5-Benzylidenerhodanine and 5-benzylidene-2-4-thiazolidinedione based antibacterials

Ondrej Zvarec; Steven W. Polyak; William Tieu; Kevin Kuan; Huanqin Dai; Daniel Sejer Pedersen; Renato Morona; Lixin Zhang; Grant W. Booker; Andrew D. Abell

doi:10.1016/j.bmcl.2012.02.100

5-Benzylidenerhodanine and 5-benzylidene-2-4-thiazolidinedione based antibacterials

Ondrej Zvarec, Steven W. Polyak, William Tieu, Kevin Kuan, Huanqin Dai, Daniel Sejer Pedersen, Renato Morona, Lixin Zhang, Grant W. Booker, Andrew D. Abell

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

42 Citations (Scopus)

Abstract

Herein we outline the antibacterial activity of amino acid containing thiazolidinediones and rhodanines against Gram-positive bacteria Staphylococcus aureus ATCC 31890, Staphylococcus epidermidis and Bacillus subtilis ATCC 6633. The rhodanine derivatives were generally more active than the analogous thiazolidinediones. Compounds of series 5 showed some selectivity for Bacillus subtilis ATCC 6633, the extent of which is enhanced by the inclusion of a non-polar amino acid at the 5-position of the core thiazolidinediones and rhodanines scaffolds. SAR data of series 8 demonstrated improved activity against the clinically more significant Staphylococci with selectivity over Bacillus subtilis ATCC 6633 induced by introduction of a bulky aryl substituent at the 5-position of the core scaffolds.

Original language	English
Pages (from-to)	2720-2722
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	22
Issue number	8
DOIs	https://doi.org/10.1016/j.bmcl.2012.02.100
Publication status	Published or Issued - 15 Apr 2012
Externally published	Yes

Keywords

Antibacterial
Privileged scaffold
Rhodanines
Staphylococcus aureus
Thiazolidinedione

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2012.02.100

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title = "5-Benzylidenerhodanine and 5-benzylidene-2-4-thiazolidinedione based antibacterials",

abstract = "Herein we outline the antibacterial activity of amino acid containing thiazolidinediones and rhodanines against Gram-positive bacteria Staphylococcus aureus ATCC 31890, Staphylococcus epidermidis and Bacillus subtilis ATCC 6633. The rhodanine derivatives were generally more active than the analogous thiazolidinediones. Compounds of series 5 showed some selectivity for Bacillus subtilis ATCC 6633, the extent of which is enhanced by the inclusion of a non-polar amino acid at the 5-position of the core thiazolidinediones and rhodanines scaffolds. SAR data of series 8 demonstrated improved activity against the clinically more significant Staphylococci with selectivity over Bacillus subtilis ATCC 6633 induced by introduction of a bulky aryl substituent at the 5-position of the core scaffolds.",

keywords = "Antibacterial, Privileged scaffold, Rhodanines, Staphylococcus aureus, Thiazolidinedione",

author = "Ondrej Zvarec and Polyak, \{Steven W.\} and William Tieu and Kevin Kuan and Huanqin Dai and Pedersen, \{Daniel Sejer\} and Renato Morona and Lixin Zhang and Booker, \{Grant W.\} and Abell, \{Andrew D.\}",

year = "2012",

month = apr,

day = "15",

doi = "10.1016/j.bmcl.2012.02.100",

language = "English",

volume = "22",

pages = "2720--2722",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Ltd",

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TY - JOUR

T1 - 5-Benzylidenerhodanine and 5-benzylidene-2-4-thiazolidinedione based antibacterials

AU - Zvarec, Ondrej

AU - Polyak, Steven W.

AU - Tieu, William

AU - Kuan, Kevin

AU - Dai, Huanqin

AU - Pedersen, Daniel Sejer

AU - Morona, Renato

AU - Zhang, Lixin

AU - Booker, Grant W.

AU - Abell, Andrew D.

PY - 2012/4/15

Y1 - 2012/4/15

N2 - Herein we outline the antibacterial activity of amino acid containing thiazolidinediones and rhodanines against Gram-positive bacteria Staphylococcus aureus ATCC 31890, Staphylococcus epidermidis and Bacillus subtilis ATCC 6633. The rhodanine derivatives were generally more active than the analogous thiazolidinediones. Compounds of series 5 showed some selectivity for Bacillus subtilis ATCC 6633, the extent of which is enhanced by the inclusion of a non-polar amino acid at the 5-position of the core thiazolidinediones and rhodanines scaffolds. SAR data of series 8 demonstrated improved activity against the clinically more significant Staphylococci with selectivity over Bacillus subtilis ATCC 6633 induced by introduction of a bulky aryl substituent at the 5-position of the core scaffolds.

AB - Herein we outline the antibacterial activity of amino acid containing thiazolidinediones and rhodanines against Gram-positive bacteria Staphylococcus aureus ATCC 31890, Staphylococcus epidermidis and Bacillus subtilis ATCC 6633. The rhodanine derivatives were generally more active than the analogous thiazolidinediones. Compounds of series 5 showed some selectivity for Bacillus subtilis ATCC 6633, the extent of which is enhanced by the inclusion of a non-polar amino acid at the 5-position of the core thiazolidinediones and rhodanines scaffolds. SAR data of series 8 demonstrated improved activity against the clinically more significant Staphylococci with selectivity over Bacillus subtilis ATCC 6633 induced by introduction of a bulky aryl substituent at the 5-position of the core scaffolds.

KW - Antibacterial

KW - Privileged scaffold

KW - Rhodanines

KW - Staphylococcus aureus

KW - Thiazolidinedione

UR - https://www.scopus.com/pages/publications/84862807215

U2 - 10.1016/j.bmcl.2012.02.100

DO - 10.1016/j.bmcl.2012.02.100

M3 - Article

C2 - 22444680

AN - SCOPUS:84862807215

SN - 0960-894X

VL - 22

SP - 2720

EP - 2722

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 8

ER -

5-Benzylidenerhodanine and 5-benzylidene-2-4-thiazolidinedione based antibacterials

Abstract

Keywords

ASJC Scopus subject areas

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