25893-50-9

Basic information

• Product Name: N-(2-Fluorophenyl)cinnaMaMide
• Synonyms: N-(2-Fluorophenyl)cinnaMaMide
• CAS NO: 25893-50-9
• Molecular Formula: C₁₅H₁₂FNO
• Molecular Weight: 241.2602832
• Mol File: 25893-50-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 424.6°Cat760mmHg
• Flash Point: 210.6°C
• Appearance: /
• Density: 1.233g/cm³
• Vapor Pressure: 2.05E-07mmHg at 25°C
• Refractive Index: 1.65
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.89±0.70(Predicted)
• CAS DataBase Reference: N-(2-Fluorophenyl)cinnaMaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-Fluorophenyl)cinnaMaMide(25893-50-9)
• EPA Substance Registry System: N-(2-Fluorophenyl)cinnaMaMide(25893-50-9)

Safety Data

• Hazardous Substances Data: 25893-50-9(Hazardous Substances Data)

Usage

General Description

"N-(2-Fluorophenyl)cinnamamide" is a chemical compound that is often used in scientific and industrial applications. The chemical formula is C16H13FNO and its molecular weight is 253.277 g/mol. It is part of the cinnamamide family, indicating that it is structurally similar to cinnamic acid. Cinnamamides, including this compound, are often used in the development of new therapeutic agents in pharmaceutical research. An important feature of N-(2-Fluorophenyl)cinnamamide is the presence of a fluorine atom, which often improves the bioavailability and metabolic stability of pharmaceutical agents. Detailed information on its toxicity and environmental impact is not readily available, and it is recommended that appropriate precautions are taken when handling this compound.

InChI:InChI=1/C15H12FNO/c16-13-8-4-5-9-14(13)17-15(18)11-10-12-6-2-1-3-7-12/h1-11H,(H,17,18)/b11-10+

Upstream product

• 348-54-9 2-Fluoroaniline 
• 621-82-9 Cinnamic acid 
• 102-92-1 cinnamoyl chloride 

Downstream Products

• 71738-83-5 2-hydroxy-8-fluoroquinoline 
• 71738-83-5 8-fluoroquinolin-2(1H)-one 
• 25893-56-5 8-fluoro-4-phenyl-3,4-dihydro-1H-quinolin-2-one 
• 1453188-54-9 2-(2-fluorophenyl)-5-phenyl-1,2,4,5-tetrahydro-2-benzazepin-3-one 

Relevant articles and documents

Investigation of anti-inflammatory potential of N-arylcinnamamide derivatives

A series of sixteen ring-substituted N-arylcinnamanilides, previously described as highly antimicrobially effective against a wide spectrum of bacteria and fungi, together with two new derivatives from this group were prepared and characterized. Moreover, the molecular structure of (2E)-N-(2-bromo-5-fluorophenyl)-3-phenylprop-2-enamide as a model compound was determined using single-crystal X-ray analysis. All the compounds were tested for their anti-inflammatory potential, and most tested compounds significantly attenuated the lipopolysaccharide-induced NF-κB activation and were more potent than the parental cinnamic acid. (2E)-N-[2-Chloro-5-(trifluoromethyl)phenyl]-3-phenylprop-2-enamide, (2E)-N-(2,6-dibromophenyl)-3-phenylprop-2-enamide, and (2E)-N-(2,5-dichlorophenyl)-3-phenylprop-2-enamide demonstrated the highest inhibition effect on transcription factor NF-κB at the concentration of 2 μM and showed a similar effectiveness as the reference drug prednisone. Several compounds also decreased the level of TNF-α. Nevertheless, subsequent tests showed that the investigated compounds affect neither IκBα level nor MAPKs activity, which suggests that the N-arylcinnamanilides may have a different mode of action to prednisone. The modification of the C(2,5)0 or C(2,6)0 positions of the anilide core by rather lipophilic and bulky moieties seems to be preferable for the anti-inflammatory potential of these compounds.

Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors

Four series of acid amides were synthesized, and through measurement using a fluorogenic substrate assay with human recombinant MMP-1, MMP-2 and MMP-9, compound 3f showed considerable inhibitory activities against MMP-2, MMP-9 and the best selectivity over MMP-1. Preliminary structure-activity relationship analysis indicated that caffeic acid amides with electron-donating groups at para-position of amino phenyl group showed better inhibitory activities and selectivity than those with electron-withdrawing groups, and the presence of adjacent dihydroxy in the caffeoyl group was very important for the MMP-2 and MMP-9 inhibitory activities.