81384-43-2

Upstream product

• 4410-32-6 N-benzyl-2-hydroxy-2-phenylacetamide 
• 108-24-7 acetic anhydride 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 88333-03-3 Benzyl isocyanide 
• 100-52-7 benzaldehyde 
• 64-19-7 acetic acid 
• 100-46-9 benzylamine 

Downstream Products

• 27946-19-6 N-benzyl-α-chlorophenylacetamide 
• 6109-33-7 4-phenyl-1,4-dihydroisoquinolin-3(2H)-one 
• 1408381-76-9 (4R)-4-phenyl-1,4-dihydroisoquinolin-3(2H)-one 
• 1408382-17-1 (4S)-2-acetyl-4-phenyl-1,4-dihydro-2H-izoquinolin-3-one 
• 1408382-14-8 (4S)-4-phenyl-1,4-dihydroisoquinolin-3(2H)-one 
• 1408382-22-8 (4R)-2-acetyl-4-phenyl-1,4-dihydro-2H-izoquinolin-3-one 
• 1408382-06-8 2-acetyl-4-phenyl-1,4-dihydro-2H-izoquinolin-3-one 
• 89160-45-2 (4R)-(+)-4-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 4410-32-6 N-benzyl-2-hydroxy-2-phenylacetamide 

Relevant academic research and scientific papers

The amine as carbonyl precursor in the chemoenzymatic synthesis of Passerini adducts in aqueous medium

A new simple environmentally friendly protocol based on sequential chemoenzymatic synthesis of α-acyloxy carboxyamides from amines as a carbonyl precursor is presented. For the synthesis of the desired products, biocatalytic process combining laccase/TEMPO oxidation of amine followed by Passerini reaction was developed. After a careful optimization of the reaction conditions only one of desired Passerini reaction products was obtained despite of the presence of two different carboxylic acids in reaction medium. The developed protocol offers a chemoselective and environmentally friendly procedure for the synthesis of various α-acyloxy amides with good to excellent yields.

Solvent-free passerini reactions

The influence of the substrate structure and concentration on the yield of the Passerini reaction was studied. A new, solvent-free methodology for a convenient preparation of α-acyloxyamides 4 was established and compared to the classical methodology. A h

The anticonvulsant activities of functionalized N-benzyl 2-acetamidoacetamides. The importance of the 2-acetamido substituent

Recent studies have demonstrated that substituted N-benzyl 2-acetamidoacetamides provide significant protection against maximal electroshock (MES)-induced seizures in mice and rats. In this study, we investigated whether the 2-acetamido moiety was necessary for anticonvulsant activity. Ten derivatives of the known anticonvulsant, N-benzyl 2-acetamido-2-phenylacetamide were prepared in which the 2-acetamido group was replaced by hydrogen, methyl, oxygen, and halogen substituents. Evaluation of these compounds in the MES-induced seizure test demonstrated that both the hydroxy and the methoxy compounds provided full protection against MES-induced seizures in mice given ip at 100 mg/g. Moreover, evaluation of the individual stereoisomers for the hydroxy compound showed that the principal activity resided in the (R)-isomer. These findings demonstrated that the 2-acetamido substituent is important but not obligatory for the prevention of MES-induced seizures. Further supporting evidence was provided by comparing the pharmacological activities of N-benzyl 2,3-dimethoxypropionamide with N-benzyl 2-acetamido-3-methoxypropionamide. The ED50 value for the former in the MES test was 3.0 mg/kg (ip), which compared favorably with phenobarbital (ED50=22 mg/kg), but the ED50 value for N-benzyl 2-acetamido-3-methoxypropionamide was 8.3 mg/kg.