134430-90-3

Basic information

• Product Name: (E)-N-(4-nitrophenyl)cinnamamide
• Synonyms: (E)-N-(4-nitrophenyl)cinnamamide
• CAS NO: 134430-90-3
• Molecular Weight: 268.272
• Mol File: 134430-90-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (E)-N-(4-nitrophenyl)cinnamamide(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-N-(4-nitrophenyl)cinnamamide(134430-90-3)
• EPA Substance Registry System: (E)-N-(4-nitrophenyl)cinnamamide(134430-90-3)

Safety Data

• Hazardous Substances Data: 134430-90-3(Hazardous Substances Data)

Upstream product

• 100-01-6 4-nitro-aniline 
• 102-92-1 Cinnamoyl chloride 
• 140-10-3 (E)-3-phenylacrylic acid 
• 102-92-1 cinnamoyl chloride 

Downstream Products

• 16618-72-7 3-phenyl-1-indanone 
• 100411-13-0 N-benzyl-N-(4-aminophenyl)-3-phenylacrylamide 
• 14309-92-3 N-benzyl-4-nitroaniline 
• 1453188-51-6 2-(4-aminophenyl)-5-phenyl-1,2,4,5-tetrahydro-2-benzazepin-3-one 
• 17272-83-2 N¹-benzyl-benzene-1,4-diamine 
• 85662-98-2 3-(3',4'-dichlorophenyl)-indan-1-one 
• 74941-74-5 1-(4-Nitrophenyl)-5-styryltetrazole 

Relevant articles and documents

METHOD FOR SYNTHESISING AMIDES

The present invention relates to a method for synthesising amides that is of general applicability. The method may be performed in vitro or in vivo. Cell lines for use in the in vivo methods also form aspects of the invention. The method for synthesising a non-natural amide comprises: a. reaction of a carboxylic acid with a naturally occurring CoA ligase or a variant thereof; and b. reaction of the product of step a with an amine in the presence of a naturally occurring acyltransferase or a variant thereof; with the proviso that where the CoA ligase and acyltransferase are both naturally occurring, they are not derived from the same source species and do not act sequentially in a metabolic pathway; and with the proviso that the non-natural product is not N-(E)-p-coumaroyl-3-hydroxyanthranilic acid or N-(E)-p-caffeoyl-3-hydroxyanthranilic acid. Further, a method for producing an active pharmaceutical ingredient by the aforementioned method and host cells for carrying out said methods are envisaged.

Synthesis of Cinnamanilide Derivatives and Their Antioxidant and Antimicrobial Activity

The amide derivatives of cinnamic acid were synthesized and their antimicrobial and antioxidant activities were investigated. The investigation of antimicrobial potentials of the compounds demonstrated a strong activity against 21 bacterial strains comprising Gram-positive and Gram-negative bacteria. Compounds 2a, 2b, and 3b showed strong antimicrobial activity against all microorganisms with the pMIC value ranging from 2.45 to 3.68. Compounds 2a, 3a, and 3b demonstrated strong antioxidant activity with % inhibition of the DPPH radical of 51% (±1.14), 41% (±1.01), and 50% (±1.23), respectively. These findings indicate that the amide derivatives of the cinnamic acid possess strong antibacterial and antioxidant activities.

Nucleophilic substitution reactions of cinnamoyl chlorides with anilines in acetonitrile and acetonitrile-methanol mixtures

Kinetic studies on the solvolysis (in MeOH-MeCN mixtures) and aminolysis (with anilines in MeCN) of cinnamoyl chlorides have been carried out at 25.0 deg C.The relatively large negative values of ρY+ = -0.9 ca. -1.5 for the methanolysis are consistent with a dissociative SN2-like mechanism.For the aminolysis, the ρy values are positive (ρY = 0.52 ca. 1.64) and ρX values range from -1.68 to -2.51 in acetonitrile.The positive values of βX = 0.6-0.9 and ρXY = 0.88 in acetonitrile, and isotope effect data suggest that the aminolysis proceeds by a stepwise mechanism with rate-limiting breakdown of the tetrahedral intermediate, T+/-.It is noted that in the acyl-transfer reactions proceeding by rate-limiting departure of the leaving group from the tetrahedral intermediate the signs of both ρY and ρXY are positive and the reactivity-selectivity principle (RSP) is valid in general.