title: Synthesis, characterization, and antibacterial activity of structurally complex 2-acylated 2,3,1-benzodiazaborines and related compounds.
abstract: A set of 2-acylated 2,3,1-benzodiazaborines and some related boron heterocycles were synthesized, characterized, and tested for antibacterial activity against Escherichia coli and Mycobacterium smegmatis. By high-field solution NMR, the heretofore unknown class of 2-acyl-1-hydroxy-2,3,1-diazaborines has been found to be able to exist in several interconvertable structural forms along a continuum comprised of an open hydrazone a, a monomeric B-hydroxy diazaborine b, and an anhydro dimer c. X-Ray crystallography of one of the anhydro dimers, 17c, revealed it to have an unprecedented structure featuring a double intramolecular O→B chelation. The crystal structure of another compound, 37, showed it to be based on a new pentacyclic B heterocycle framework. Nine compounds were found to possess activities against E. coli, and two others were active against M. smegmatis. The finding that these two contain isoniazid covalently embedded in their structures suggests that they might possibly be acting as prodrugs of this well-known antituberculosis agent in vivo.
authors.affiliation: Department of Chemistry and Biochemistry, California State University, East Bay, 25800 Carlos Bee Blvd., Hayward, CA 94542-3089, USA, (phone: +1-510-8853407; fax: +1-510-8854675).
authors.forename: Divya
authors.initials: D
authors.lastname: Kanichar
authors.forename: Lance
authors.initials: L
authors.lastname: Roppiyakuda
authors.forename: Ewa
authors.initials: E
authors.lastname: Kosmowska
authors.forename: Michelle A
authors.initials: MA
authors.lastname: Faust
authors.forename: Kim P
authors.initials: KP
authors.lastname: Tran
authors.forename: Felicia
authors.initials: F
authors.lastname: Chow
authors.forename: Elena
authors.initials: E
authors.lastname: Buglo
authors.forename: Michael P
authors.initials: MP
authors.lastname: Groziak
authors.forename: Evan A
authors.initials: EA
authors.lastname: Sarina
authors.forename: Marilyn M
authors.initials: MM
authors.lastname: Olmstead
authors.forename: Isba
authors.initials: I
authors.lastname: Silva
authors.forename: H Howard
authors.initials: HH
authors.lastname: Xu
mesh_terms: D000215:Acylation; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004926:Escherichia coli / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D020102:Mycobacterium smegmatis / Q000187:drug effects; D066244:Proton Magnetic Resonance Spectroscopy; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000900:Anti-Bacterial Agents; D001896:Boron Compounds
keywords: Antibacterial activity; Boron heterocycles; Isoniazid; Tuberculosis