Synthesis, Characterization, and Antibacterial Activity of Structurally Complex 2‐Acylated 2, 3, 1‐Benzodiazaborines and Related Compounds. Issue 9 (September 2014)

• Record Type: Journal Article
• Authors: Kanichar, Divya; Roppiyakuda, Lance; Kosmowska, Ewa; Faust, Michelle A.; Tran, Kim P.; Chow, Felicia; Buglo, Elena; Groziak, Michael P.; Sarina, Evan A.; Olmstead, Marilyn M.; Silva, Isba; Xu, H. Howard
• Is Part Of: Chemistry & biodiversity. Volume 11:Issue 9(2014:Sep.)
• Page Start: 1381
• Page End: 1397
• Publication Date: 2014-09
• Subjects: Biochemistry -- Periodicals; Molecular biology -- Periodicals; Biodiversity -- Periodicals; 572
• DOI: 10.1002/cbdv.201400007
• Languages: English
• ISSNs: 1612-1872

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A set of 2‐acylated 2, 3, 1‐benzodiazaborines and some related boron heterocycles were synthesized, characterized, and tested for antibacterial activity against <italic>Escherichia coli</italic> and <italic>Mycobacterium smegmatis.</italic> 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 <bold>a</bold>, a monomeric <italic>B</italic>‐hydroxy diazaborine <bold>b</bold>, and an anhydro dimer <bold>c</bold>. X‐Ray crystallography of one of the anhydro dimers, <bold>17c</bold>, revealed it to have an unprecedented structure featuring a double intramolecular O→B chelation. The crystal structure of another compound, <bold>37</bold>, showed it to be based on a new pentacyclic B heterocycle framework. Nine compounds were found to possess activities against <italic>E. coli</italic>, and two others were active against <italic>M. smegmatis.</italic> 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 <italic>in vivo.</italic></p> </abstract>