Skip to main content

Advertisement

Log in

RETRACTED ARTICLE: Design, synthesis of novel oxazolidino-amides/sulfonamides conjugates and their impact on antibacterial activity

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

This article was retracted on 11 November 2021

This article has been updated

Abstract

In view of generating new compounds for future drug development, we have synthesized oxazolidinones library of aryl amides and aryl sulfonamide derivatives. These compounds were screened in vitro against panel of susceptible and resistant Gram-positive (Staphylococcus aureus and Bacillus subtilis), Gram-negative bacteria (Pseudomonas aeruginosa), fungi (Candida albicans) strains, and Mycobacterium tuberculosis (Mtb). Among them, 10d and 11a compounds have been evaluated against 12 fungal strains and have displayed significant antimycotic activities approximately 37 folds more potent than fluconazole.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Scheme 2

Similar content being viewed by others

Change history

References

  • Amsterdam D, Loman V (1996) Antibiotics in laboratory medicine, 4. Williams and Wilkins, Baltimore, pp 52–111

    Google Scholar 

  • Aoki H, Ke L, Poppe SM, Poel TJ, Weaver EA, Gadwood RC, Thomas RC, Shinabarger DL, Ganoza MC (2002) Oxazolidinone antibiotics target the P site on Escherichia coli ribosomes. Antimicrob Agents Chemother 46:1080–1085

    Article  CAS  Google Scholar 

  • Apodaca AAA, Rakita RM (2003) Linezolid-induced lactic acidosis. N Engl J Med 348:86–87. doi:10.1056/NEJM200301023480123

    Article  PubMed  Google Scholar 

  • Barbachyn MR, Ford CW (2003) Oxazolidinone structure–activity relationships leading to linezolid. Angew Chem Int Ed 42:2010–2023. doi:10.1002/anie.200200528

    Article  CAS  Google Scholar 

  • Barbachyn MR, Brickner SJ, Hutchinson D (1997) US 5688792. Chem Abstr (1995) 123:256742

    Google Scholar 

  • Barbachyn MR, Morris J, Wishka DG, Thomas RC, Graber DR (1999) PCT W0199943671

  • Bergeron L, Boule M, Perreeault S (2005) Serotonin toxicity associated with concomitant use of linezolid. Ann Pharmacother 39:956–961. doi:10.1345/aph.1E523

    Article  PubMed  Google Scholar 

  • Bobkova EV, Van YP, Jordan DB, Kurilla MG, Pompliano DL (2003) Catalytic properties of mutant 23 S ribosomes resistant to oxazolidinones. J Biol Chem 278:9802–9807

    Article  CAS  Google Scholar 

  • Boyer FE, Prasad JVNV, Choy AL, Chupak L, Dermyer MR, Ding Q, Huband MD, Jiao W, Kaneko T, Khlebnikov V (2007) Synthesis and SAR of novel conformationally-restricted oxazolidinones possessing Gram-positive and fastidious Gram-negative antibacterial activity. Part 1: substituted pyrazoles. Bioorg Med Chem Lett 17:4694–4698. doi:10.1016/j.bmcl.2007.05.056

    Article  CAS  PubMed  Google Scholar 

  • Bressler AM, Zimmer SM, Gilmore JL, Somani J (2004) Peripheral neuropathy associated with prolonged use of linezolid. Lancet Infect Dis 4:528–531. doi:10.1016/S1473-3099(04)01109-0

    Article  PubMed  Google Scholar 

  • Brickner SJ (1996) Oxazolidinone antibacterial agents. Curr Pharm Des 2:175–194

    CAS  Google Scholar 

  • Brickner SJ (2007) Linezolid (ZYVOX), the First member of a completely new class of antibacterial agents for treatment of serious gram-positive infections. Compr Med Chem II. 8:157–172

    Google Scholar 

  • Cano M, Palomer A, Guglietta A (2006) Preparation of oxazolidinone compounds and compositions for the treatment of bacterial infections. From PCT Int. Appl. WO 2006010756 A1 Feb 02, 2006

  • Chen Y, Ruan ZX, Wang F, Huangfu DS, Sun PH, Lin J, Chen WM (2015) Novel oxazolidinone antibacterial analogues with a substituted ligustrazine C-ring unit. Chem Biol Drug Des 86:682–690. doi:10.1111/cbdd.12537

    Article  CAS  PubMed  Google Scholar 

  • Cooper CB, Huang H, Zhang D, Fotouhi N, Kaneko T (2017) Preparation of substituted phenyl oxazolidinones for antimicrobial therapy. PCT Int Appl WO 2017015106A1 Jan 26, 2017

  • Das B, Rajarao AVS, Rudra S, Yadav A, Ray A, Pandya M, Rattan A, Mehta A (2009) Synthesis and biological activity of novel oxazolidinones. Bioorg Med Chem Lett 19:6424–6428. doi:10.1016/j.bmcl.2009.09.054

