Literature DB >> 18295483

Design and structure-activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): tetramic, tetronic acids and dihydropyridin-2-ones.

Stefan Peukert1, Yingchuan Sun, Rui Zhang, Brian Hurley, Mike Sabio, Xiaoyu Shen, Christen Gray, JoAnn Dzink-Fox, Jianshi Tao, Regina Cebula, Sompong Wattanasin.   

Abstract

Based on a pharmacophore hypothesis substituted tetramic and tetronic acid 3-carboxamides as well as dihydropyridin-2-one-3-carboxamides were investigated as inhibitors of undecaprenyl pyrophosphate synthase (UPPS) for use as novel antimicrobial agents. Synthesis and structure-activity relationship patterns for this class of compounds are discussed. Selectivity data and antibacterial activities for selected compounds are provided.

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Year:  2008        PMID： 18295483     DOI： 10.1016/j.bmcl.2008.02.009

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  32 in total

1.  HIV-1 Integrase Inhibitor-Inspired Antibacterials Targeting Isoprenoid Biosynthesis.

Authors:  Yonghui Zhang; Kai Li; Wei Zhu; Yi-Liang Liu; Rong Cao; Ran Pang; Eunhae Lee; Jordan Axelson; Mary Hensler; Ke Wang; Katie J Molohon; Yang Wang; Douglas A Mitchell; Victor Nizet; Eric Oldfield
Journal:  ACS Med Chem Lett       Date:  2012-04-03       Impact factor: 4.345

2.  Indolizinones as synthetic scaffolds: fundamental reactivity and the relay of stereochemical information.

Authors:  Alison R Hardin Narayan; Richmond Sarpong
Journal:  Org Biomol Chem       Date:  2011-11-09       Impact factor: 3.876

Review 3.  Challenges of antibacterial discovery.

Authors:  Lynn L Silver
Journal:  Clin Microbiol Rev       Date:  2011-01       Impact factor: 26.132

4.  Bacterial Cell Growth Inhibitors Targeting Undecaprenyl Diphosphate Synthase and Undecaprenyl Diphosphate Phosphatase.

Authors:  Yang Wang; Janish Desai; Yonghui Zhang; Satish R Malwal; Christopher J Shin; Xinxin Feng; Hong Sun; Guizhi Liu; Rey-Ting Guo; Eric Oldfield
Journal:  ChemMedChem       Date:  2016-08-31       Impact factor: 3.466

5.  Antibacterial drug leads targeting isoprenoid biosynthesis.

Authors:  Wei Zhu; Yonghui Zhang; William Sinko; Mary E Hensler; Joshua Olson; Katie J Molohon; Steffen Lindert; Rong Cao; Kai Li; Ke Wang; Yang Wang; Yi-Liang Liu; Anna Sankovsky; César Augusto F de Oliveira; Douglas A Mitchell; Victor Nizet; J Andrew McCammon; Eric Oldfield
Journal:  Proc Natl Acad Sci U S A       Date:  2012-12-17       Impact factor: 11.205

6.  Gastrointestinal localization of metronidazole by a lactobacilli-inspired tetramic acid motif improves treatment outcomes in the hamster model of Clostridium difficile infection.

Authors:  Philip T Cherian; Xiaoqian Wu; Lei Yang; Jerrod S Scarborough; Aman P Singh; Zahidul A Alam; Richard E Lee; Julian G Hurdle
Journal:  J Antimicrob Chemother       Date:  2015-08-18       Impact factor: 5.790

7.  Bisphosphonate inhibition of a Plasmodium farnesyl diphosphate synthase and a general method for predicting cell-based activity from enzyme data.

Authors:  Dushyant Mukkamala; Joo Hwan No; Lauren M Cass; Ting-Kai Chang; Eric Oldfield
Journal:  J Med Chem       Date:  2008-12-25       Impact factor: 7.446

8.  Biophysical investigation of the mode of inhibition of tetramic acids, the allosteric inhibitors of undecaprenyl pyrophosphate synthase.

Authors:  Lac V Lee; Brian Granda; Karl Dean; Jianshi Tao; Eugene Liu; Rui Zhang; Stefan Peukert; Sompong Wattanasin; Xiaoling Xie; Neil S Ryder; Ruben Tommasi; Gejing Deng
Journal:  Biochemistry       Date:  2010-06-29       Impact factor: 3.162

9.  Identifying essential genes in bacterial metabolic networks with machine learning methods.

Authors:  Kitiporn Plaimas; Roland Eils; Rainer König
Journal:  BMC Syst Biol       Date:  2010-05-03

10.  Synthesis and Crystal Structure Characterization of Zinc (II) Tetronic Acid Complexes.

Authors:  K C Prousis; G Athanasellis; V Stefanou; D Matiadis; E Kokalari; O Igglessi-Markopoulou; V McKee; J Markopoulos
Journal:  Bioinorg Chem Appl       Date:  2010-11-04       Impact factor: 7.778
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