Synthesis of Oxazolidinone Phosphonates as Antibacterial Agents

Jae-Min Hwang; Sung-Ho Yeom; Kang-Yeoun Jung

Journal of Industrial and Engineering Chemistry, Vol.13, No.3, 474-479, May, 2007

Export Citation

Synthesis of Oxazolidinone Phosphonates as Antibacterial Agents

Jae-Min Hwang, Sung-Ho Yeom , and Kang-Yeoun Jung^†

Department of Environmental & Applied Chemistry, College of Engineering, Kangnung National University, Kangwondo 210-702, Korea

E-mail:

Several oxazolidinones, which are a new class of synthetic antibacterial agents, display biological activity against multidrug-resistant Gram-positive organisms such as Staphylococci, Streptococci, and Enterococci. In the course of our studies directed toward the discovery of novel antibacterial agents, which are expected to have improved drug efficacy and better toxicity profiles than Linezolid, we synthesized new derivatives of oxazolidinone phosphonates efficiently from commercially available L-serine. These compounds were tested for their in vitro antibacterial activity; one of the compounds showed promising activity, which we will pursue in further studies.

Keywords:phosphonic acid;oxazolidinone;antibacterial;L-serine

[References]

Brickner SJ, Curr. Pharm. Des., 2, 175 (1996)
Barbachyn MR, Ford CW, Angew. Chem.-Int. Edit., 42, 2010 (2003)
Hutchinson DK, Curr. Top. Med. Chem., 3, 1021 (2003)
Nilus AM, Curr. Opin. Invest. Drugs, 4, 149 (2003)
Slee AM, Wuonola MA, McRipley RJ, Zajac I, Zawada MJ, Batholomew PT, Gregory WA, Forbes M, Abstracts of 27th Interscience Conference on Antimicrobial Agents and Chemotherapy, New York, Oct. 4-7, abstract No. 244 (1987)
Brickner SJ, Hutchinson DK, Barbachyn MR, Manninen PR, Ulanowicz DA, Garmon SA, Grega KC, Hendges SK, Toops DS, Ford CW, Zurenko GE, J. Med. Chem., 39, 673 (1996)
Gonzales RD, Schreckenberger PC, Graham MB, Kelkar S, DenBesten K, Quinn JP, Lancet, 357, 1179 (2001)
Tsiodras S, Gold HS, Sakoulas G, Eliopoulas GM, Wennerstein C, Venkatraman LR, Moellering C, Ferro MJ, Lancet, 358, 207 (2001)
Ford W, Zurenko CGE, Barbachyn MR, Curr. Drug Targets: Infect. Disord., 1, 181 (2001)
Jung KY, Hwang JM, Bull. Korean Chem. Soc., 25(9), 1326 (2004)
Jung KY, Lee MY, McClure CK, Phosphorus Sulfur Silicon, 147, 141 (1999)
McClure CK, Hausel RC, Hansen KB, Grote CW, Jung KY, Phosphorus Sulfur Silicon, 111, 63 (1996)
McClure CK, Jung KY, J. Org. Chem., 56, 867 (1991)
Jung KY, Lee MY, J. Ind. Eng. Chem., 5(3), 224 (1999)
Herweh JE, Kauffman W, Tetrahedron Lett., 809 (1971)
Cardillo G, Orena M, Sandri S, J. Org. Chem., 51, 713 (1986)
Gregory WA, Brittelli DR, Wang CLJ, Kezar HS, Carlson RK, Park CH, Corless PF, Miller SJ, Rajagopalan P, Wuonola MA, McRipley RJ, Eberly VS, Slee AM, Forbes M, J. Med. Chem., 33, 2569 (1990)
Sibi MP, Renhowe PA, Tetrahedron Lett., 31, 7407 (1990)
Sibi MP, Rutherford D, Renhowe PA, Li BQ, J. Am. Chem. Soc., 121(33), 7509 (1999)
Neri C, Williams JM, J. Adv. Synth. Catal., 345, 835 (2003)
NCCLS. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically: approved standard, 6th Edn., NCCLS document M7- A6 (ISBN 1-56238-486-4). NCCLS, Pennsylvania, USA (2003)

[Referenced By]

[Related Articles]

[1] Brickner SJ, Curr. Pharm. Des., 2, 175 (1996)

[2] Barbachyn MR, Ford CW, Angew. Chem.-Int. Edit., 42, 2010 (2003)

[3] Hutchinson DK, Curr. Top. Med. Chem., 3, 1021 (2003)

[4] Nilus AM, Curr. Opin. Invest. Drugs, 4, 149 (2003)

[5] Slee AM, Wuonola MA, McRipley RJ, Zajac I, Zawada MJ, Batholomew PT, Gregory WA, Forbes M, Abstracts of 27th Interscience Conference on Antimicrobial Agents and Chemotherapy, New York, Oct. 4-7, abstract No. 244 (1987)

[6] Brickner SJ, Hutchinson DK, Barbachyn MR, Manninen PR, Ulanowicz DA, Garmon SA, Grega KC, Hendges SK, Toops DS, Ford CW, Zurenko GE, J. Med. Chem., 39, 673 (1996)

[7] Gonzales RD, Schreckenberger PC, Graham MB, Kelkar S, DenBesten K, Quinn JP, Lancet, 357, 1179 (2001)

[8] Tsiodras S, Gold HS, Sakoulas G, Eliopoulas GM, Wennerstein C, Venkatraman LR, Moellering C, Ferro MJ, Lancet, 358, 207 (2001)

[9] Ford W, Zurenko CGE, Barbachyn MR, Curr. Drug Targets: Infect. Disord., 1, 181 (2001)

[10] Jung KY, Hwang JM, Bull. Korean Chem. Soc., 25(9), 1326 (2004)

[11] Jung KY, Lee MY, McClure CK, Phosphorus Sulfur Silicon, 147, 141 (1999)

[12] McClure CK, Hausel RC, Hansen KB, Grote CW, Jung KY, Phosphorus Sulfur Silicon, 111, 63 (1996)

[13] McClure CK, Jung KY, J. Org. Chem., 56, 867 (1991)

[14] Jung KY, Lee MY, J. Ind. Eng. Chem., 5(3), 224 (1999)

[15] Herweh JE, Kauffman W, Tetrahedron Lett., 809 (1971)

[16] Cardillo G, Orena M, Sandri S, J. Org. Chem., 51, 713 (1986)

[17] Gregory WA, Brittelli DR, Wang CLJ, Kezar HS, Carlson RK, Park CH, Corless PF, Miller SJ, Rajagopalan P, Wuonola MA, McRipley RJ, Eberly VS, Slee AM, Forbes M, J. Med. Chem., 33, 2569 (1990)

[18] Sibi MP, Renhowe PA, Tetrahedron Lett., 31, 7407 (1990)

[19] Sibi MP, Rutherford D, Renhowe PA, Li BQ, J. Am. Chem. Soc., 121(33), 7509 (1999)

[20] Neri C, Williams JM, J. Adv. Synth. Catal., 345, 835 (2003)

[21] NCCLS. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically: approved standard, 6th Edn., NCCLS document M7- A6 (ISBN 1-56238-486-4). NCCLS, Pennsylvania, USA (2003)