    Article  CAS  PubMed  Google Scholar 

  • Ford CW, Zurenko GE, Barbacyn MR (2001) The discovery of linezolid, the first oxazolidinone antibacterial agent. Curr Drug Target. doi:10.2174/1568005014606099

    Article  Google Scholar 

  • Fridkin SK, Edwards JR, Courval JM, Hill H, Tenover FC, Lawton R, Gaynes RP, McGowan JE (2001) The effect of vancomycin and third-generation cephalosporins on prevalence of vancomycin-resistant Enterococci in 126 U.S. adult intensive care units. Ann Intern Med 135:175–183. doi:10.7326/0003-4819-135-3-200108070-00009

    Article  CAS  PubMed  Google Scholar 

  • Gillman PK (2003) Linezolid and serotonin toxicity. Clin Infect Dis 37:1274–1275. doi:10.1086/378895

    Article  PubMed  Google Scholar 

  • Hutchinson DK (2003) Oxazolidinone antibacterial agents: a critical review. Curr Top Med Chem 3:1021–1042. doi:10.2174/1568026033452195

    Article  CAS  PubMed  Google Scholar 

  • Johnson AP, Tysall L, Stockdale M, Woodford N, Kanufmann ME, Warner M, Livermore DM, Asboth F, Allerberger FJ (2002) Emerging linezolid resistant Enterococcus faecalis and Enterococcus faecium isolated from two Austrian patients in the same intensive care unit. Eur J Clin Microbiol Infect Dis 21:751–754. doi:10.1007/s10096-002-0807-0

    Article  CAS  PubMed  Google Scholar 

  • Joseph AI, Zoltan FK, Deping W, Francosis JF, Peter BM, Thomas AS, Erin MD (2008) Crystal structure of the oxazolidinone antibiotic linezolid bound to the 50s ribosomal subunit. J Med Chem 51:3353–3356. doi:10.1021/jm800379d

    Article  CAS  Google Scholar 

  • Kalamazoo Ml (2003) Zyvox Pharmacia & Upjohn. http://www.pfizer.com/files/priducts/uspizyvox.pdf

  • Kuter DJ, Tilloston GS (2001) Hematologic effects of antimicrobials: focus on the oxazolidinone linezolid. Pharmacotheraphy 21:1010–1013. doi:10.1592/phco.21.11.1010.34517

    Article  CAS  Google Scholar 

  • Leclercq R, Derlot E, Duval J, Courvalin P (1988) Plasmid-mediated resistance to vancomycin and Teicoplanin in Enterococcus faecium. N Engl J Med 319:157–161. doi:10.1056/NEJM198807213190307

    Article  CAS  PubMed  Google Scholar 

  • Lin AH, Murray RW, Vidmar TJ, Marotti KR (1997) The oxazolidinone eperezolid binds to the 50S ribosomal subunit and competes with binding of chloramphenicol and lincomycin. Antimicrob Agents Chemother 41:2127–2131

    Article  CAS  Google Scholar 

  • Martone WJ, Jarvis WR, Edwards JR, Culver D, Haley RW (1998) Incidence and nature of endemic and epidemic nosocomial infections. In: Bennett JV, Brachman PS (eds) Hospital infections, 4th edn. Lippincott Williams and Wilkins, Philadelphia, p 461– 476

  • Matassaova NB, Rodnina MV, Endermann R, Kroll HP, Pleiss U, Wild H, Wintermeyer W (1999) Ribosomal RNA is the target for oxazolidinones, a novel class of translational inhibitors. RNA 5:939–946

    Article  Google Scholar 

  • Moise PA, Forrest A, Birminggham MC, Schentaq JJ (2002) The efficacy and safety of linezolid as treatment for Staphylococcus aureus infections in compassionate use patients who are intolerant of, or who have failed to respond to vancomycin. J Antimicrob Chemother 50:1017–1026. doi:10.1093/jac/dkf215

    Article  CAS  PubMed  Google Scholar 

  • Park CH, Brittelli DR, Wang CL, Marsh FD, Gregory WA, Wuonola MA, McRipley RJ, Eberly VS, Slee AM, Fobes M (1992) Antibacterials. Synthesis and structure-activity studies of 3-aryl-2-oxooxazolidines. 4 multiply-substituted aryl derivatives. J Med Chem 35:1156–1165. doi:10.1021/jm00084a022

    Article  CAS  PubMed  Google Scholar 

  • Patel U, Yan YP, Hobbs FW, Kaczmarczyk J, Slee AM, Pompliano DL, Kurilla MG, Bobkova EV (2001) Oxazolidinones mechanism of action: inhibition of the first peptide bond formation. J Biol Chem 276:37199–37205

    Article  CAS  Google Scholar 

  • Peppard WJ, Weigelt JA (2006) Role of linezolid in the treatment of complicated skin and soft tissue infections. Expert Rev Anti Infect Ther 4:357–366. doi:10.1586/14787210.4.3.357

