Synthesis of novel 3-pyridinecarbonitriles with amino acid function and their fluorescence properties

• Published in: Amino acids Vol. 26; no. 2; pp. 139 - 146
• Main Authors: Girgis, A S, Kalmouch, A, Hosni, H M
• Format: Journal Article
• Language: English
• Published: Austria Springer Nature B.V 01.03.2004
• Subjects: Amino acids; Amino Acids - chemistry; Antibacterial materials; Aqueous solutions; Candida albicans - drug effects; Derivatives; Esters; Fluorescence; Gram-Negative Bacteria - drug effects; Gram-Positive Bacteria - drug effects; Microbial Sensitivity Tests; Molecular Structure; Nitriles - chemical synthesis; Nitriles - chemistry; Nitriles - pharmacology; Pyridines; Pyridines - chemical synthesis; Pyridines - chemistry; Pyridines - pharmacology; Refluxing; Synthesis
• ISSN: 0939-4451; 1438-2199
• DOI: 10.1007/s00726-003-0051-7

A variety of N-[(4,6-diaryl-3-pyridinecarbonitrile)-2-yl] amino acid esters 2-4 were synthesized through the reaction of 2-bromo-3-pyridinecarbonitriles 1 with the appropriate alpha-amino acid ester hydrochloride in refluxing dioxane in the presence of triethylamine as dehydrohalogenating agent. Similarly, N'-glycylglycine analogues 5 were obtained through the reaction of 1 with the dipeptide ester. On the other hand, attempts were made towards the construction of amino acid derivatives 7 through the reaction of 1 with aqueous solution alpha-amino acids 6 in refluxing pyridine, but were unsuccessful, and instead the unexpected 2-amino-3-pyridinecarbonitriles 8 were isolated. The fluorescence properties of the newly synthesized pyridines 2-5 were evaluated. Some of the prepared compounds show considerable antibacterial activity.