Literature DB >> 17188860

Synthesis and SAR of 3,5-diamino-piperidine derivatives: novel antibacterial translation inhibitors as aminoglycoside mimetics.

Yuefen Zhou1, Vlad E Gregor, Benjamin K Ayida, Geoffrey C Winters, Zhongxiang Sun, Douglas Murphy, Greg Haley, Dwight Bailey, Jamie M Froelich, Sarah Fish, Stephen E Webber, Thomas Hermann, Daniel Wall.   

Abstract

Aminoglycoside antibiotics target an internal RNA loop within the bacterial ribosomal decoding site. Here, we describe the synthesis and SAR of novel 3,5-diamino-piperidine derivatives as aminoglycoside mimetics, and show they act as inhibitors of bacterial translation and growth.

Entities:  

Mesh：

Substances：

Year:  2006        PMID： 17188860      PMCID： PMC1858661          DOI： 10.1016/j.bmcl.2006.12.024

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


  15 in total

1.  Functional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics.

Authors:  A P Carter; W M Clemons; D E Brodersen; R J Morgan-Warren; B T Wimberly; V Ramakrishnan
Journal:  Nature       Date:  2000-09-21       Impact factor: 49.962

2.  Piperidine glycosides targeting the ribosomal decoding site.

Authors:  Klaus B Simonsen; Benjamin K Ayida; Dionisios Vourloumis; Geoffrey C Winters; Masayuki Takahashi; Sarah Shandrick; Qiang Zhao; Thomas Hermann
Journal:  Chembiochem       Date:  2003-09-05       Impact factor: 3.164

3.  Novel acyclic deoxystreptamine mimetics targeting the ribosomal decoding site.

Authors:  Dionisios Vourloumis; Geoffrey C Winters; Masayuki Takahashi; Klaus B Simonsen; Benjamin K Ayida; Sarah Shandrick; Qiang Zhao; Thomas Hermann
Journal:  Chembiochem       Date:  2003-09-05       Impact factor: 3.164

4.  A structure-based strategy to identify new molecular scaffolds targeting the bacterial ribosomal A-site.

Authors:  Nicolas Foloppe; I-Jen Chen; Ben Davis; Adam Hold; Dave Morley; Rob Howes
Journal:  Bioorg Med Chem       Date:  2004-03-01       Impact factor: 3.641

Review 5.  2-Deoxystreptamine: central scaffold of aminoglycoside antibiotics.

Authors:  Guuske F Busscher; Floris P J T Rutjes; Floris L van Delft
Journal:  Chem Rev       Date:  2005-03       Impact factor: 60.622

6.  Molecular recognition by glycoside pseudo base pairs and triples in an apramycin-RNA complex.

Authors:  Qing Han; Qiang Zhao; Sarah Fish; Klaus B Simonsen; Dionisios Vourloumis; Jamie M Froelich; Daniel Wall; Thomas Hermann
Journal:  Angew Chem Int Ed Engl       Date:  2005-04-29       Impact factor: 15.336

7.  Structure-activity relationships of novel antibacterial translation inhibitors: 3,5-diamino-piperidinyl triazines.

Authors:  Yuefen Zhou; Zhongxiang Sun; Jamie M Froelich; Thomas Hermann; Daniel Wall
Journal:  Bioorg Med Chem Lett       Date:  2006-08-04       Impact factor: 2.823

Review 8.  Defining the need for new antimicrobials: clinical and economic implications of resistance in the hospitalised patient.

Authors:  C Andrew DeRyke; Dana Maglio; David P Nicolau
Journal:  Expert Opin Pharmacother       Date:  2005-06       Impact factor: 3.889

9.  Rational design of azepane-glycoside antibiotics targeting the bacterial ribosome.

Authors:  Sofia Barluenga; Klaus B Simonsen; Ethel S Littlefield; Benjamin K Ayida; Dionisios Vourloumis; Geoffrey C Winters; Masayuki Takahashi; Sarah Shandrick; Qiang Zhao; Qing Han; Thomas Hermann
Journal:  Bioorg Med Chem Lett       Date:  2004-02-09       Impact factor: 2.823

10.  The molecular basis for A-site mutations conferring aminoglycoside resistance: relationship between ribosomal susceptibility and X-ray crystal structures.