    Article  CAS  PubMed  Google Scholar 

  • Quesnella CA, Gill P, Roy S, Dodier M, Martel A, Synder LB, D’Andrea SV, Bronson JJ, Frosco M (2005) Biaryl iso oxazolinone anti-bacterial agents. Bioorg Med Chem 15:2728–2733. doi:10.1016/j.bmcl.2005.04.003

    Article  CAS  Google Scholar 

  • Ramos DF, Leitão GG, Costa FDN, Abreu L, Villarreal JV, Leitão SG (2008) Investigation of the antimycobacterial activity of 36 plant extracts from the Brazilian Atlantic forest. Braz J Pharm Sci 44:669–674. doi:10.1590/S1516-93322008000400013

    Article  Google Scholar 

  • Roehrig S, Straub A, Pohlmann J, Lampe T, Pernerstorfer J, Schlemmer KH, Reinemer P, Perzborn E (2005) Discovery of the Novel Antithrombotic Agent 5-Chloro-N-({(5S)-2-oxo-3- [4-(3-oxomorpholin-4-yl) phenyl]-1, 3-oxazolidin-5-yl} methyl) thiophene-2-carboxamide (BAY 59-7939): an oral, direct factor Xa inhibitor. J Med Chem 48:5900–5908. doi:10.1021/jm050101d

    Article  CAS  PubMed  Google Scholar 

  • Sakoulas G, Gold HS, Venkataraman L, Moellering RC, Ferraro MJ, Eliopoulos GM (2003) Introduction of erm(C) into a linezolid- and methicillin-resistant Staphylococcus aureus does not restore linezolid susceptibility. J Antimicrob Chemother 51:1039–1041. doi:10.1093/jac/dkg194

    Article  CAS  PubMed  Google Scholar 

  • Shinabarger DL, Marotti KR, Murray RW, Lin AH, Melchior EP, Swaney SM, Dunyak DS, Demyan WF, Buysse JM (1997) Mechanism of action of oxazolidinones: effects of linezolid and eperezolid on translation reactions. Antimicrob Agents Chemother 41:2132–2136

    Article  CAS  Google Scholar 

  • Steven J, Douglas KR, Hutchison M, Barbachyn RP, Mannien AD, Ulanowicz AS (1996) Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant Gram-Positive bacterial infections. J Med Chem 39:673–679. doi:10.1021/jm9509556

    Article  Google Scholar 

  • Tsiodras S, Gold HS, Sakoulas G, Eliopouls GM, Wennersten C, Venkataraman L, Mollering RC, Ferraro M (2001) Linezolid resistance in a clinical isolate of Staphylococcus aureus. J Lancet 358:207–208. doi:10.1016/S0140-6736(01)05410-1

    Article  CAS  Google Scholar 

  • Wallace RJ Jr, Nash DR, Steele LC, Steingrube VJ (1986) Susceptibility testing of slowly growing mycobacteria by a microdilution MIC method with 7H9 broth. Clin Microbiol 24:976–981

    Article  CAS  Google Scholar 

  • Whitney CG, Farley MM, Hadler J, Harrison LH, Lexau C, Reingold A, Lefkowitz L, Cieslak PR, Zell ER, Jorgensen JH, Schuchat A (2000) Increasing prevalence of multidrug-resistant Streptococcus pneumoniae in the United States. N Engl J Med 343:1917–1924. doi:10.1056/NEJM200012283432603

    Article  CAS  PubMed  Google Scholar 

  • Wigen CL, Goetz MB (2002) Serotonin syndrome and linezolid. Clin Infect Dis 34:1651–1652. doi:10.1086/340710

    Article  PubMed  Google Scholar 

  • Zhou CC, Swaney SM, Shinabarger DL, Stockman B (2002) 1H nuclear magnetic resonance study of oxazolidinone binding to bacterial ribosomes. Antimicrob Agents Chemother 46:625–629

    Article  CAS  Google Scholar 

  • Zivkovic SA, Lacomis D (2005) Severe sensory neuropathy associated with long-term linezolid use. Neurology 64:926–927. doi:10.1212/01.WNL.0000152883.53691.5B

    Article  PubMed  Google Scholar 

  • Zurenko GE, Ford CW, Hutchinson DK, Brickner SJ, Barbachyn MR (1997) Oxazolidinone antibacterial agents: development of the clinical candidates eperezolid and linezolid. Expert Opin Investig Drugs 6:151–158. doi:10.1517/13543784.6.2.151

    Article  CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Contributions

M.V.B.Rao and R.S designed and supervised the study, Y.B synthesized and characterized compounds, and measured spectral data, biological activity was carried at CCMB (The Centre for Cellular & Molecular Biology, Hyderabad).

Corresponding author

Correspondence to Mandava. V. Basaveswara Rao.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 86 kb)

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bharath, Y., Alugubelli, G.R., Sreenivasulu, R. et al. RETRACTED ARTICLE: Design, synthesis of novel oxazolidino-amides/sulfonamides conjugates and their impact on antibacterial activity. Chem. Pap. 72, 457–468 (2018). https://doi.org/10.1007/s11696-017-0298-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11696-017-0298-1

Keywords

Navigation