European Journal of Chemistry 2018, 9(4), 353-359 | doi: https://doi.org/10.5155/eurjchem.9.4.353-359.1783 | Get rights and content






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A novel and expeditious synthesis of oxazolidinone drugs linezolid and eperezolid


Ranjith Siddaraj (1) orcid , Shivaraja Govindaiah (2) orcid , Raghu Ningegowda (3) orcid , Nanjunda Swamy Shivananju (4) orcid , Babu Shubha Priya (5,*) orcid

(1) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India
(2) Department of Studies and Research in Chemistry, Tumkur University, Tumkur-572103, Karnataka, India
(3) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India
(4) Department of Biotechnology, Sri Jayachamarajendra College of Engineering, JSS Technical Institutions Campus, Mysore-570006, Karnataka, India
(5) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India
(*) Corresponding Author

Received: 28 Aug 2018 | Revised: 04 Oct 2018 | Accepted: 06 Oct 2018 | Published: 31 Dec 2018 | Issue Date: December 2018

Abstract


A concise and efficient synthesis of linezolid and eperezolid were accomplished through a convergent scheme utilizing diverse reaction conditions. The synthesis demonstrates utility of a new approach to facilitate the expeditious construction of 3-aryl-5-(substituted methyl)-2-oxazolidinones and easier insertion of N-acetyl group. This new approach offers the possibility of accessing related 2-oxazolidinone members easily as well as making additional analogues of Linezolid. The adopted method afforded high purity and excellent yield compared to other existing synthetic methods. The compounds were successfully characterized by known spectroscopic techniques.


Keywords


Linezolid; Eperezolid; Acetamide; Sodium iodide; Cesium carbonate; (R)-2-(Bromomethyl)oxirane

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DOI: 10.5155/eurjchem.9.4.353-359.1783

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References

[1]. Wallace, R. J. J.; Brown-Elliott, B. A.; Ward, S. C.; Crist, C. J.; Mann, L. B.; Wilson, R. W. Antimicrob. Agents Chemother. 2001, 45, 764-767.
https://doi.org/10.1128/AAC.45.3.764-767.2001

[2]. Peters, J.; Kondo, K.; Lee, R.; Lin, C.; Inderlied, C. J. Antimicrob. Chemother. 1995, 35, 675-679.
https://doi.org/10.1093/jac/35.5.675

[3]. Vardakas, K. Z.; Kioumis, I.; Falagas, M. E. Curr. Drug Metab. 2009, 10, 2-12.
https://doi.org/10.2174/138920009787048446

[4]. Potoski, B. A.; Adams, J.; Clarke, L.; Shutt, K.; Linden, P. K.; Baxter, C.; Pasculle, A. W.; Capitano, B.; Peleg, A. Y.; Szabo, D.; Paterson, D. L. Clin. Infect. Dis. 2006, 43, 165-171.
https://doi.org/10.1086/505114

[5]. Toh, S. M.; Xiong, L.; Arias, C. A.; Villegas, M. V.; Lolans, K.; Quinn, J.; Mankin, A. S. Mol. Microbiol. 2007, 64, 1506-1514.
https://doi.org/10.1111/j.1365-2958.2007.05744.x

[6]. Roehrig, S.; Straub, A.; Pohlmann, J.; Lampe, T.; Pernerstorfer, J.; Schlemmer, K. H. Reinemer, P.; Perzborn, E. J. Med. Chem. 2005, 48, 5900-5908.
https://doi.org/10.1021/jm050101d

[7]. Kalia, V.; Miglani, R.; Purnapatre, K. P.; Mathur, T.; Singhal, S.; Khan, S.; Voleti, S. R.;Upadhyay, D. J.; Saini, K. S.; Rattan, A.; Raj, V. S. Antimicrob. Agents Chemother. 2009, 53, 1427-1433.
https://doi.org/10.1128/AAC.00887-08

[8]. Howe, R. A.; Wootton, M.; Noel, A. R.; Bowker, K. E.; Walsh, T. R.; MacGowan, A. P. Antimicrob. Agents Chemother. 2003, 47, 3651-3652.
https://doi.org/10.1128/AAC.47.11.3651-3652.2003

[9]. Livermore, D. M.; Mushtaq, S.; Warner, M.; Woodford, N. J. Antimicrob. Chemother. 2009, 63, 713-715.
https://doi.org/10.1093/jac/dkp002

[10]. Skripkin, E.; McConnell, T. S.; DeVito, J.; Lawrence, L.; Ippolito, J. A.; Duffy, E. M.; Sutcliffe, J.; Franceschi, F. Antimicrob. Agents Chemother. 2008, 52, 3550-3557.
https://doi.org/10.1128/AAC.01193-07

[11]. Brickner, S. J.; Hutchinson, D. K.; Barbachyn, M. R.; Manninen, P. R.; Ulanowicz, D. A.;Garmon, S. A.; Grega, K. C.; Hendges, S. K.; Toops, D. S.; Ford, C. W.; Zurenko, G. E. J. Med. Chem. 1996, 39, 673-679.
https://doi.org/10.1021/jm9509556

[12]. Barbachyn, M. R.; Brickner, S. J.; Hutchinson, D. K. U.S. patent 5688792; 1997; Chem. Abstr. 1995, 123, 256742.

