Synthesis and evaluation of novel biaryl oxazolidinones effective against gram-positive bacterial infections

Mohr KI. History of antibiotics research. Curr Top Microbiol Immunol. 2016;398:237–72. https://doi.org/10.1007/82_2016_499

Article  CAS  PubMed  Google Scholar 

Hutchings MI, Truman AW, Wilkinson B. Antibiotics: past, present and future. Curr Opin Microbiol. 2019;51:72–80. https://doi.org/10.1016/j.mib.2019.10.008

Article  CAS  PubMed  Google Scholar 

Baran A, Kwiatkowska A, Potocki L. Antibiotics and bacterial resistance-A short story of an endless arms race. Int J Mol Sci. 2023;24:5777 https://doi.org/10.3390/ijms24065777

Article  CAS  PubMed  PubMed Central  Google Scholar 

Aslam B, Khurshid M, Arshad MI, Muzammil S, Rasool M, Yasmeen N, et al. Antibiotic resistance: one health one world outlook. Front Cell Infect Microbiol. 2021;11:771510 https://doi.org/10.3389/fcimb.2021.771510

Article  CAS  PubMed  PubMed Central  Google Scholar 

Balaji SM. Growing concern of antibiotic resistance. Indian J Dent Res. 2023;34:113 https://doi.org/10.4103/ijdr.ijdr_743_23

Article  CAS  PubMed  Google Scholar 

Bhawsar S, Kale R, Deshpande P, Yeole R, Bhagwat S, Patel M. Design and synthesis of an oral prodrug alalevonadifloxacin for the treatment of MRSA infection. Bioorg Med Chem Lett. 2021;54:128432 https://doi.org/10.1016/j.bmcl.2021.128432

Article  CAS  PubMed  Google Scholar 

Bhawsar S, Pawar S, Deshpande P, Yeole R, Chavan R, Nandanwar M, et al. WCK 4034: A promising oxazolidinone for treating gram positive infections. Bioorg Med Chem Lett. 2022;71:128842 https://doi.org/10.1016/j.bmcl.2022.128842

Article  CAS  PubMed  Google Scholar 

Bhavsar S, Ravikumar T, Gupta S, Pawar S, Dabhade S, Kayastha AK, et al. WCK 4873 (INN: Nafithromycin): Structure–activity relationship (SAR) identifying a novel lactone ketolide with activity against Streptococcus pneumoniae (SPN) and Streptococcus pyogenes (SPY). Results in Chemistry. 2023;5:100757 https://doi.org/10.1016/j.rechem.2022.100757. ISSN 2211-7156

Article  CAS  Google Scholar 

Bhavsar S, Tadiparthi R, Gupta S, et al. Design and development of efficient synthetic strategies for the chiral synthesis of novel ketolide antibiotic, nafithromycin (WCK 4873). Chem. Pap. 2023;77:3629–40. https://doi.org/10.1007/s11696-023-02725-3

Article  CAS  Google Scholar 

Bhavsar S, Tadiparthi R, Pawar S, et al. Design of novel amidoxime ketolide core and an efficient synthesis of WCK 4763: for treatment of gram-positive pneumococci. Med Chem Res. 2023;32:1726–35. https://doi.org/10.1007/s00044-023-03101-2

Article  CAS  Google Scholar 

Papp-Wallace KM, Nguyen NQ, Jacobs MR, Bethel CR, Barnes MD, Kumar V, et al. Strategic approaches to overcome resistance against gram-negative pathogens using β-lactamase inhibitors and β-lactam enhancers: activity of three novel diazabicyclooctanes WCK 5153, Zidebactam (WCK 5107), and WCK 4234. J Med Chem. 2018;61:4067–86. https://doi.org/10.1021/acs.jmedchem.8b00091

Article  CAS  PubMed  PubMed Central  Google Scholar 

Bhavsar S, Joshi S, Pawar S, et al. Structure activity relationship (SAR) driven design and discovery of WCK 5107 (Zidebactam): novel β-lactam enhancer, potent against multidrug-resistant gram-negative pathogens. Med Chem Res. 2023;32:2245–55. https://doi.org/10.1007/s00044-023-03135-6

Article  CAS  Google Scholar 

Bhavsar S, Joshi S, Deshmukh V, et al. Design and development of an efficient convergent synthetic strategy for novel β-lactam enhancer zidebactam (WCK 5107). Chem. Pap. 2024;78:1493–504. https://doi.org/10.1007/s11696-023-03176-6

Article  CAS  Google Scholar 

Fernandes GFS, Scarim CB, Kim SH, Wu J, Castagnolo D. Oxazolidinones as versatile scaffolds in medicinal chemistry. RSC Med Chem. 2023;14:823–47. https://doi.org/10.1039/d2md00415a

