Skip to main content
SpringerLink
Log in

Synthesis, spectroscopic characterization, crystal structures, theoretical studies, and antibacterial evaluation of two novel N-phosphinyl ureas

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Two novel N-phosphinyl ureas containing different substituents were synthesized and characterized by 1H, 13C, and 31P NMR, IR, UV, mass spectroscopy, and elemental analysis. The crystal structures of these compounds were determined by X-ray crystallography. The structure of one compound exhibits the presence of two independent forms of the molecule with equal occupancy in the lattice and theoretical data reveal the same stabilization energies for these conformers. The title molecules have anti conformation with respect to the C=O and P=O bonds, whereas the other compound shows syn configuration. Quantum chemical calculations were applied to clarify this conformational behavior. Furthermore, the molecular geometry and vibrational frequencies of the new derivatives in the ground state were calculated by using the Hartree–Fock (HF) and density functional method (B3LYP) with 6-31+G** and 6-311+G** basis sets and compared with experimental values. The new derivatives were additionally tested in view of their antibacterial properties.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Li HQ, Lv PC, Yan T, Zhu HL (2009) Anticancer Agents Med Chem 9:471

    CAS  Google Scholar 

  2. Seth PP, Ranken R, Robinson DE, Osgood SA, Risen LM, Rodgers EL, Migawa MT, Jefferson EA, Swayze EE (2004) Bioorg Med Chem Lett 14:5569

    Article  CAS  Google Scholar 

  3. Struga M, Kossakowski J, Kedzierska E, Fidecka S, Stefańska J (2007) Chem Pharm Bull 55:796

    Article  CAS  Google Scholar 

  4. Vishnyakova TP, Golubeva IA, Glebova EV (1985) Russ Chem Rev 54:249

    Article  Google Scholar 

  5. Zalán Z, Martinek TA, Lázár L, Fülöp F (2003) Tetrahedron 59:9117

    Article  Google Scholar 

  6. Billman JH, Meisenheimer JL, Awl RA (1964) J Med Chem 7:366

    Article  CAS  Google Scholar 

  7. Gholivand K, Shariatinia Z, Afshar F, Faramarzpour H, Yaghmaian F (2007) Main Group Chem 6:231

    Article  CAS  Google Scholar 

  8. Frank É, Kazi B, Mucsi Z, Ludányi K, Keglevich G (2007) Steroids 72:446

    Article  CAS  Google Scholar 

  9. Safiulina AM, Goryunov EI, Letyushov AA, Goryunova IB, Smirnova SA, Ginzburg AG, Tananaev IG, Nifant’ev EE, Myasoedov BF (2009) Mendeleev Commun 19:263

    Article  CAS  Google Scholar 

  10. Goryunov EI, Nifant’ev EE, Myasoedov BF (2007) RF Patent 2 296 768

  11. Khailova NA, Krepysheva NE, Saakyan GM, Bagautdinova RKh, Shaimardanova AA, Zyablikova TA, Azancheev NM, Litvinov IA, Gubaidullin AT, Zverev VV, Pudovik MA, Pudovik AN (2002) Russ J Gen Chem 72:1071

    Article  CAS  Google Scholar 

  12. Papanastassiou ZB, Bardos TJ (1962) J Med Chem 5:1000

    Article  CAS  Google Scholar 

  13. Zhao GF, Yang HZ, Wang LX (1998) Chem J Chin Univ 19:555

    CAS  Google Scholar 

  14. Tananaev IG, Letyushov AA, Safiulina AM, Goryunova IB, Baulina TV, Morgalyuk VP, Goryunov EI, Gribov LA, Nifant’ev EE, Myasoedov BF (2008) Dokl Chem 422:260

    Article  CAS  Google Scholar 

  15. Gholivand K, Mostaanzadeh H, Koval T, Dusek M, Erben MF, Della Ve′dova CO (2009) Acta Cryst B 65:502

    Article  Google Scholar 

  16. Gholivand K, Pourayoubi M (2004) Z Anorg Allg Chem 630:1330

    Article  CAS  Google Scholar 

  17. Gholivand K, Shariatinia Z, Pourayoubi M (2006) Z Anorg Allg Chem 632:160

    Article  CAS  Google Scholar 

  18. Gholivand K, Pourayoubi M, Shariatinia Z, Mostaanzadeh H (2005) Polyhedron 24:655

    Article  CAS  Google Scholar 

  19. Gholivand K, Madani Alizadehgan A, Mojahed F, Soleimani P (2008) Polyhedron 27:1639

    Article  CAS  Google Scholar 

  20. Gholivand K, Shariatinia Z, Ansar S, Mashhadi SM, Daeepour F (2009) Struct Chem 20:481

    Article  CAS  Google Scholar 

  21. Gholivand K, Mostaanzadeh H, Koval T, Dusek M, Erben MF, Stoeckli-Evans H, Della Ve′dova CO (2010) Acta Cryst B 66:441

