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

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

Uses

Used in Pharmaceutical Research:
N-(2-Fluorophenyl)cinnamamide is utilized as a key component in the development of new therapeutic agents. Its unique structure, including the fluorine atom, contributes to improved bioavailability and metabolic stability, making it a promising candidate for pharmaceutical applications.
Used in Drug Design and Development:
In the pharmaceutical industry, N-(2-Fluorophenyl)cinnamamide serves as a valuable building block for designing and developing innovative drugs. Its structural similarity to cinnamic acid and the beneficial effects of the fluorine atom allow for the creation of compounds with enhanced pharmacological properties, potentially leading to more effective treatments for various diseases and conditions.

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.

Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines

We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.

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.

TRIAZOLOPYRIDINE COMPOUNDS AS PIM KINASE INHIBITORS

Compounds of Formula (I), in which A, B, R1, R1a, R2, R3, R4, R5, R6, and R7 have the meanings given in the specification, are receptor tyrosine inhibitors useful in the treatment of immune cell-associated diseases and disorders, such as inflammatory and autoimmune diseases.