4-Alkyl and 4,4′-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5- dione derivatives as new inhibitors of bacterial cell wall biosynthesis

Kristina M.K. Kutterer; Jamie M. Davis; Guy Singh; Youjun Yang; William Hu; Anatoly Severin; Beth A. Rasmussen; Girija Krishnamurthy; Amedeo Failli; Alan H. Katz

doi:10.1016/j.bmcl.2005.03.058

4-Alkyl and 4,4′-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5- dione derivatives as new inhibitors of bacterial cell wall biosynthesis

Kristina M.K. Kutterer
, Jamie M. Davis
, Guy Singh
, Youjun Yang
, William Hu
, Anatoly Severin
, Beth A. Rasmussen
, Girija Krishnamurthy
, Amedeo Failli
, Alan H. Katz

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

61 Scopus citations

Abstract

Over 195 4-alkyl and 4,4-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5- dione derivatives were synthesized, utilizing microwave accelerated synthesis, for evaluation as new inhibitors of bacterial cell wall biosynthesis. Many of them demonstrated good activity against MurB in vitro and low MIC values against Gram-positive bacteria, particularly penicillin-resistant Streptococcus pneumoniae (PRSP). Derivative 7l demonstrated antibacterial activity against both Gram-positive and Gram-negative bacteria. Derivatives 7f and 10a also demonstrated potent nanomolar K_d values in their binding to MurB.

Original language	English
Pages (from-to)	2527-2531
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	15
Issue number	10
DOIs	https://doi.org/10.1016/j.bmcl.2005.03.058
State	Published - May 16 2005
Externally published	Yes

Keywords

Antibacterial activity
Microwave-assisted synthesis
MurA
MurB
Pyrazolidinediones

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10.1016/j.bmcl.2005.03.058

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Kutterer, K. M. K., Davis, J. M., Singh, G., Yang, Y., Hu, W., Severin, A., Rasmussen, B. A., Krishnamurthy, G., Failli, A., & Katz, A. H. (2005). 4-Alkyl and 4,4′-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5- dione derivatives as new inhibitors of bacterial cell wall biosynthesis. Bioorganic and Medicinal Chemistry Letters, 15(10), 2527-2531. https://doi.org/10.1016/j.bmcl.2005.03.058

@article{367b6f82151a4103a3ca04d7760fb840,

title = "4-Alkyl and 4,4′-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5- dione derivatives as new inhibitors of bacterial cell wall biosynthesis",

abstract = "Over 195 4-alkyl and 4,4-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5- dione derivatives were synthesized, utilizing microwave accelerated synthesis, for evaluation as new inhibitors of bacterial cell wall biosynthesis. Many of them demonstrated good activity against MurB in vitro and low MIC values against Gram-positive bacteria, particularly penicillin-resistant Streptococcus pneumoniae (PRSP). Derivative 7l demonstrated antibacterial activity against both Gram-positive and Gram-negative bacteria. Derivatives 7f and 10a also demonstrated potent nanomolar Kd values in their binding to MurB.",

keywords = "Antibacterial activity, Microwave-assisted synthesis, MurA, MurB, Pyrazolidinediones",

author = "Kutterer, \{Kristina M.K.\} and Davis, \{Jamie M.\} and Guy Singh and Youjun Yang and William Hu and Anatoly Severin and Rasmussen, \{Beth A.\} and Girija Krishnamurthy and Amedeo Failli and Katz, \{Alan H.\}",

year = "2005",

month = may,

day = "16",

doi = "10.1016/j.bmcl.2005.03.058",

language = "English",

volume = "15",

pages = "2527--2531",

journal = "Bioorganic and Medicinal Chemistry Letters",

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number = "10",

}

Kutterer, KMK, Davis, JM, Singh, G, Yang, Y, Hu, W, Severin, A, Rasmussen, BA, Krishnamurthy, G, Failli, A & Katz, AH 2005, '4-Alkyl and 4,4′-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5- dione derivatives as new inhibitors of bacterial cell wall biosynthesis', Bioorganic and Medicinal Chemistry Letters, vol. 15, no. 10, pp. 2527-2531. https://doi.org/10.1016/j.bmcl.2005.03.058

TY - JOUR

T1 - 4-Alkyl and 4,4′-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5- dione derivatives as new inhibitors of bacterial cell wall biosynthesis

AU - Kutterer, Kristina M.K.

AU - Davis, Jamie M.

AU - Singh, Guy

AU - Yang, Youjun

AU - Hu, William

AU - Severin, Anatoly

AU - Rasmussen, Beth A.

AU - Krishnamurthy, Girija

AU - Failli, Amedeo

AU - Katz, Alan H.

PY - 2005/5/16

Y1 - 2005/5/16

N2 - Over 195 4-alkyl and 4,4-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5- dione derivatives were synthesized, utilizing microwave accelerated synthesis, for evaluation as new inhibitors of bacterial cell wall biosynthesis. Many of them demonstrated good activity against MurB in vitro and low MIC values against Gram-positive bacteria, particularly penicillin-resistant Streptococcus pneumoniae (PRSP). Derivative 7l demonstrated antibacterial activity against both Gram-positive and Gram-negative bacteria. Derivatives 7f and 10a also demonstrated potent nanomolar Kd values in their binding to MurB.

AB - Over 195 4-alkyl and 4,4-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5- dione derivatives were synthesized, utilizing microwave accelerated synthesis, for evaluation as new inhibitors of bacterial cell wall biosynthesis. Many of them demonstrated good activity against MurB in vitro and low MIC values against Gram-positive bacteria, particularly penicillin-resistant Streptococcus pneumoniae (PRSP). Derivative 7l demonstrated antibacterial activity against both Gram-positive and Gram-negative bacteria. Derivatives 7f and 10a also demonstrated potent nanomolar Kd values in their binding to MurB.

KW - Antibacterial activity

KW - Microwave-assisted synthesis

KW - MurA

KW - MurB

KW - Pyrazolidinediones

UR - https://www.scopus.com/pages/publications/20944432485

U2 - 10.1016/j.bmcl.2005.03.058

DO - 10.1016/j.bmcl.2005.03.058

M3 - Article

C2 - 15863310

AN - SCOPUS:20944432485

SN - 0960-894X

VL - 15

SP - 2527

EP - 2531

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 10

ER -

4-Alkyl and 4,4′-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5- dione derivatives as new inhibitors of bacterial cell wall biosynthesis

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Keywords

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