    Article  Google Scholar 

  22. Kirsanov AV (1954) J Gen Chem USSR 24:1031

    CAS  Google Scholar 

  23. Kirsanov AV, Zhmurova IV (1956) J Gen Chem USSR 26:2642

    CAS  Google Scholar 

  24. Eliel E, Hutchins RO (1969) J Am Chem Soc 91:2703

    Article  CAS  Google Scholar 

  25. Cogridge DEC (1995) Phosphorus, an outline of its chemistry, biochemistry, and technology, 5th edn. Elsevier, Amsterdam

    Google Scholar 

  26. Bentrude WG, Setzer WN, Khan M, Sopchik AE, Ramli E (1991) J Org Chem 56:6127

    Article  CAS  Google Scholar 

  27. Gholivand K, Pourayoubi M, Shariatinia Z (2007) Polyhedron 26:837

    Article  CAS  Google Scholar 

  28. Gholivand K, Hosseini Z, Pourayoubi M, Shariatinia Z (2005) Z Anorg Allg Chem 631:3074

    Article  CAS  Google Scholar 

  29. Gholivand K, Shariatinia Z (2007) Struct Chem 18:95

    Article  CAS  Google Scholar 

  30. Iriarte AG, Erben MF, Gholivand K, Jios JL, Ulic SE, Della Ve′dova CO (2008) J Mol Struct 886:66

    Article  CAS  Google Scholar 

  31. Iriarte AG, Cutin EH, Erben MF, Ulic SE, Jios JL, Della Ve′dova CO (2008) Vib Spectrosc 46:107

    Article  CAS  Google Scholar 

  32. Mizushima S (1954) Structure of molecules and internal rotation. Academic, New York

    Google Scholar 

  33. Watanabe IM, Mizuchima M, Masiko Y (1943) Sci Pap Inst Phys Chem Res Jpn 40:425

    CAS  Google Scholar 

  34. Badawi HM (2009) Spectrochim Acta A 72:523

    Article  Google Scholar 

  35. Mido Y, Kitagawa I, Hashimoto M, Matsuura H (1999) Spectrochim Acta A 55:2623

    Article  Google Scholar 

  36. Gholivand K, Madani Alizadehgan A, Arshadi S, Anaraki Firooz A (2006) J Mol Struct 791:193

    Article  CAS  Google Scholar 

  37. Sheldrick GM (1998) SHELXTL V.5.10, Structure Determination Software Suite, Bruker AXS. Madison, WI

    Google Scholar 

  38. Sheldrick GM (1998) SADABS V. 2.01, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS. Madison, WI

    Google Scholar 

  39. Greenwood D (1989) Antimicrobial chemotherapy. Oxford University Press, New York

    Google Scholar 

  40. Vincent JG, Vincent HW (1994) Proc Soc Exp Biol Med 55:162

    Google Scholar 

  41. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Zakrzewsky VG, Montgomery JA Jr, Stratman RE, Burant JC, Dapprich S, Millam JM, Daniels AD, Kudin KN, Strain MC, Farkas O, Tomasi J, Barone V, Cossi M, Cammi R, Menucci B, Pomelli C, Adamo C, Clifford S, Ochterski J, Petersson GA, Ayala PY, Cui Q, Morokuma K, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Cioslovski J, Ortiz JV, Baboul AG, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Gomperts R, Martin RI, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Andres JL, Gonzales C, Head-Gordon M, Replogle ES, Pople JA (1998) Gaussian 98, Revision A.6. Gaussian, Pittsburgh

    Google Scholar 

Download references

Acknowledgments

The financial support of this work by the Research Council of Tarbiat Modares University is gratefully acknowledged.

Author information

Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, P.O. Box 14115-175, Tehran, Iran

    Khodayar Gholivand & Nilufar Dorosti

Authors
  1. Khodayar Gholivand
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nilufar Dorosti
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Khodayar Gholivand.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 1369 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gholivand, K., Dorosti, N. Synthesis, spectroscopic characterization, crystal structures, theoretical studies, and antibacterial evaluation of two novel N-phosphinyl ureas. Monatsh Chem 142, 183–192 (2011). https://doi.org/10.1007/s00706-010-0436-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-010-0436-8

Keywords

Search

Navigation