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Literature DB >> 27994751

Identification of N-(2-Phenoxyethyl)imidazo[1,2-a]pyridine-3-carboxamides as New Antituberculosis Agents.

Zhaoyang Wu¹, Yu Lu², Linhu Li¹, Rui Zhao¹, Bin Wang², Kai Lv³, Mingliang Liu¹, Xuefu You¹.

Abstract

A series of imidazo[1,2-a]pyridine carboxamides (IPAs) bearing an N-(2-phenoxyethyl) moiety was designed and synthesized as new antitubercular agents. Seven 2,6-dimethyl IPAs demonstrated excellent in vitro activity (MIC: 0.025-0.054 μg/mL) against the drug susceptive H37Rv strain and two clinically isolated multidrug-resistant Mycobacterium tuberculosisstrains. Compound 10j displayed acceptable safety and pharmacokinetic properties, opening a new direction for further development.

Entities: Chemical

Keywords: Antitubercular agents; MTB H37Rv; N-(2-phenoxyethyl)imidazo[1,2-a]pyridine carboxamides; multidrug resistant-MTB; structure−activity relationship

Year: 2016 PMID： 27994751 PMCID： PMC5150680 DOI： 10.1021/acsmedchemlett.6b00330

Source DB: PubMed Journal: ACS Med Chem Lett ISSN： 1948-5875 Impact factor: 4.345

12 in total

1. Global action against multidrug-resistant tuberculosis.

Authors: D Schraufnagel; J Abubaker
Journal: JAMA Date: 2000-01-05 Impact factor: 56.272

2. Infectious disease. Approval of novel TB drug celebrated--with restraint.

Authors: Jon Cohen
Journal: Science Date: 2013-01-11 Impact factor: 47.728

3. Tuberculosis success.

Authors: Dan Jones
Journal: Nat Rev Drug Discov Date: 2013-03 Impact factor: 84.694

4. Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.

Authors: L Collins; S G Franzblau
Journal: Antimicrob Agents Chemother Date: 1997-05 Impact factor: 5.191

5. Design, synthesis, and in vitro antibacterial activity of fluoroquinolone derivatives containing a chiral 3-(alkoxyimino)-2-(aminomethyl)azetidine moiety.

Authors: Kai Lv; Yexin Sun; Lanyin Sun; Zengquan Wei; Huiyuan Guo; Jinwei Wu; Mingliang Liu
Journal: ChemMedChem Date: 2012-05-25 Impact factor: 3.466

6. Advent of Imidazo[1,2-a]pyridine-3-carboxamides with Potent Multi- and Extended Drug Resistant Antituberculosis Activity.

Authors: Garrett C Moraski; Lowell D Markley; Philip A Hipskind; Helena Boshoff; Sanghyun Cho; Scott G Franzblau; Marvin J Miller
Journal: ACS Med Chem Lett Date: 2011-06-09 Impact factor: 4.345

7. Clofazimine analogs with efficacy against experimental tuberculosis and reduced potential for accumulation.

Authors: Yu Lu; Meiqin Zheng; Bin Wang; Lei Fu; Weijie Zhao; Peng Li; Jian Xu; Hui Zhu; Haixia Jin; Dali Yin; Haihong Huang; Anna M Upton; Zhenkun Ma
Journal: Antimicrob Agents Chemother Date: 2011-08-15 Impact factor: 5.191

8. Lead optimization of a novel series of imidazo[1,2-a]pyridine amides leading to a clinical candidate (Q203) as a multi- and extensively-drug-resistant anti-tuberculosis agent.

Authors: Sunhee Kang; Ryang Yeo Kim; Min Jung Seo; Saeyeon Lee; Young Mi Kim; Mooyoung Seo; Jeong Jea Seo; Yoonae Ko; Inhee Choi; Jichan Jang; Jiyoun Nam; Seijin Park; Hwankyu Kang; Hyung Jun Kim; Jungjun Kim; Sujin Ahn; Kevin Pethe; Kiyean Nam; Zaesung No; Jaeseung Kim
Journal: J Med Chem Date: 2014-06-17 Impact factor: 7.446

9. High content screening identifies decaprenyl-phosphoribose 2' epimerase as a target for intracellular antimycobacterial inhibitors.