[13]. Dhananjay, G. S.; Nandu, B. B.; Avinash, V. N.; Kamlesh, D. S.; Anindya, S. B.; Tushar, A. N. PCT Int. Appl. 063505,2009; Chem. Abstr. 2009, 150, 515152.

[14]. Imbordino, R. J.; Perrault, W. R.; Reeder, M. R. PCT Int. Appl. 116284, 2007; Chem. Abstr. 2007, 147, 469356.

[15]. Pearlman, B. A.; Perrault, W. R.; Barbachyn, M. R.; Manninen, P. R.; Toops, D. S.; Houser, D. J.; Fleck, T. J. U.S. Patent 5837870, 1998; Chem. Abstr. 1998, 130, 25061.

[16]. Perrault, W. R.; Pearlman, B. A.; Godrej, D. B.; Jeganathan, A.;Yamagata, K.; Chen, J. J.; Lu, C. V.; Herrinton, P.M.; Gadwood, R. C.; Chan, L.; Lyster, M. A.; Maloney, M. T.; Moeslein, J. A.; Greene, M. L.; Barbachyn, M. R. Org. Proc. Res. Dev. 2003, 7, 533-546.
https://doi.org/10.1021/op034028h

[17]. Yu, D. S.; Huang, L.; Liang, H.; Gong, P. Chin. Chem. Lett. 2005, 16, 875-878.

[18]. Pearlman, B. A. PCT Int. Appl. 9924393, 1999; Chem. Abstr. 1999, 130, 338099.

[19]. Wang, M.; Tong, H. CN patent 101220001, 2008.

[20]. Mohan-Rao, D.; Krishna, R. P. PCT Int. Appl. 099353, 2005; Chem. Abstr. 2005, 143, 440395.

[21]. Mohan-Rao, D.; Krishna, R. P. PCT Int. Appl. 008754, 2006; Chem. Abstr. 2006, 144, 170978.

[22]. Madhusudhan, G.; Om Reddy, G.; Ramanatham, J.; Dubey, P. K. Indian J. Chem. 2005, 44B, 1236-1238.

[23]. Madhusudhan, G.; Om Reddy, G.; Rajesh, T.; Ramanatham, J.; Dubey, P. K. Tetrahedron Lett. 2008, 49, 3060-3062.
https://doi.org/10.1016/j.tetlet.2008.03.061

[24]. Rajesh, T.; Narayana Rao, S. P.; Suresh, K. Madhusudhan, G.; Mukkanti, K. J. Hetercyclic Chem. 2010, 47, 1392-1397.
https://doi.org/10.1002/jhet.494

[25]. Moran-Ramallal, R.; Liz, R.; Gotor, V. Org. Lett. 2008, 10, 1935-1938.
https://doi.org/10.1021/ol800443p

[26]. Mallesham, B.; Rajesh, B. M.; Rajamohan, R. P.; Srinivas, D.; Sanjay, T. Org. Lett. 2003, 5, 963-965.
https://doi.org/10.1021/ol026902h

[27]. Selvakumar, N.; Srinivas, D.; Manoj, K. K.; Sitaram, K. M.; Mamidi, R. N. V. S.; Hemanth, S.; Chandrashekar, C.; Srinivasa Rao, B.; Mohammed, R. A.; Jagattaran, D.; Javed, I.; Raagopalan, R. J. Med. Chem. 2002, 45, 3953-3962.
https://doi.org/10.1021/jm020092y

[28]. Tokuyama, R.; Takahashi, Y.; Tomita, Y.; Tsubouchi, M.; Yoshida, T.; Iwasaki, N.; Kado, N.; Okezaki, E.; Nagata, O. Chem. Pharm. Bull. 2001, 49, 361-367.
https://doi.org/10.1248/cpb.49.361

How to cite


Siddaraj, R.; Govindaiah, S.; Ningegowda, R.; Shivananju, N.; Priya, B. Eur. J. Chem. 2018, 9(4), 353-359. doi:10.5155/eurjchem.9.4.353-359.1783
Siddaraj, R.; Govindaiah, S.; Ningegowda, R.; Shivananju, N.; Priya, B. A novel and expeditious synthesis of oxazolidinone drugs linezolid and eperezolid. Eur. J. Chem. 2018, 9(4), 353-359. doi:10.5155/eurjchem.9.4.353-359.1783
Siddaraj, R., Govindaiah, S., Ningegowda, R., Shivananju, N., & Priya, B. (2018). A novel and expeditious synthesis of oxazolidinone drugs linezolid and eperezolid. European Journal of Chemistry, 9(4), 353-359. doi:10.5155/eurjchem.9.4.353-359.1783
Siddaraj, Ranjith, Shivaraja Govindaiah, Raghu Ningegowda, Nanjunda Swamy Shivananju, & Babu Shubha Priya. "A novel and expeditious synthesis of oxazolidinone drugs linezolid and eperezolid." European Journal of Chemistry [Online], 9.4 (2018): 353-359. Web. 10 Aug. 2020
Siddaraj, Ranjith, Govindaiah, Shivaraja, Ningegowda, Raghu, Shivananju, Nanjunda, AND Priya, Babu. "A novel and expeditious synthesis of oxazolidinone drugs linezolid and eperezolid" European Journal of Chemistry [Online], Volume 9 Number 4 (31 December 2018)

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