131868-10-5

Basic information

• Product Name: N-(4-methoxyphenyl)-3-(4-nitrophenyl)prop-(2E)-enamide
• Synonyms: N-(4-methoxyphenyl)-3-(4-nitrophenyl)prop-(2E)-enamide
• CAS NO: 131868-10-5
• Molecular Weight: 298.298
• Mol File: 131868-10-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(4-methoxyphenyl)-3-(4-nitrophenyl)prop-(2E)-enamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-methoxyphenyl)-3-(4-nitrophenyl)prop-(2E)-enamide(131868-10-5)
• EPA Substance Registry System: N-(4-methoxyphenyl)-3-(4-nitrophenyl)prop-(2E)-enamide(131868-10-5)

Safety Data

• Hazardous Substances Data: 131868-10-5(Hazardous Substances Data)

Upstream product

• 104-94-9 4-methoxy-aniline 
• 22440-58-0 (E)-4-nitrocinnamic acid chloride 
• 61916-60-7 3-((4-methoxyphenyl)amino)-3-oxopropanoic acid 
• 882-06-4 4-nitro-trans-cinnamic acid 

Downstream Products

• 1615697-69-2 (E)-3-(4-aminophenyl)-N-(4-methoxyphenyl)acrylamide 
• 1615697-37-4 2-bromo-N-(4-{(1E)-3-oxo-3-[(4-methoxyphenyl)amino]prop-1-en-1-yl}phenyl)acrylamide 

Relevant articles and documents

An alternative way to analogues of avenanthramides and their antiradical activity

Abstract: The paper is devoted to the synthesis of arylidene malonic acid monoanilides and cinnamoyl anilines by condensation of malonic acid monoanilides with aromatic aldehydes. The presented synthetic route applies simple, cheap, and commercially available aromatic aldehydes and amines, thus overcoming traditional schemes, which involve derivatives of hydroxycinnamic acids. Besides, a mild and effective pyridine-mediated decarboxylation of carboxylic group at Csp2 in arylidene malonic acid monoanilides leading to cinnamoyl anilines is presented. The structures of obtained selected arylidene derivatives were approved additionally by X-ray analysis. The antiradical properties (2,2-diphenyl-1-picrylhydrazyl and galvinoxyl tests) and structure–activity relationships of the synthesized compounds were studied. Graphical abstract: [Figure not available: see fulltext.].

Design, synthesis and biological evaluation of arylcinnamide hybrid derivatives as novel anticancer agents

The combination of two pharmacophores into a single molecule represents one of the methods that can be adopted for the synthesis of new anticancer molecules. A series of novel antiproliferative agents designed by a pharmacophore hybridization approach, combining the arylcinnamide skeleton and an α-bromoacryloyl moiety, was synthesized and evaluated for its antiproliferative activity against a panel of seven human cancer cell lines. In addition, the new derivatives were also active on multidrug-resistant cell lines over-expressing P-glycoprotein. The biological effects of various substituents on the N-phenyl ring of the benzamide portion were also described. In order to study the possible mechanism of action, we observed that 4p slightly increased the Reactive Oxygen Species (ROS) production in HeLa cells, but, more importantly, a remarkable decrease of intracellular reduced glutathione content was detected in treated cells compared with controls. These results were confirmed by the observation that only thiol-containing antioxidants were able to significantly protect the cells from induced cell death. Altogether our results indicate that the new derivatives are endowed with good anticancer activity in vitro, and their properties may result in the development of new cancer therapeutic strategies.