RESEARCH ARTICLE

Synthesis and antimicrobial activity of 2-(aminoacid ester)-3-(6-methyl-2-pyridyl)-3,4-dihydro-2H-1,3,2 λ⁵-benzoxazaphosphinin-2-thiones

M. Anil Kumar^I; K. Suresh Kumar^I; C. Devendranath Reddy^I; C. Naga Raju^I; C. Suresh Reddy^I; P. Hari Krishna^II

^IDepartment of Chemistry, Sri Venkateswara University, Tirupati 517502, India
^IIDepartment of Plant Pathology, Sri Venkateswara Agricultural College, Angrau, Tirupati 517502, India

ABSTRACT

Synthesis of 2-(aminoacid ester)-3-(6-methyl-2-pyridyl)-3,4-dihydro-2H-1,3,2λ⁵-benzoxazaphosphinin-2-thiones (3a-j) was accomplished through a two-step process. It involves the prior preparation of 2-chloro-3-(6-methyl-2-pyridyl)-3,4-dihydro-2H-1,3,2λ⁵-benzoxazaphosphinin-2-thione monochloride (2) and its subsequent reaction with the aminoacid ester hydrochlorides in dry tetrahydrofuran-toluene in the presence of triethylamine at various temperatures. These compounds were characterized by IR, ¹H, ¹³C, ³¹P NMR and mass spectral data.

Keywords: 2-[(6-methyl-2-pyridyl) amino] methylphenol, 1,3,2-benzoxazaphosphinin-2-thione, antimicrobial activity

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Acknowledgements

The authors express their thanks to Prof. C. Eswar Reddy, Sri Venkateswara Agricultural College, Acharya N.G. Ranga University, Tirupati, for his help in antimicrobial studies and the Director, IISc, Bangalore, India, for providing spectral data.

References

1 (a) L.D. Quin, A Guide to Organophosphorus Chemistry, Wiley-Interscience, New York, NY, USA, 2000; (b) R. Engel, Handbook of Organophosphorus Chemistry, Marcel Dekker, New York, NY, USA, 1992.         [ Links ]

2 (a) F.H. Westheimer, Science, 1987, 235, 1173-1178. (b) H. Seto and T Kuzuyama, Nat. Prod. Rep., 1999, 16, 589-596.         [ Links ]

3 (a) P. Kafarski and B. Lejczak, Curr. Med. Chem., 2001, 1, 301-312; (b) O. M. Colvin, Curr. Pharm. Des., 1999, 5, 555-560; (c) M.M. Mader and P.A. Bartlett, Chem. Rev., 1997, 97, 1281-1301; (d) S.M. Ludeman, in From Nerve Agent to Anticancer Drug: The Chemistry of Phosphoramide Mustard, Biomedical Chemistry (P.F. Torrence, ed.), Wiley-Interscience, New York, NY, USA, 2000, pp. 163-187.         [ Links ]

4 J.E. Franz, M.K. Mao and J.A. Sikorski, Glyphosate: A Unique Global Herbicide, American Chemical Society, Washington, DC, USA, 1997.         [ Links ]

5 (a) B.E. Maryanoff and A.B. Reitz, Chem. Rev., 1989, 89, 863-927; (b) T. Rein and T.M. Pedersen, Synthesis, 2002, 579-594; (c) N. Brickle-bank, Organophosphorus Chem, 2003, 33, 289-320; (d) M.D. McReynolds, J.M. Dougherty and P.R. Hanson, Chem. Rev., 2004, 104, 2239-2258; (e) H. Kivela, Z. Zalan, P. Tähtinen, R. Sillanpaa, F. Fulop and K. Pihlaja, Eur. J. Org. Chem., 2005, 1189-1200 and references cited therein.         [ Links ]

6 C. McGuigan and P. Narashiman, Synthesis, 1993, 311-314.         [ Links ]

7 K.G. Devine, C. McGuigan, T.J. O'Connor, S.R. Nicholis and D. Kinchington, AIDS, 1990, 4, 371-373.         [ Links ]

8 P.J. Cox, Biochem. Pharmacol., 1979, 28, 2045-2049.         [ Links ]

9 M. Szekerke, Cancer Treatment Rept., 1976, 60, 347-354.         [ Links ]

10 L.C. Thomas, Interpretation of Infrared Spectra of Organophosphorus Compounds, Heyden & Sons, London, UK, 1974.         [ Links ]

11 (a) P.V.G. Reddy, P. Haranath, C.S. Reddy and C.N. Raju, Indian J. Chem., 2005, 44(B), 1437-1440; (b) Y.H. Babu, P.V.G. Reddy, C.S. Reddy, C.D. Reddy and P.U. Devi, J. Heterocycl. Chem., 2002, 39, 1039-1044; (c) A.U.R. Sankar, B.S. Kumar, M.V.N. Reddy, B. Haribabu and C.N. Raju, Arkivoc, 2007, 14, 300-308; (d) T.S. Cameron, R.E. Cordes, T Demir and R.A. Shaw, J. Chem. Soc., Perkin Trans. 1, 1979, 2896-2901.         [ Links ]

12 L.D. Quin and J.G. Verkade, Phosphorus-31 NMR Spectral Properties in Compound Characterization and Structural Analysis, VCH Publishers Inc, New York, NY, USA, 1994.         [ Links ]

13 A.W. Bauer, W.M. Kirby, J.C. Sherris and M. Truck, Am. J. Clin. Pathol., 1966, 45, 493-496.         [ Links ]

Received 8 September 2008
Revised 6 November 2008
Accepted 2 January 2009

* To whom correspondence should be addressed. E-mail: csrsvu@gmail.com