Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development

Xin Liu; Paul Carr; Michael G. Gardiner; Martin G. Banwell; Martin G. Banwell; Ahmed H. Elbanna; Zeinab G. Khalil; Robert J. Capon

doi:10.1021/acsomega.0c01331

Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development

Xin Liu, Paul Carr, Michael G. Gardiner, Martin G. Banwell^*, Martin G. Banwell^*, Ahmed H. Elbanna, Zeinab G. Khalil, Robert J. Capon

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

The bioderived platform molecule levoglucosenone (LGO, 1) and its readily prepared pseudoenantiomer (iso-LGO, 2) have each been subjected to α-iodination reactions with the product halides then being engaged in palladium-catalyzed Ullmann cross-coupling reactions with various bromonitropyridines. The corresponding α-pyridinylated derivatives such as 11 and 24, respectively, are produced as a result. Biological screening of such products reveals that certain of them display potent and selective antimicrobial and/or cytotoxic properties. In contrast, the azaindoles obtained by reductive cyclization of compounds such as 11 and 12 are essentially inactive in these respects. Preliminary mode-of-action studies are reported.

Original language	English
Pages (from-to)	13926-13939
Number of pages	14
Journal	ACS Omega
Volume	5
Issue number	23
DOIs	https://doi.org/10.1021/acsomega.0c01331
Publication status	Published - 16 Jun 2020

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title = "Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development",

abstract = "The bioderived platform molecule levoglucosenone (LGO, 1) and its readily prepared pseudoenantiomer (iso-LGO, 2) have each been subjected to α-iodination reactions with the product halides then being engaged in palladium-catalyzed Ullmann cross-coupling reactions with various bromonitropyridines. The corresponding α-pyridinylated derivatives such as 11 and 24, respectively, are produced as a result. Biological screening of such products reveals that certain of them display potent and selective antimicrobial and/or cytotoxic properties. In contrast, the azaindoles obtained by reductive cyclization of compounds such as 11 and 12 are essentially inactive in these respects. Preliminary mode-of-action studies are reported.",

author = "Xin Liu and Paul Carr and Gardiner, \{Michael G.\} and Banwell, \{Martin G.\} and Banwell, \{Martin G.\} and Elbanna, \{Ahmed H.\} and Khalil, \{Zeinab G.\} and Capon, \{Robert J.\}",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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day = "16",

doi = "10.1021/acsomega.0c01331",

language = "English",

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T1 - Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development

AU - Liu, Xin

AU - Carr, Paul

AU - Gardiner, Michael G.

AU - Banwell, Martin G.

AU - Elbanna, Ahmed H.

AU - Khalil, Zeinab G.

AU - Capon, Robert J.

PY - 2020/6/16

Y1 - 2020/6/16

N2 - The bioderived platform molecule levoglucosenone (LGO, 1) and its readily prepared pseudoenantiomer (iso-LGO, 2) have each been subjected to α-iodination reactions with the product halides then being engaged in palladium-catalyzed Ullmann cross-coupling reactions with various bromonitropyridines. The corresponding α-pyridinylated derivatives such as 11 and 24, respectively, are produced as a result. Biological screening of such products reveals that certain of them display potent and selective antimicrobial and/or cytotoxic properties. In contrast, the azaindoles obtained by reductive cyclization of compounds such as 11 and 12 are essentially inactive in these respects. Preliminary mode-of-action studies are reported.

AB - The bioderived platform molecule levoglucosenone (LGO, 1) and its readily prepared pseudoenantiomer (iso-LGO, 2) have each been subjected to α-iodination reactions with the product halides then being engaged in palladium-catalyzed Ullmann cross-coupling reactions with various bromonitropyridines. The corresponding α-pyridinylated derivatives such as 11 and 24, respectively, are produced as a result. Biological screening of such products reveals that certain of them display potent and selective antimicrobial and/or cytotoxic properties. In contrast, the azaindoles obtained by reductive cyclization of compounds such as 11 and 12 are essentially inactive in these respects. Preliminary mode-of-action studies are reported.

UR - https://www.scopus.com/pages/publications/85087468387

U2 - 10.1021/acsomega.0c01331

DO - 10.1021/acsomega.0c01331

M3 - Article

SN - 2470-1343

VL - 5

SP - 13926

EP - 13939

JO - ACS Omega

JF - ACS Omega

IS - 23

ER -

Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development

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