Syntheses and studies of deuterated Imdiazo[1,2-a]pyridine-3-carboxamides with potent anti-tuberculosis activity and improved metabolic properties

Author:

Liu Rui,Marshall Kate,Ma Rui,Lien Thi Pham Kim,Shetye Gauri,Liu Zhihao,Cho Sanghyun,Jeong Hyunyoung,Franzblau Scott G.,Moraski Garrett C.,Miller Marvin J.

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Molecular Biology,Biochemistry

Reference38 articles.

1. Organization, W. H. Global Tuberculosis Report 2020. https://apps.who.int/iris/bitstream/handle/10665/336069/9789240013131-eng.pdf.

2. Drug-Resistant Tuberculosis 2020: Where We Stand;Iacobino;Appl. Sci.,2020

3. Advent of Imidazo[1,2-a]pyridine-3-carboxamides with Potent Multi- and Extended Drug Resistant Antituberculosis Activity;Moraski;ACS Med. Chem. Lett.,2011

4. (a) Moraski, G. C.; Markley, L. D.; Cramer, J.; Hipskind, P. A.; Boshoff, H.; Bailey, M.; Alling, T.; Ollinger, J.; Parish, T.; Miller, M. J. Advancement of Imidazo[1,2-a]pyridines with Improved Pharmacokinetics and Nanomolar Activity AgainstMycobacterium tuberculosis ACS Med. Chem. Lett., 2013, 4, 675-679. doi: 10.1021/ml400088y. (b) Ollinger, J.; Bailey, M. A.; Moraski, G. C.; Casey, A.; Florio, S.; Alling, T.; Miller, M. J.; Parish, T. A Dual Read-Out Assay to Evaluate the Potency of Compounds Active againstMycobacterium tuberculosis. PLOS ONE 8(4): e60531.https://doi.org/10.1371/journal.pone.0060531. (c) Moraski, G. C.; Miller, P. A.; Bailey, M. A.; Ollinger, J.; Parish, T.; Boshoff, H. I.; Cho, S.; Anderson, J. R.; Mulugeta, S.; Franzblau, S. G.; Miller, M. J. Putting Tuberculosis (TB) To Rest: Transformation of the Sleep Aid, Ambien, and “Anagrams” Generated Potent Antituberculosis Agents ACS Inf. Dis., 2015, 1, 85-90. https://doi.org/10.1021/id500008t. (d) Moraski, G. C.; Bristol, R.; Seeger, N.; Boshoff, H. I.; Tsang, P. S.; Miller, M. J. Preparation and Evaluation of Potent Pentafluorosulfanyl-Substituted Anti-Tuberculosis Compounds, ChemMedChem., 2017, 12, 1108-1115. https://doi.org/10.1002/cmdc.201700170.

5. Scaffold-switching: An exploration of 5,6-fused bicyclic heteroaromatics systems to afford antituberculosis activity akin to the imidazo[1,2-a]pyridine-3-carboxylates;Moraski;Bioorg. Med. Chem. Lett.,2014

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