Issue 10, 2003
From the journal:

New Journal of Chemistry

Synthesis and antifungal and antibacterial bioactivity of cyclic diamines containing boronate esters

Alison M. Irving,a   Christopher M. Vogels,a   Liliya G. Nikolcheva,a   Janet P. Edwards,a   Xiao-Feng He,a   Michael G. Hamilton,a   Mark O. Baerlocher,b   Felix J. Baerlocher,b   Andreas Deckenc  and  Stephen A. Westcott*a  

* Corresponding authors

a Department of Chemistry, Mount Allison University, Sackville, Canada

b Department of Biology, Mount Allison University, Sackville, Canada

c Department of Chemistry, University of New Brunswick, Fredericton, Canada

Abstract

Novel N2B heterocycles (1–5) are formed from the reaction of ethylenediamine derivatives with 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (2-HC(O)C6H4Bpin; pin = 1,2-O2C2Me4). X-ray diffraction studies have been carried out on four examples and show that reactions are selective in giving the isomer where the least substituted amine coordinates to the Lewis-acidic boron atom. Reaction of 2-HC(O)C6H4Bpin with diethylenetriamine gave a heterocycle (6) with a pendant primary amine group, which reacts further with 2-pyridinecarboxaldehyde to give a potential ligand (7) for transition metals. All new compounds show considerable antifungal activity against Aspergillus niger and Aspergillus flavus and moderate antibacterial activity against Bacillus cereus.

Graphical abstract: Synthesis and antifungal and antibacterial bioactivity of cyclic diamines containing boronate esters

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Article information

DOI
https://doi.org/10.1039/B304500E
Article type
Paper
Submitted
23 Apr 2003
Accepted
09 Jun 2003
First published
21 Aug 2003

New J. Chem., 2003,27, 1419-1424

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Synthesis and antifungal and antibacterial bioactivity of cyclic diamines containing boronate esters

A. M. Irving, C. M. Vogels, L. G. Nikolcheva, J. P. Edwards, X. He, M. G. Hamilton, M. O. Baerlocher, F. J. Baerlocher, A. Decken and S. A. Westcott, New J. Chem., 2003, 27, 1419 DOI: 10.1039/B304500E

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