biostudies-literatureUnknown32(1)Lapa GBClarithromycin (active against Gram positive infections) and 1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole derivatives (effective for Gram negative microbes) are the ligands of bacterial RNA. The antimicrobial activities of these benzoxaboroles linked with clarithromycin at 9 or 4″ position were compared. Two synthetic pathways for these conjugates were elaborated. First pathway explored the substitution of the C-9 carbonyl group of macrolactone's cycle via oxime linker, the second direction used the modification of the 4″-O-group of cladinose via the formation of carbamates of benzoxaboroles. 4″-O-(3-S-(1-Hydroxy-1,3-dihydro-benzo[c][1,2]oxaborole)-methyl-carbamoyl-clarithromycin showed twofold decrease in MICs for S. epidermidis and S. pneumoniae than clarithromycin. 4″-O-Modified clarithrJournal of enzyme inhibition and medicinal chemistry452-456https://www.ebi.ac.uk/biostudies/studies/S-EPMC6009856biostudies-literatureTwo approaches to the use of benzo[c][1,2]oxaboroles as active fragments for synthetic transformation of clarithromycin.PMC6009856Lapa GBIsakova EBMirchink EPPreobrazhenskaya MNfalseTwo approaches to the use of benzo[c][1,2]oxaboroles as active fragments for synthetic transformation of clarithromycin.Clarithromycin (active against Gram positive infections) and 1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole derivatives (effective for Gram negative microbes) are the ligands of bacterial RNA. The antimicrobial activities of these benzoxaboroles linked with clarithromycin at 9 or 4″ position were compared. Two synthetic pathways for these conjugates were elaborated. First pathway explored the substitution of the C-9 carbonyl group of macrolactone's cycle via oxime linker, the second direction used the modification of the 4″-O-group of cladinose via the formation of carbamates of benzoxaboroles. 4″-O-(3-S-(1-Hydroxy-1,3-dihydro-benzo[c][1,2]oxaborole)-methyl-carbamoyl-clarithromycin showed twofold decrease in MICs for S. epidermidis and S. pneumoniae than clarithromycin. 4″-O-Modified clarithr2017-01-01T00:00:00Z2017 Dec2025-04-22T12:48:52.797Z2019-03-26T23:45:43ZS-EPMC60098562809789810.1080/14756366.2016.1261129