914800-39-8

Basic information

• Product Name: (E)-3-(4-Methanesulfonyl-phenyl)-2-(4-methoxy-phenyl)-acrylic acid
• Synonyms: (E)-3-(4-Methanesulfonyl-phenyl)-2-(4-methoxy-phenyl)-acrylic acid
• CAS NO: 914800-39-8
• Molecular Weight: 332.377
• Mol File: 914800-39-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-3-(4-Methanesulfonyl-phenyl)-2-(4-methoxy-phenyl)-acrylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-(4-Methanesulfonyl-phenyl)-2-(4-methoxy-phenyl)-acrylic acid(914800-39-8)
• EPA Substance Registry System: (E)-3-(4-Methanesulfonyl-phenyl)-2-(4-methoxy-phenyl)-acrylic acid(914800-39-8)

Safety Data

• Hazardous Substances Data: 914800-39-8(Hazardous Substances Data)

Upstream product

• 104-01-8 4-Methoxyphenylacetic acid 
• 5398-77-6 para-methanesulfonylbenzaldehyde 

Downstream Products

• 1029146-32-4 2-nitrooxyethyl (E)-2-(4-methoxyphenyl)-3-(4-methanesulfonylphenyl)acrylate 

Relevant articles and documents

Design, synthesis, and biological evaluation of (E)-3-(4-methanesulfonylphenyl)-2-(aryl)acrylic acids as dual inhibitors of cyclooxygenases and lipoxygenases

A group of (E)-3-(4-methanesulfonylphenyl)acrylic acids possessing a substituted-phenyl ring (4-H, 4-Br, 3-Br, 4-F, 4-OH, 4-OMe, 4-OAc, and 4-NHAc) attached to the acrylic acid C-2 position were prepared using a stereospecific Perkin condensation reaction. A related group of compounds having 4- and 3-(4-isopropyloxyphenyl)phenyl, 4- and 3-(2,4-difluorophenyl)phenyl and 4- and 3-(4-methanesulfonylphenyl)phenyl substituents attached to the acrylic acid C-2 position were also synthesized, using a palladium-catalyzed Suzuki cross-coupling reaction, for evaluation as dual cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) inhibitors. (E)-2-(3-Bromophenyl)-3-(4-methanesulfonylphenyl)acrylic acid (9h), and compounds having 4-(4-isopropyloxyphenyl-, 2,4-difluorophenyl-, or 4-methylsulfonylphenyl)phenyl moieties at the acrylic acid C-2 position (11a,b,d), were particularly potent COX-2 inhibitors with a high COX-2 selectivity index (COX-2 IC50 ≈ 0.32 μM, SI > 316) similar to the reference drug rofecoxib (COX-2 IC50 = 0.5 μM, SI > 200). Acrylic acid analogs with a C-2 4-hydoxyphenyl (9d, IC50 = 0.56 μM), or 4-acetamidophenyl (9g, IC50 = 0.11 μM), substituent were particularly potent 5-LOX inhibitors that may participate in an additional specific hydrogen-bonding interaction. A number of compounds possessing a C-2 substituted-phenyl moiety (4-Br, 4-F, and 4-OH), or a 4- or 3-(2,4-difluorophenyl)phenyl moiety, showed potent 15-LOX inhibitory activity (IC50 values in the 0.31-0.49 μM range) relative to the reference drug luteolin (IC50 = 3.2 μM). Compounds having a C-2 4-acetylaminophenyl, or 4-(2,4-difluorophenyl)phenyl, moiety exhibited anti-inflammatory activities that were equipotent to aspirin, but less than that of celecoxib. The structure-activity data acquired indicate the acrylic acid moiety constitutes a suitable scaffold (template) to design novel acyclic dual inhibitors of the COX and LOX isozymes.