90-7 rofecoxib 
• 50413-24-6 2-bromo-1-(4-methanesulfonylphenyl)ethanone 
• 10297-73-1 4-(methanesulfonyl)acetophenone 
• 1778-09-2 4-(Methylthio)acetophenone 

Relevant articles and documents

Development of Rofecoxib-Based Fluorescent Probes and Investigations on Their Solvatochromism, AIE Activity, Mechanochromism, and COX-2-Targeted Bioimaging

Cyclooxygenase-2 (COX-2) fluorescent probes are promising tools for early diagnosis of cancer. Traditionally, COX-2 probes were designed by connecting two parts, a fluorophore and a COX-2 binding unit, via a flexible linker. Herein, a new class of COX-2-specific fluorescent probes have been developed via one-step modification from rofecoxib by an integrative approach to combine the binding unit and the fluorophore into one. Among them, several new rofecoxib analogues not only exhibited still potent COX-2 binding ability but also exhibited attractive fluorescence properties, such as tunable blue-red emission, solvatochromism, aggression-induced emission behavior, and mechanochromism. Notably, the emission of2a16can be switched between green-yellow in the crystalline state and red-orange in the amorphous state by grinding and fuming treatments. Furthermore, the highly fluorescent compound2a16(Φf= 0.94 in powder) displayed a much stronger fluorescence imaging of COX-2 in HeLa cancer cells overexpressing COX-2 than RAW264.7 normal cells with a minimal expression of COX-2. Most importantly,2a16can light up human cancer tissues from adjacent normal tissues with a much brighter fluorescence by targeting the COX-2 enzyme. These results demonstrated the potential of2a16as a new red fluorescent probe for human cancer imaging in clinical applications.

Stereoselective synthesis and anti-proliferative effects on prostate cancer evaluation of 5-substituted-3,4-diphenylfuran-2-ones

Series of 5-substituted-3,4-diphenylfuran-2-ones were stereoselectively prepared. Their potential anti-proliferative effects on prostate cancer and some of their cyclooxygenases (COXs) inhibitory activities were evaluated. Structure-activity relationship (SAR) data, acquired by substituent modification at the para-position and ortho-position of the C-3 phenyl ring and 5-substituted modification of the central furanone, showed that 3-(2-chloro-phenyl)-4-(4-methanesulfonyl-phenyl)-5-(1-methoxy-ethyl) -5H-furan-2-one (13p) was the most potent compound and could effectively reduce the proliferation of prostate cancer cells (PC3 cell IC50 = 20 μM; PC3 PCDNA cell IC50 = 5 μM; PC3 SKP2 cell IC50 = 5 μM; DU145 cell IC50 = 25 μM). The cell cycle analysis for 13p in DU145 indicated that 13p may induce G1 phase arrest.