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Efficient synthesis routes for various phthalimido phosphor esters as antimicrobial agents in terms of structure–activity relationship

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Abstract

A series of phthalimido phosphor derivatives—α-amino-phosphonates, amidophosphonates, phosphonic acid diamides, and oxadiazaphospholes—were prepared by applying different types of phosphorus(III) reagents to 2-methoxy-1H-isoindole-1,3(2H)-dione and 2-anilino-1H-isoindole-1,3(2H)-dione. On the basis of bioassay results, some of the new phosphoryl imides could be considered as lead molecules to be modified in order to improve their antibiotic activity.

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References

  1. Williams DM, Harris VH (1994) In: Murphy PJ (ed) Organophosphorus reagents, a practical approach in chemistry, Chap. 9. Oxford University Press, New York, p 237

  2. Fest C, Schmidt KJ (1973) The chemistry of organophosphorus pesticides. Springer, Berlin

    Google Scholar 

  3. Boulos LS, El-Din NK (1993) Tetrahedron 49:3871

    Article  CAS  Google Scholar 

  4. Couture A, Deniau E, Grandclaudon P (1997) Tetrahedron 53:10313

    Article  CAS  Google Scholar 

  5. Mortier J, Fortineau AD, Vaultier M (1999) Phosphorus Sulfur Silicon Relat Elem 149:221

    Article  CAS  Google Scholar 

  6. Winstead MB, Heine HW (1955) J Am Chem Soc 77:1913

    Article  CAS  Google Scholar 

  7. Hargreaves MK, Pritchard JG, Dave HR (1970) Chem Rev 70:439

    Article  CAS  Google Scholar 

  8. Harpp DN, Orwig BA (1970) Tetrahedron Lett 2691

  9. Mackie RK (1979) In: Cadogen JIG (ed), Organophosphorus reagents in organic synthesis, 2nd edn, Chap. 8. Academic Press, London, p 351

  10. Laboratori Baldacci DPA (1984) Jpn Patent 59 46,268

  11. Chem Abstr (1984) 101:54922

  12. Valencia E, Weiss I, Firdous S, Freyer AJ, Shamma M, Urzús A, Fajardo V (1984) Tetrahedron 40:3957

    Article  CAS  Google Scholar 

  13. Priestap HA (1985) Phytochemistry 24:849

    Article  CAS  Google Scholar 

  14. Seyferth D, Marmor RS, Hilbert P (1971) J Org Chem 36:1379

    Article  Google Scholar 

  15. Gaydou E, Peiffer G, Guillemonat A, Traynard JC (1972) CR Acad Sci Ser IIc Chim 275:547

    CAS  Google Scholar 

  16. Chun YJ, Park JH, Oh GM, Hong SI, Kim YJ (1994) Synthesis 909

  17. Baraldi PG, Guarneri M, Moroder F, Pollini GP, Simoni D (1982) Synthesis 653

  18. Yamauchi K, Kinoshita M (1972) Bull Chem Soc Jpn 45:2528

    Article  CAS  Google Scholar 

  19. Brown J, Su SCK, Shafer JA (1966) J Am Chem Soc 88:4468

    Article  CAS  Google Scholar 

  20. Shaikhiev IG, Fridland SV, Mukhutdinova GM (1999) Russian J Gen Chem 69:557

    CAS  Google Scholar 

  21. Ramirez F, Mareeek JF, Okazaki H (1976) J Am Chem Soc 98:5310

    Article  CAS  Google Scholar 

  22. Ivanov BE, Krokhina SS, Chichkanova TV, Kosacheva EM (1985) Izv Akad Nauk SSSR, Ser Khim 1:173

    Google Scholar 

  23. Ohta T (1943) J Pharm Soc Jpn 63:239

    CAS  Google Scholar 

  24. Chattaway FD, Tesh W (1920) J Chem Soc Trans 117:711

    Article  CAS  Google Scholar 

  25. Sutter P, Weis CD (1978) Phosphorus Sulfur 6:325

    Google Scholar 

  26. Fieser M, Fieser LF (1974) Reagents for organic synthesis, vol 4. Wiley, New York, 542

  27. Silverstein RM, Webster FXW, Kiemle DJ (eds) (2005) Spectrometric identification of organic compounds, 7th edn. Wiley, New York

  28. Kalinowski HO, Berger S, Braun S (1984) 13C-NMR-Spektroskopie. Thieme-Verlag, Stuttgart

    Google Scholar 

  29. Huang TB, Zhang JL (1995) Phosphorus Sulfur Silicon Relat Elem 104:33

    Article  CAS  Google Scholar 

  30. Noureddine R, Khaled B, Mohamed LB (2004) Phosphorus Sulfur Silicon Relat Elem 179:1387

    Article  Google Scholar 

  31. Collins AH (1976) Microbiological Methods, 2nd edn. Butterworth, London

    Google Scholar 

  32. Khan ZK (1997) In: Proceedings of International Workshop UNIDO-CDRI, in vitro and in vivo screening techniques for bioactivity screening and evaluation, p 210

  33. Sounders BC, Stark BP (1958) Tetrahedron 4:197

    Article  Google Scholar 

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Acknowledgments

We are grateful to the National Central Lab of Toxicology, Cairo, Egypt.

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Authors and Affiliations

  1. Chemical Industries Division, National Research Centre, Dokki, 12622, Giza, Egypt

    Wafaa Mahmoud Abdou & Rizk E. Khidre

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  1. Wafaa Mahmoud Abdou
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  2. Rizk E. Khidre
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Correspondence to Wafaa Mahmoud Abdou.

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Abdou, W.M., Khidre, R.E. Efficient synthesis routes for various phthalimido phosphor esters as antimicrobial agents in terms of structure–activity relationship. Monatsh Chem 141, 219–228 (2010). https://doi.org/10.1007/s00706-009-0244-1

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  • DOI: https://doi.org/10.1007/s00706-009-0244-1

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