SciELO - Scientific Electronic Library Online

vol.61 author indexsubject indexarticles search
Home Pagealphabetic serial listing  

Services on Demand



Related links

  • On index processCited by Google
  • On index processSimilars in Google


South African Journal of Chemistry

On-line version ISSN 1996-840X
Print version ISSN 0379-4350

S.Afr.j.chem. (Online) vol.61  Durban  2008




Synthesis and antimicrobial activity of new α-aminophosphonic acid esters



Sanapalli S. Reddy; A.U. Ravi Sankar; C. Naga Raju*; V. Koteswara Rao

Department of Chemistry, Sri Venkateswara University, Tirupati-517502, India




Synthesis of new a-aminophosphonic acid esters (3a-I) was accomplished by the reaction of equimolar quantities of phenyl ethyl glycine and various aryl aldehydes with diethyl/ dimethylphosphite in dry toluene at reflux temperature. All the structures of the newly synthesized a-aminophosphonic acid esters (3a-I) were established by elemental analysis, and IR, 1H, 13C, 31P NMR and mass spectral data. The antimicrobial and antifungal activities of these compounds were evaluated and they exhibited significant activity.

Keywords: Phenyl glycine ethyl ester, aryl aldehydes, diethyl/dimethylphosphite, antimicrobial activity



Full text available only in pdf format.



The authors express their thanks to Prof. C. Devendranath Reddy and Dr C. Suresh Reddy, Department of Chemistry, Sri Venkateswara University, Tirupati, India, for their encouragement and helpful discussion and the Directors, IISc, Bangalore, and CDRI, Lucknow, India, for the analytical and spectral data.



1 B. Kaboudin and R. Nazari, Tetrahedron Lett, 2001, 42, 8211-8213.         [ Links ]

2 S. Chandrasekhar, S.J. Prakash, V. Jagadeshwar and C. Narisimhulu, Tetrahedron Lett., 2001, 42, 5561-5563.         [ Links ]

3 J. Hiratake and J. Oda, Biosci. Biotechnol. Biochem, 1997, 61, 211-218.         [ Links ]

4 VP. Kukhar and H.R. Hudson, Eds., Aminophosphonic and Amino-phosphinic Acids, John Wiley & Sons, New York, USA, 2000.         [ Links ]

5 A.B. Smith III, K.M. Yager and C.M. Taylor, J. Am. Chem. Soc, 1995, 117, 10879-10888.         [ Links ]

6 R. Hirschmann, A.B. Smith III, C.M. Taylor, P.A. Benkovic, S.D. Taylor, K.M. Yager, P.A. Sprengler and S.J. Benkovic, Science, 1994, 265, 234-237.         [ Links ]

7 M.C. Allen, W. Fuhrer, B. Tuck, R. Wade and J.M. Wood, J. Med. Chem., 1989, 32, 1652-1661.         [ Links ]

8 F.R. Atherton, C.H. Hassall and R.W. Lambert, J. Med. Chem, 1986, 29, 29-40.         [ Links ]

9 (a) E. Alonso, E. Alonso, A. Solis and C. del Pozo, Synlett, 2000, 698-700; (b) X.J. Mu, M.Y. Lei, J.P. Zoua and W. Zhang, Tetrahedron Lett., 2006, 47, 1125-1127.         [ Links ]

10 L.C. Thomas, The Interpretation of the Infrared Spectra of Organo-phosphorus Compounds, Heyden & Sons Ltd., London, UK, 1974.         [ Links ]

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

12 (a) Z. Zhuang-Ping and L. Jun-Ping, Synth. Commun., 2005, 35, 2501-2508; (b) J.S. Yadav, B.V.S. Reddy, K.S. Raj, K.B. Reddy and A.R. Prasad, Synthesis, 2001, 15, 2277-2280; (c) H. Firouzabadi, N. Iranpoor and S. Sobhani, Synthesis, 2004, 16, 2692-2696.         [ Links ]

13 J.C. Vincent and H.W. Vincent, Proc. Soc. Expt. Biol. Med., 1944, 55, 162-164.         [ Links ]

14 H.J. Benson. Microbiological Applications, 5th edn., W.C. Brown Publications, Boston, MA, USA, 1990.         [ Links ]



Received 21 June 2008
Revised 1 August 2008
Accepted 1 October 2008



*To whom correspondence should be addressed. E-mail:

Creative Commons License All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License