Literature DB >> 27191617

3-(Benzodioxan-2-ylmethoxy)-2,6-difluorobenzamides bearing hydrophobic substituents at the 7-position of the benzodioxane nucleus potently inhibit methicillin-resistant Sa and Mtb cell division.

Valentina Straniero1, Marco Pallavicini1, Giuseppe Chiodini1, Carlo Zanotto2, Luca Volontè2, Antonia Radaelli3, Cristiano Bolchi1, Laura Fumagalli1, Maurizio Sanguinetti4, Giulia Menchinelli4, Giovanni Delogu4, Basem Battah4, Carlo De Giuli Morghen5, Ermanno Valoti6.   

Abstract

Lipophilic substituents at benzodioxane C (7) of 3-(benzodioxan-2-ylmethoxy)-2,6-difluorobenzamide improve the antibacterial activity against methicillin-resistant Staphylococcus aureus strains to MIC values in the range of 0.2-2.5 μg/mL, whereas hydrophilic substituents at the same position and modifications at the benzodioxane substructure, excepting for replacement with 2-cromanyl, are deleterious. Some of the lead compounds also exhibit good activity against Mtb. Parallel SARs to those of 3-(2-benzothiazol-2-ylmethoxy)-2,6-difluorobenzamide, well known FtsZ inhibitor, and cells alterations typical of FtsZ inhibition indicate such a protein as the target of these potent antibacterial benzodioxane-benzamides.
Copyright © 2016 Elsevier Masson SAS. All rights reserved.

Entities:  

Keywords:  2,6-Difluorobenzamide; Antibacterial activity; Benzodioxane; FtsZ; Methicillin resistance; Mycobacterium tuberculosis; Staphylococcus aureus

Mesh：

Substances：

Year:  2016        PMID： 27191617     DOI： 10.1016/j.ejmech.2016.03.068

Source DB:  PubMed          Journal:  Eur J Med Chem        ISSN： 0223-5234            Impact factor:   6.514


  8 in total

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Journal:  Antibiotics (Basel)       Date:  2021-04-15

2.  Design and characterization of chionodracine-derived antimicrobial peptides with enhanced activity against drug-resistant human pathogens.

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3.  Resolution via diastereomeric amides of enantiopure 1,4-benzoxathian-2- and 3-carboxylic acids and determination of their configuration.

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Journal:  Chirality       Date:  2022-05-20       Impact factor: 2.183

4.  Structural Variations in the Central Heterocyclic Scaffold of Tripartite 2,6-Difluorobenzamides: Influence on Their Antibacterial Activity against MDR Staphylococcus aureus.

Authors:  Thibaut Barbier; Cédric Badiou; Floriane Davy; Yves Queneau; Oana Dumitrescu; Gérard Lina; Laurent Soulère
Journal:  Molecules       Date:  2022-10-05       Impact factor: 4.927

5.  Determinants for α4β2 vs. α3β4 Subtype Selectivity of Pyrrolidine-Based nAChRs Ligands: A Computational Perspective with Focus on Recent cryo-EM Receptor Structures.

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Journal:  Molecules       Date:  2021-06-12       Impact factor: 4.411

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Authors:  Guilherme Felipe Dos Santos Fernandes; Paula Carolina de Souza; Elsa Moreno-Viguri; Mery Santivañez-Veliz; Rocio Paucar; Silvia Pérez-Silanes; Konstantin Chegaev; Stefano Guglielmo; Loretta Lazzarato; Roberta Fruttero; Chung Man Chin; Patricia Bento da Silva; Marlus Chorilli; Mariana Cristina Solcia; Camila Maríngolo Ribeiro; Caio Sander Paiva Silva; Leonardo Biancolino Marino; Priscila Longhin Bosquesi; Debbie M Hunt; Luiz Pedro S de Carvalho; Carlos Alberto de Souza Costa; Sang Hyun Cho; Yuehong Wang; Scott Gary Franzblau; Fernando Rogério Pavan; Jean Leandro Dos Santos
Journal:  J Med Chem       Date:  2017-10-16       Impact factor: 7.446

7.  Benzamide Derivatives Targeting the Cell Division Protein FtsZ: Modifications of the Linker and the Benzodioxane Scaffold and Their Effects on Antimicrobial Activity.

Authors:  Valentina Straniero; Lorenzo Suigo; Andrea Casiraghi; Victor Sebastián-Pérez; Martina Hrast; Carlo Zanotto; Irena Zdovc; Carlo De Giuli Morghen; Antonia Radaelli; Ermanno Valoti
Journal:  Antibiotics (Basel)       Date:  2020-04-04

8.  A Repurposing Approach for Uncovering the Anti-Tubercular Activity of FDA-Approved Drugs with Potential Multi-Targeting Profiles.

Authors:  Basem Battah; Giulia Chemi; Stefania Butini; Giuseppe Campiani; Simone Brogi; Giovanni Delogu; Sandra Gemma
Journal:  Molecules       Date:  2019-11-29       Impact factor: 4.411
  8 in total

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