Literature DB >> 27025343

Design and synthesis of novel quinoxaline derivatives as potential candidates for treatment of multidrug-resistant and latent tuberculosis.

Mery Santivañez-Veliz1, Silvia Pérez-Silanes1, Enrique Torres2, Elsa Moreno-Viguri3.   

Abstract

Twenty-four quinoxaline derivatives were evaluated for their antimycobacterial activity using BacTiter-Glo microbial cell viability assay. Five compounds showed MIC values <3.1 μM and IC50 values<1.5 μM in primary screening and therefore, they were moved on for further evaluation. Compounds 21 and 18 stand out, showing MIC values of 1.6 μM and IC50 values of 0.5 and 1.0 μM, respectively. Both compounds were the most potent against three evaluated drug-resistant strains. Moreover, they exhibited intracellular activity in infected macrophages, considering log-reduction and cellular viability. In addition, compounds 16 and 21 were potent against non-replicating Mycobacterium tuberculosis and compound 21 was bactericidal. Therefore, quinoxaline derivatives could be considered for making further advances in the future development of antimycobacterial agents.
Copyright © 2016 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Antimycobacterial; Intracellular activity; Quinoxaline; Tuberculosis

Mesh：

Substances：

Year:  2016        PMID： 27025343      PMCID： PMC4856737          DOI： 10.1016/j.bmcl.2016.03.066

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


  26 in total

1.  Synthesis and antimycobacterial activity of new quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives.

Authors:  Elsa Moreno; Saioa Ancizu; Silvia Pérez-Silanes; Enrique Torres; Ignacio Aldana; Antonio Monge
Journal:  Eur J Med Chem       Date:  2010-07-03       Impact factor: 6.514

2.  Selective activity against Mycobacteriumtuberculosis of new quinoxaline 1,4-di-N-oxides.

Authors:  Esther Vicente; Silvia Pérez-Silanes; Lidia M Lima; Saioa Ancizu; Asunción Burguete; Beatriz Solano; Raquel Villar; Ignacio Aldana; Antonio Monge
Journal:  Bioorg Med Chem       Date:  2008-11-05       Impact factor: 3.641

Review 3.  Drug discovery in tuberculosis: a molecular approach.

Authors:  Partha P Mitra
Journal:  Indian J Tuberc       Date:  2012-10

4.  New 1,4-di-N-oxide-quinoxaline-2-ylmethylene isonicotinic acid hydrazide derivatives as anti-Mycobacterium tuberculosis agents.

Authors:  Enrique Torres; Elsa Moreno; Saioa Ancizu; Carlos Barea; Silvia Galiano; Ignacio Aldana; Antonio Monge; Silvia Pérez-Silanes
Journal:  Bioorg Med Chem Lett       Date:  2011-04-27       Impact factor: 2.823

5.  New 3-methylquinoxaline-2-carboxamide 1,4-di-N-oxide derivatives as anti-Mycobacterium tuberculosis agents.

Authors:  Saioa Ancizu; Elsa Moreno; Beatriz Solano; Raquel Villar; Asunción Burguete; Enrique Torres; Silvia Pérez-Silanes; Ignacio Aldana; Antonio Monge
Journal:  Bioorg Med Chem       Date:  2010-02-20       Impact factor: 3.641

6.  Synthesis and biological evaluation of new quinoxaline derivatives as antioxidant and anti-inflammatory agents.

Authors:  Asunción Burguete; Eleni Pontiki; Dimitra Hadjipavlou-Litina; Saioa Ancizu; Raquel Villar; Beatriz Solano; Elsa Moreno; Enrique Torres; Silvia Pérez; Ignacio Aldana; Antonio Monge
Journal:  Chem Biol Drug Des       Date:  2011-02-09       Impact factor: 2.817

7.  Synthesis, reduction potentials, and antitubercular activity of ring A/B analogues of the bioreductive drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).

Authors:  Andrew M Thompson; Adrian Blaser; Robert F Anderson; Sujata S Shinde; Scott G Franzblau; Zhenkun Ma; William A Denny; Brian D Palmer
Journal:  J Med Chem       Date:  2009-02-12       Impact factor: 7.446

8.  Efficacy of quinoxaline-2-carboxylate 1,4-di-N-oxide derivatives in experimental tuberculosis.

Authors:  Esther Vicente; Raquel Villar; Asunción Burguete; Beatriz Solano; Silvia Pérez-Silanes; Ignacio Aldana; Joseph A Maddry; Anne J Lenaerts; Scott G Franzblau; Sang-Hyun Cho; Antonio Monge; Robert C Goldman
Journal:  Antimicrob Agents Chemother       Date:  2008-07-14       Impact factor: 5.191

Review 9.  Elimination of intracellularly residing Mycobacterium tuberculosis through targeting of host and bacterial signaling mechanisms.

Authors:  Rajesh Jayachandran; Nicole Scherr; Jean Pieters
Journal:  Expert Rev Anti Infect Ther       Date:  2012-09       Impact factor: 5.091

10.  In vitro and in vivo antimycobacterial activities of ketone and amide derivatives of quinoxaline 1,4-di-N-oxide.

Authors:  Raquel Villar; Esther Vicente; Beatriz Solano; Silvia Pérez-Silanes; Ignacio Aldana; Joseph A Maddry; Anne J Lenaerts; Scott G Franzblau; Sang-Hyun Cho; Antonio Monge; Robert C Goldman
Journal:  J Antimicrob Chemother       Date:  2008-05-23       Impact factor: 5.790
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  3 in total

Review 1.  Potential anti-TB investigational compounds and drugs with repurposing potential in TB therapy: a conspectus.

Authors:  Adetomiwa A Adeniji; Kirsten E Knoll; Du Toit Loots
Journal:  Appl Microbiol Biotechnol       Date:  2020-05-05       Impact factor: 4.813

2.  Synthesis and Characterization of Novel 2-Acyl-3-trifluoromethylquinoxaline 1,4-Dioxides as Potential Antimicrobial Agents.

Authors:  Galina I Buravchenko; Dmitry A Maslov; Md Shah Alam; Natalia E Grammatikova; Svetlana G Frolova; Aleksey A Vatlin; Xirong Tian; Ivan V Ivanov; Olga B Bekker; Maxim A Kryakvin; Olga A Dontsova; Valery N Danilenko; Tianyu Zhang; Andrey E Shchekotikhin
Journal:  Pharmaceuticals (Basel)       Date:  2022-01-27

Review 3.  Targeting Non-Replicating Mycobacterium tuberculosis and Latent Infection: Alternatives and Perspectives (Mini-Review).

Authors:  Anna Egorova; Elena G Salina; Vadim Makarov
Journal:  Int J Mol Sci       Date:  2021-12-10       Impact factor: 5.923
  3 in total

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