6308-53-8

Usage

InChI:InChI=1/C19H16N2O3/c22-18(16-11-10-14-8-4-5-9-15(14)20-16)21-17(19(23)24)12-13-6-2-1-3-7-13/h1-11,17H,12H2,(H,21,22)(H,23,24)

Upstream product

• 50342-01-3 quinolin-2-ylcarbonyl chloride 
• 150-30-1 Phenylalanine 
• 93-10-7 quinoline-2-carboxylic acid 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 136465-99-1 2,5-dioxopyrrolidin-1-ylquinoline-2-carboxylate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 

Relevant academic research and scientific papers

A convenient and efficient synthesis of dipeptidyl benzoxaboroles and their peptidomimetics

We have developed a convenient and efficient method for the synthesis of dipeptidyl benzoxaboroles and their peptidomimetics. The novel dipeptidyl benzoxaboroles were obtained by the protecting-group-free coupling of 6-amino-1,3-dihydro-2,1-benzoxaborol-1-ol with various N-(arylcarbonyl) phenylalanines. Bioisosteric replacement of the terminal amide moiety of dipeptidyl benzoxaboroles by 1,3,4-oxadiazoles or 4H-3,1-benzothiazin-4-one provided their peptidomimetics with good molecular diversity. These transformations were based on the pluripotency of methyl (S)-2-isothiocyanato-3- phenylpropanoate and were highlighted by mild reaction conditions, high atom efficiency, and good to excellent isolated yields. This method is a valuable addition to the development of novel drug-like boronic acid molecules. Georg Thieme Verlag Stuttgart ? New York.

Enantioselective solid-phase synthesis of α-amino acid derivatives

Wang-resin bound derivatives of glycine Schiff base esters are alkylated in the presence of quaternary ammonium salts derived from cinchonidine or cinchonine using phosphazene bases to give either enantiomer of the product α-amino acid derivatives in 51-89% ee.

Solid-phase synthesis of unnatural amino acids using unactivated alkyl halides

Conditions were developed for the efficient alkylation of the resin-bound benzophenone imine of glycine with a variety of unreactive alkyl halides. Alkylations were accomplished at room temperature in NMP using the phosphazene-type base, BEMP.

N-Acylphenylalanines and Related Compounds. A New Class of Oral Hypoglycemic Agents

N-Benzoyl-DL-phenylalanine (1) was found to possess hypoglycemic activity.A series of the analogues of compound 1 were prepared and evaluated for their blood glucose lowering activity.Both the steric effects of the phenylalanine moiety and the effects of variations in the acyl moiety were investigated.This study elucidated some of the structure-activity relationships and led to the development of N-(4-ethylbenzoyl)-D-phenylalanine (34), which was 50 times more potent than the initial compound 1.