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

被引：61

作者：

Irving, AM

Vogels, CM

Nikolcheva, LG

Edwards, JP

He, XF

Hamilton, MG

Baerlocher, MO

Baerlocher, FJ

Decken, A

Westcott, SA ^{[1
]}

机构：

[1] Mt Allison Univ, Dept Chem, Sackville, NB E4L 1G8, Canada

[2] Mt Allison Univ, Dept Biol, Sackville, NB E4L 1G8, Canada

[3] Univ New Brunswick, Dept Chem, Fredericton, NB E3B 5A3, Canada

来源：

NEW JOURNAL OF CHEMISTRY | 2003年 / 27卷 / 10期

关键词：

D O I：

10.1039/b304500e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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)C(6)H(4)Bpin; 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)C(6)H(4)Bpin 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.

引用

页码：1419 / 1424

页数：6

共 65 条

[21] Synthesis of boronic acid analogues of α-amino acids by introducing side chains as electrophiles [J].