Relationship between Structure and Antibacterial Activity of α-Aminophosphonate Derivatives Obtained via Lipase-Catalyzed Kabachnik-Fields Reaction

• Published in: Materials Vol. 15; no. 11; p. 3846
• Main Authors: Koszelewski, Dominik, Kowalczyk, Paweł, Śmigielski, Paweł, Samsonowicz-Górski, Jan, Kramkowski, Karol, Wypych, Aleksandra, Szymczak, Mateusz, Ostaszewski, Ryszard
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 27-05-2022; MDPI
• Subjects: Amines; Antibiotics; antimicrobial activity; Antimicrobial agents; Aromatic compounds; Cytotoxicity; E coli; Enzymes; Inorganic salts; Kabachnik−Fields reaction; Lipase; Microorganisms; Pharmaceutical industry; Substrates; α-aminophosphonates; α-aminophosphonates; Kabachnik−Fields reaction; antimicrobial activity
• ISSN: 1996-1944; 1996-1944
• DOI: 10.3390/ma15113846

We reported a new method dealing with the synthesis of novel pharmacologically relevant α-aminophosphonate derivatives via a lipase-catalyzed Kabachnik−Fields reaction with yields of up to 93%. The advantages of this protocol are excellent yields, mild reaction conditions, low costs, and sustainability. The developed protocol is applicable to a range of H-phosphites and organic amines, providing a wide substrate scope. A new class of α-aminophosphonate analogues possessing P-chiral centers was also synthesized. The synthesized compounds were characterized on the basis of their antimicrobial activities against E. coli. The impact of the various alkoxy groups on antimicrobial activity was demonstrated. The crucial role of the substituents, located at the aromatic rings in the phenylethyloxy and benzyloxy groups, on the inhibitory action against selected pathogenic E. coli strains was revealed. The observed results are especially important because of increasing resistance of bacteria to various drugs and antibiotics.