Literature DB >> 3082839

Semisynthetic beta-lactam antibiotics. I. Synthesis and antibacterial activity of new ureidopenicillin derivatives having catechol moieties.

N Ohi, B Aoki, T Shinozaki, K Moro, T Noto, T Nehashi, H Okazaki, I Matsunaga.   

Abstract

The synthesis and antibacterial activity of new ureidopenicillin derivatives having catechol moieties in the 6-acyl side chain are described. These compounds showed remarkably strong activities against Pseudomonas aeruginosa. Especially, 6-[(R)-2-[3-(3,4-dihydroxybenzoyl)-3-methyl-1-ureido]-2- phenylacetamido]penicillanic acid (7a) had the most potent activity in vitro against Gram-negative bacteria, its activity being 30 approximately 60-fold greater than that of piperacillin against most strains of P. aeruginosa.

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Year:  1986        PMID： 3082839     DOI： 10.7164/antibiotics.39.230

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN： 0021-8820            Impact factor:   2.649


  14 in total

1.  In vitro antibacterial activity of KP-736, a new cephem antibiotic.

Authors:  T Maejima; M Inoue; S Mitsuhashi
Journal:  Antimicrob Agents Chemother       Date:  1991-01       Impact factor: 5.191

2.  In vitro activity of a catechol-substituted cephalosporin, GR69153.

Authors:  R Wise; J M Andrews; J P Ashby; D Thornber
Journal:  Antimicrob Agents Chemother       Date:  1991-02       Impact factor: 5.191

3.  Evaluation of growth promotion and inhibition from mycobactins and nonmycobacterial siderophores (Desferrioxamine and FR160) in Mycobacterium aurum.

Authors:  S Bosne-David; L Bricard; F Ramiandrasoa; A DeRoussent; G Kunesch; A Andremont
Journal:  Antimicrob Agents Chemother       Date:  1997-08       Impact factor: 5.191

4.  Iron-regulated outer membrane proteins of Escherichia coli K-12 and mechanism of action of catechol-substituted cephalosporins.

Authors:  N A Curtis; R L Eisenstadt; S J East; R J Cornford; L A Walker; A J White
Journal:  Antimicrob Agents Chemother       Date:  1988-12       Impact factor: 5.191

5.  Cir and Fiu proteins in the outer membrane of Escherichia coli catalyze transport of monomeric catechols: study with beta-lactam antibiotics containing catechol and analogous groups.

Authors:  H Nikaido; E Y Rosenberg
Journal:  J Bacteriol       Date:  1990-03       Impact factor: 3.490

6.  Preparation, gram-negative antibacterial activity, and hydrolytic stability of novel siderophore-conjugated monocarbam diols.

Authors:  Mark E Flanagan; Steven J Brickner; Manjinder Lall; Jeffrey Casavant; Laura Deschenes; Steven M Finegan; David M George; Karl Granskog; Joel R Hardink; Michael D Huband; Thuy Hoang; Lucinda Lamb; Andrea Marra; Mark Mitton-Fry; John P Mueller; Lisa M Mullins; Mark C Noe; John P O'Donnell; David Pattavina; Joseph B Penzien; Brandon P Schuff; Jianmin Sun; David A Whipple; Jennifer Young; Thomas D Gootz
Journal:  ACS Med Chem Lett       Date:  2011-03-02       Impact factor: 4.345

7.  Iron transport-mediated antibacterial activity of and development of resistance to hydroxamate and catechol siderophore-carbacephalosporin conjugates.

Authors:  A A Minnick; J A McKee; E K Dolence; M J Miller
Journal:  Antimicrob Agents Chemother       Date:  1992-04       Impact factor: 5.191

8.  Modes of action and inhibitory activities of new siderophore-beta-lactam conjugates that use specific iron uptake pathways for entry into bacteria.

Authors:  A Brochu; N Brochu; T I Nicas; T R Parr; A A Minnick; E K Dolence; J A McKee; M J Miller; M C Lavoie; F Malouin
Journal:  Antimicrob Agents Chemother       Date:  1992-10       Impact factor: 5.191

9.  Enterobactin-mediated delivery of β-lactam antibiotics enhances antibacterial activity against pathogenic Escherichia coli.

Authors:  Tengfei Zheng; Elizabeth M Nolan
Journal:  J Am Chem Soc       Date:  2014-06-27       Impact factor: 15.419

Review 10.  Iron Acquisition Systems of Gram-negative Bacterial Pathogens Define TonB-Dependent Pathways to Novel Antibiotics.

Authors:  Phillip E Klebba; Salete M C Newton; David A Six; Ashish Kumar; Taihao Yang; Brittany L Nairn; Colton Munger; Somnath Chakravorty
Journal:  Chem Rev       Date:  2021-03-16       Impact factor: 60.622
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