87657-78-1

Basic information

• Product Name: α-Methyl-3-fluoro-4-phenylbenzeneacetamide
• Synonyms: α-Methyl-3-fluoro-4-phenylbenzeneacetamide
• CAS NO: 87657-78-1
• Molecular Weight: 243.281
• Mol File: 87657-78-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: α-Methyl-3-fluoro-4-phenylbenzeneacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: α-Methyl-3-fluoro-4-phenylbenzeneacetamide(87657-78-1)
• EPA Substance Registry System: α-Methyl-3-fluoro-4-phenylbenzeneacetamide(87657-78-1)

Safety Data

• Hazardous Substances Data: 87657-78-1(Hazardous Substances Data)

Upstream product

• 137361-33-2 α-Methyl-3-fluoro-4-phenylbenzeneacetyl chloride 
• 5104-49-4 fluorobiprofen 
• 56430-76-3 2-(2-fluoro-biphenyl-4-yl)-propionaldehyde 
• 107727-63-9 Sodium; 2-(2-fluoro-biphenyl-4-yl)-1-hydroxy-propane-1-sulfonate 

Downstream Products

• 74648-00-3 α-methyl-(2-fluoro-4-biphenylyl)acetonitrile 
• 42771-79-9 3'-fluoro-4'-phenylacetophenone 

Relevant articles and documents

Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes

Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.

NO-NSAIDs. Part 3: Nitric oxide-releasing prodrugs of non-steroidal anti-inflammatory drugs

In continuation of our efforts to discover novel nitric oxide-releasing non-steroidal anti-inflammatory drugs (NO-NSAIDs) as potentially "Safe NSAIDs," we report herein the design, synthesis and evaluation of 21 new NO-NSAIDs of commonly used NSAIDs such as aspirin, diclofenac, naproxen, flurbiprofen, ketoprofen, sulindac, ibuprofen and indomethacin. These prodrugs have NO-releasing disulfide linker attached to a parent NSAID via linkages such as an ester (compounds 9-16), a double ester (compounds 17-24), an imide (compounds 25-30) or an amide (compounds 31-33). Among these NO-NSAIDs, the ester-containing NO-aspirin (9), NO-diclofenac (10), NO-naproxen (11), and the imide-containing NO-aspirin (25), NO-flurbiprofen (27) and NO-ketoprofen (28) have shown promising oral absorption, anti-inflammatory activity and NO-releasing property, and also protected rats from NSAID-induced gastric damage. NO-aspirin compound 25, on further co-evaluation with aspirin at equimolar doses, exhibited comparable dose-dependent pharmacokinetics, inhibition of gastric mucosal prostaglandin E2 (PGE2) synthesis and analgesic properties to those of aspirin, but retained its gastric-sparing properties even after doubling its oral dose. These promising NO-NSAIDs could therefore represent a new class of potentially "Safe NSAIDs" for the treatment of arthritic pain and inflammation.

Prodrugs containing novel bio-cleavable linkers

The invention provides the compounds of formula (I) or pharmaceutically acceptable salts thereof. The invention also provides pharmaceutical compositions comprising one or more compounds of formula I or intermediates thereof and one more of pharmaceutically acceptable carriers, vehicles or diluents. The invention further provides methods of preparation and methods of use of prodrugs including NO-releasing prodrugs, double prodrugs and mutual prodrugs comprising the compounds of formula I.