Authors: Thierry Christophe; Mary Jackson; Hee Kyoung Jeon; Denis Fenistein; Monica Contreras-Dominguez; Jaeseung Kim; Auguste Genovesio; Jean-Philippe Carralot; Fanny Ewann; Eun Hye Kim; Sae Yeon Lee; Sunhee Kang; Min Jung Seo; Eun Jung Park; Henrieta Skovierová; Ha Pham; Giovanna Riccardi; Ji Youn Nam; Laurent Marsollier; Marie Kempf; Marie-Laure Joly-Guillou; Taegwon Oh; Won Kyung Shin; Zaesung No; Ulf Nehrbass; Roland Brosch; Stewart T Cole; Priscille Brodin
Journal: PLoS Pathog Date: 2009-10-30 Impact factor: 6.823

10. Identification of novel imidazo[1,2-a]pyridine inhibitors targeting M. tuberculosis QcrB.

Authors: Katherine A Abrahams; Jonathan A G Cox; Vickey L Spivey; Nicholas J Loman; Mark J Pallen; Chrystala Constantinidou; Raquel Fernández; Carlos Alemparte; Modesto J Remuiñán; David Barros; Lluis Ballell; Gurdyal S Besra
Journal: PLoS One Date: 2012-12-31 Impact factor: 3.240

8 in total

Review 8. Terminal Phenoxy Group as a Privileged Moiety of the Drug Scaffold-A Short Review of Most Recent Studies 2013-2022.

Authors: Paweł Kozyra; Monika Pitucha
Journal: Int J Mol Sci Date: 2022-08-09 Impact factor: 6.208

8 in total

Identification of N-(2-Phenoxyethyl)imidazo[1,2-a]pyridine-3-carboxamides as New Antituberculosis Agents.

1. Global action against multidrug-resistant tuberculosis.

2. Infectious disease. Approval of novel TB drug celebrated--with restraint.

3. Tuberculosis success.

4. Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.

5. Design, synthesis, and in vitro antibacterial activity of fluoroquinolone derivatives containing a chiral 3-(alkoxyimino)-2-(aminomethyl)azetidine moiety.

6. Advent of Imidazo[1,2-a]pyridine-3-carboxamides with Potent Multi- and Extended Drug Resistant Antituberculosis Activity.

7. Clofazimine analogs with efficacy against experimental tuberculosis and reduced potential for accumulation.

8. Lead optimization of a novel series of imidazo[1,2-a]pyridine amides leading to a clinical candidate (Q203) as a multi- and extensively-drug-resistant anti-tuberculosis agent.

9. High content screening identifies decaprenyl-phosphoribose 2' epimerase as a target for intracellular antimycobacterial inhibitors.

10. Identification of novel imidazo[1,2-a]pyridine inhibitors targeting M. tuberculosis QcrB.

Review 1. Molecule Property Analyses of Active Compounds for Mycobacterium tuberculosis.

2. Preparation and Evaluation of Potent Pentafluorosulfanyl-Substituted Anti-Tuberculosis Compounds.

3. Design, synthesis and anti-mycobacterial evaluation of imidazo[1,2-a]pyridine analogues.

4. Identification of N-Benzyl 3,5-Dinitrobenzamides Derived from PBTZ169 as Antitubercular Agents.

Review 5. Advances in Drug Discovery of New Antitubercular Multidrug-Resistant Compounds.

Review 6. Terminal Respiratory Oxidases: A Targetables Vulnerability of Mycobacterial Bioenergetics?

7. Synthesis, study of antileishmanial and antitrypanosomal activity of imidazo pyridine fused triazole analogues.

Review 8. Terminal Phenoxy Group as a Privileged Moiety of the Drug Scaffold-A Short Review of Most Recent Studies 2013-2022.