Tam Minh Le1,2, Thu Huynh3,4,5, Fatima Zahra Bamou1, András Szekeres3,6, Ferenc Fülöp1,2, Zsolt Szakonyi1,6. 1. Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary Excellent Center, Eötvös utca 6, H-6720 Szeged, Hungary. 2. Stereochemistry Research Group of the Hungarian Academy of Sciences, Eötvös utca 6, H-6720 Szeged, Hungary. 3. Department of Microbiology, University of Szeged, Közép fasor 52, 6726 Szeged, Hungary. 4. Department of Biotecnology, Faculty of Chemical Engineering, Ho Chi Minh University of Technology (HCMUT), 268 Ly Thuong Kiet Street, District 10, Ho Chi Minh City 72607, Vietnam. 5. Vietnam National University Ho Chi Minh City, Linh Trung Ward, Thu Duc District, Ho Chi Minh City 71351, Vietnam. 6. Interdisciplinary Centre of Natural Products, University of Szeged, Eötvös utca 6, H-6720 Szeged, Hungary.
Abstract
Discovery of novel antibacterial agents with new structures, which combat pathogens is an urgent task. In this study, a new library of (+)-neoisopulegol-based O-benzyl derivatives of aminodiols and aminotriols was designed and synthesized, and their antimicrobial activity against different bacterial and fungal strains were evaluated. The results showed that this new series of synthetic O-benzyl compounds exhibit potent antimicrobial activity. Di-O-benzyl derivatives showed high activity against Gram-positive bacteria and fungi, but moderate activity against Gram-negative bacteria. Therefore, these compounds may serve a good basis for antibacterial and antifungal drug discovery. Structure-activity relationships were also studied from the aspects of stereochemistry of the O-benzyl group on cyclohexane ring and the substituent effects on the ring system.
Discovery of novel antibacterial agents with new structures, which combat pathogens is an urgent task. In this study, a new library of (+)-neoisopulegol-based n class="Chemical">O-benzyl derivatives of aminodiols and aminotriols was designed and synthesized, and their antimicrobial activity against different bacterial and fungal strains were evaluated. The results showed that this new series of synthetic O-benzyl compounds exhibit potent antimicrobial activity. Di-O-benzyl derivatives showed high activity against Gram-positive bacteria and fungi, but moderate activity against Gram-negative bacteria. Therefore, these compounds may serve a good basis for antibacterial and antifungal drug discovery. Structure-activity relationships were also studied from the aspects of stereochemistry of the O-benzyl group on cyclohexane ring and the substituent effects on the ring system.
Authors: Lotta Glans; Andreas Ehnbom; Carmen de Kock; Alberto Martínez; Jesús Estrada; Peter J Smith; Matti Haukka; Roberto A Sánchez-Delgado; Ebbe Nordlander Journal: Dalton Trans Date: 2012-01-17 Impact factor: 4.390