Synthesis of novel 3-pyridinecarbonitriles with amino acid function and their fluorescence properties.
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.
Girgis
A S
AS
Pesticide Chemistry Department, National Research Centre, Dokki, Cairo, Egypt. girgisas10@yahoo.com
Kalmouch
A
A
Hosni
H M
HM
D000596:Amino Acids / Q000737:chemistry*; D002176:Candida albicans / Q000187:drug effects; D005453:Fluorescence; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000596:Amino Acids; D009570:Nitriles; D011725:Pyridines