89246-40-2

Usage

Uses

Used in Pharmaceutical Industry:
N-(3-cyanophenyl)-2-phenylacetamide is used as an effective inhibitor for morbillivirus-induced membrane fusion. Its low cytotoxicity profile allows for its potential use in the development of antiviral therapies, particularly targeting morbilliviruses, which are responsible for severe infectious diseases.

Upstream product

• 2237-30-1 m-cyanoaniline 
• 103-80-0 phenylacetyl chloride 
• 201230-82-2 carbon monoxide 
• 108-88-3 toluene 
• 103-82-2 phenylacetic acid 

Relevant academic research and scientific papers

B(OCH2CF3)3-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether

The use of B(OCH2CF3)3 for mediating direct amidation reactions of a wide range of pharmaceutically relevant carboxylic acids and amines is described, including numerous heterocycle-containing examples. An initial screen of solvents for the direct amidation reaction suggested that cyclopentyl methyl ether, a solvent with a very good safety profile suitable for use over a wide temperature range, was an excellent replacement for the previously used solvent acetonitrile. Under these conditions amides could be prepared from 18 of the 21 carboxylic acids and 18 of the 21 amines examined. Further optimisation of one of the low yielding amidation reactions (36% yield) via a design of experiments approach enabled an 84% yield of the amide to be obtained.

Amide bond formation via C(sp3)-H bond functionalization and CO insertion

An efficient method for the synthesis of amides via Pd-catalyzed oxidative carbonylation of C(sp3)-H bonds with CO and amines is described. The route efficiently provides substituted phenyl amides from alkanes.

Nonpeptide inhibitors of measles virus entry

Measles virus (MV) is one of the most infectious pathogens known. Despite the existence of a vaccine, over 500 000 deaths/year result from MV or associated complications. Anti-measles compounds could conceivably reverse these statistics. Previously, we described a homology model of the MV fusion protein trimer and a putative binding site near the head-neck region. The resulting model permitted the identification of two nonpeptidic entry inhibitors. Here, we present the design, synthesis, and bioevaluation of several series of fusion inhibitors and describe their structure-activity relationships (SAR). Five simply substituted anilides show low-μM blockade of the MV, one of which (AS-48) exhibits IC50 = 0.6-3.0 μM across a panel of wild-type MV strains found in the field. Molecular field topology analysis (MFTA), a 2D QSAR approach based on local molecular properties (atomic charges, hydrogen-bonding capacity and local lipophilicity), applied to the anilide series suggests structural modifications to improve potency.