Article  CAS  PubMed  PubMed Central  Google Scholar 

Renslo AR. Antibacterial oxazolidinones: emerging structure-toxicity relationships. Expert Rev Anti Infect Ther. 2010;8:565–74. https://doi.org/10.1586/eri.10.26

Article  CAS  PubMed  Google Scholar 

Sood R, Bhadauriya T, Rao M, Gautam R, Malhotra S, Barman TK, et al. Antimycobacterial activities of oxazolidinones: a review. Infect Disord Drug Targets. 2006;6:343–54. https://doi.org/10.2174/187152606779025860

Article  CAS  PubMed  Google Scholar 

Brumfitt W, Hamilton-Miller JM. In-vitro microbiological activities of DuP 105 and DuP 721, novel synthetic oxazolidinones. J Antimicrob Chemother. 1988;21:711–20. https://doi.org/10.1093/jac/21.6.711

Article  CAS  PubMed  Google Scholar 

Moellering RC. Linezolid: the first oxazolidinone antimicrobial. Ann Intern Med. 2003;138:135–42. https://doi.org/10.7326/0003-4819-138-2-200301210-00015

Article  CAS  PubMed  Google Scholar 

Kearney JA, Barbadora K, Mason EO, Wald ER, Green M. In vitro activities of the oxazolidinone compounds linezolid (PNU-100766) and eperzolid (PNU-100592) against middle ear isolates of Streptococcus pneumoniae. Int J Antimicrob Agents. 1999;12:141–4. https://doi.org/10.1016/s0924-8579(99)00059-x

Article  CAS  PubMed  Google Scholar 

Plouffe JF. Emerging therapies for serious gram-positive bacterial infections: a focus on linezolid. Clin Infect Dis. 200031(Suppl 4):S144–9. https://doi.org/10.1086/314080

Article  CAS  PubMed  Google Scholar 

World Health Organization, WHO Consolidated Guidelines on Tuberculosis, Module 4: Treatment - Drug-Resistant Tuberculosis Treatment, Geneva, 2020

Conradie F, Diacon AH, Ngubane N, Howell P, Everitt D, Crook AM, et al. Nix-TB trial team. treatment of highly drug-resistant pulmonary tuberculosis. N Engl J Med. 2020;382:893–902. https://doi.org/10.1056/NEJMoa1901814

Article  CAS  PubMed  PubMed Central  Google Scholar 

Elbarbry F, Moshirian N. Linezolid-associated serotonin toxicity: a systematic review. Eur J Clin Pharmacol. 2023;79:875–83. https://doi.org/10.1007/s00228-023-03500-9

Article  PubMed  Google Scholar 

Hoy SM. Contezolid: first approval. Drugs. 2021;81:1587–91. https://doi.org/10.1007/s40265-021-01576-0. Erratum in: Drugs. 2021 Nov;81(16):1945

Article  CAS  PubMed  PubMed Central  Google Scholar 

O’Riordan W, Green S, Mehra P, De Anda C, Fang E, Prokocimer P. Tedizolid phosphate for the management of acute bacterial skin and skin structure infections: efficacy summary. Clin Infect Dis. 2014;58(Suppl 1):S43–50. https://doi.org/10.1093/cid/cit617

Article  CAS  PubMed  Google Scholar 

Zhanel GG, Love R, Adam H, Golden A, Zelenitsky S, Schweizer F, et al. Tedizolid: a novel oxazolidinone with potent activity against multidrug-resistant gram-positive pathogens. Drugs. 2015;75:253–70. https://doi.org/10.1007/s40265-015-0352-7

Article  CAS  PubMed  Google Scholar 

Moellering RC Jr. Tedizolid: a novel oxazolidinone for Gram-positive infections. Clin Infect Dis. 2014;58(Suppl 1):S1–3. https://doi.org/10.1093/cid/cit658

Article  PubMed  Google Scholar 

Cho YS, Lim HS, Han S, Yoon SK, Kim H, Cho YL, et al. Single-dose Intravenous Safety, Tolerability, and Pharmacokinetics and Absolute Bioavailability of LCB01-0371. Clin Ther. 2019;41:92–106. https://doi.org/10.1016/j.clinthera.2018.11.009

Article  CAS  PubMed  Google Scholar 

Wallis RS, Dawson R, Friedrich SO, Venter A, Paige D, Zhu T, et al. Mycobactericidal activity of sutezolid (PNU-100480) in sputum (EBA) and blood (WBA) of patients with pulmonary tuberculosis. PLoS One. 2014;9:e94462 https://doi.org/10.1371/journal.pone.0094462

Article  PubMed  PubMed Central 

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