Authors:  Peter Pfister; Sven Hobbie; Quentin Vicens; Erik C Böttger; Eric Westhof
Journal:  Chembiochem       Date:  2003-10-06       Impact factor: 3.164
View more
  12 in total

1.  Antibacterial activity in serum of the 3,5-diamino-piperidine translation inhibitors.

Authors:  Yuefen Zhou; Chun Chow; Douglas E Murphy; Zhongxiang Sun; Thomas Bertolini; Jamie M Froelich; Stephen E Webber; Thomas Hermann; Daniel Wall
Journal:  Bioorg Med Chem Lett       Date:  2008-04-13       Impact factor: 2.823

2.  A modular approach to synthetic RNA binders of the hepatitis C virus internal ribosome entry site.

Authors:  Maia Carnevali; Jerod Parsons; David L Wyles; Thomas Hermann
Journal:  Chembiochem       Date:  2010-07-05       Impact factor: 3.164

3.  Two novel piperidones induce apoptosis and antiproliferative effects on human prostate and lymphoma cancer cell lines.

Authors:  Risa Mia Swain; Lisett Contreras; Armando Varela-Ramirez; Mohammad Hossain; Umashankar Das; Carlos A Valenzuela; Manuel L Penichet; Jonathan R Dimmock; Renato J Aguilera
Journal:  Invest New Drugs       Date:  2022-07-06       Impact factor: 3.651

4.  A fluorescence-based screen for ribosome binding antibiotics.

Authors:  Derrick Watkins; F A Norris; Sunil Kumar; Dev P Arya
Journal:  Anal Biochem       Date:  2012-12-19       Impact factor: 3.365

5.  Novel insights of structure-based modeling for RNA-targeted drug discovery.

Authors:  Lu Chen; George A Calin; Shuxing Zhang
Journal:  J Chem Inf Model       Date:  2012-09-21       Impact factor: 4.956

Review 6.  Frameworks for targeting RNA with small molecules.

Authors:  Aline Umuhire Juru; Amanda E Hargrove
Journal:  J Biol Chem       Date:  2020-12-20       Impact factor: 5.157

7.  Aminoglycosides: molecular insights on the recognition of RNA and aminoglycoside mimics.

Authors:  Maruthi Chittapragada; Sarah Roberts; Young Wan Ham
Journal:  Perspect Medicin Chem       Date:  2009-04-28

8.  Methyl 4-(4-fluoro-anilino)-1,2,6-tris-(4-fluoro-phen-yl)-1,2,5,6-tetra-hydro-pyri-dine-3-carboxyl-ate.

Authors:  Sumati Anthal; Goutam Brahmachari; Suvankar Das; Rajni Kant; Vivek K Gupta
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-02-09

9.  Ethyl 2,6-bis-(4-chloro-phen-yl)-4-(4-fluoro-anilino)-1-(4-fluoro-phen-yl)-1,2,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

Authors:  Sumati Anthal; Goutam Brahmachari; Suvankar Das; Rajni Kant; Vivek K Gupta
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-03-09

10.  Highly functionalized piperidines: Free radical scavenging, anticancer activity, DNA interaction and correlation with biological activity.

Authors:  Suvankar Das; Cristiane J da Silva; Marina de M Silva; Maria Dayanne de A Dantas; Ângelo de Fátima; Ana Lúcia T Góis Ruiz; Cleiton M da Silva; João Ernesto de Carvalho; Josué C C Santos; Isis M Figueiredo; Edeildo F da Silva-Júnior; Thiago M de Aquino; João X de Araújo-Júnior; Goutam Brahmachari; Luzia Valentina Modolo
Journal:  J Adv Res       Date:  2017-10-31       Impact factor: 10.479
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.