Skip to main content

Advertisement

SpringerLink
Log in

Structural and Antimicrobial Activity Analyses of Different Forms of Sulfur-Nitrogen Containing Heterocyclic Supramolecule

  • Original Paper
  • Published:
Journal of Chemical Crystallography Aims and scope Submit manuscript

Abstract

Direct crystallization of sulfur-nitrogen containing heterocyclic supramolecule I from acetic acid (solvent free) or in presence of an inert solvent afforded the proton-transfer compound III. The presence of nitrogen and sulfur atoms enhanced the solid-state packing of III to adopt interesting supramolecular interactions such as; S···H, S···N, N···O, O···H, S···H. Compounds I and III inhibited the growth of the Gram positive bacteria, B. subtilis and M. luteus.

Graphical Abstract

The supramolecularity of sulfur-nitrogen containing heterocyclic supramolecule I which crystallized from acetic acid in presence of an inert solvent has been investigated and afforded the proton-transfer compound III. In addition, the antimicrobial activity of compounds I and III has been examined and revealed that both compounds inhibited the growth of the Gram positive bacteria, B. subtilis and M. luteus. Part of compound III crystal structure showing only the cationic fragment. Heteroatoms were only labeled for clarity.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Balasubramanian M, Keay JG (1996) In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II, vol 5. Pergamon Press, Oxford, p 245

    Chapter  Google Scholar 

  2. Bilker O, Lindo V, Panico M, Etiene AE, Paxton T, Dell A, Rogers M, Sinden RE, Morris HR (1998) Nature 392:289

    Article  Google Scholar 

  3. Charris J, Martinez P, Dominguez J, Lopez S, Angel J, Espinoza G (2003) Heterocycl Commun 9:251

    Article  CAS  Google Scholar 

  4. Chen YL, Fang KC, Sheu JY, Hsu SL, Tzeng CC (2001) J Med Chem 44:2374

    Article  CAS  Google Scholar 

  5. Doube D, Bloun M, Brideau C, Chan C, Desmarais S, Eithier D, Falgueyeret JP, Friesen RW, Girad M, Girad Y, Guay J, Tagari P, Yong RN (1998) Bioorg Med Chem Lett 8:1255

    Article  Google Scholar 

  6. Franck X, Fournet A, Prina E, Mahieux R, Hocquemiller R, Figadere B (2004) Bioorg Med Chem Lett 14:3635

    Article  CAS  Google Scholar 

  7. Hu B, Collini M, Unwalla R (2006) J Med Chem 49:6151

    Article  CAS  Google Scholar 

  8. Michael JP (1997) Nat Prod Rep 14:605

    Article  CAS  Google Scholar 

  9. Musiol R, Jampilek J, Buchta V, Silva L, Niedbala H, Bodeszwa B, Palka A, Majerz-Maniecka K, Oleksyn B, Polanski J (2006) Bioorg Med Chem 14:3592

    Article  CAS  Google Scholar 

  10. Roma G, Braccio MD, Grossi G, Chia M (2000) Eur J Med Chem 35:1021

    Article  CAS  Google Scholar 

  11. Saeed A, Elhadi S (2011) Synth Commun 41:1435

    Article  CAS  Google Scholar 

  12. Tempone AG, daSilva ACMP, Brandt CA, Martinez FS, Borborema SET, da Silveira MAB, de Andrade HF (2005) Antimicrob Agents Chemother 49:1076

    Article  CAS  Google Scholar 

  13. Tsotinis A, Vlachou M, Zouroudis S, Jeney A, Timar F, Thurston DE, Roussakis C (2005) Lett Drug Des Discov 2:189

    Article  CAS  Google Scholar 

  14. Vangapamdu S, Jain M, Jain R, Kaur S, Singh PP (2004) Bioorg Med Chem 12:2501

    Article  Google Scholar 

  15. Geng X, Li S, Bian X, Xie Z, Wang C (2008) ARKIVOC xiv:50

    Google Scholar 

  16. Alshahateet SF (2010) Mol Cryst Liq Cryst 533:152

    Article  CAS  Google Scholar 

  17. Alshahateet SF (2011) J Chem Crystallogr 41:276

    Article  CAS  Google Scholar 

  18. Alshahateet SF, Bishop R, Craig DC, Kooli F, Scudder ML (2008) Cryst Eng Comm 10(3):297

    CAS  Google Scholar 

  19. Alshahateet SF, Bishop R, Craig DC, Scudder ML (2003) Cryst Eng Comm 5:417

    CAS  Google Scholar 

  20. Alshahateet SF, Bishop R, Scudder ML, Hu CY, Lau EHE, Kooli F, Judeh ZMA, Chow PS, Tan RBH (2005) Cryst Eng Comm 7:139

    CAS  Google Scholar 

  21. Alshahateet SF, Ong TT, Bishop R, Kooli F, Messali M (2006) Cryst Growth Des 6(7):1676

    Article  CAS  Google Scholar 

  22. Kooli F, Hian PC, Weirong Q, Alshahateet SF, Chen F (2006) J Porous Mater 13(3):319

    Article  CAS  Google Scholar 

  23. Kooli F, Mianhui L, Alshahateet SF, Chen F, Yinghuai Z (2006) J Phys Chem Solids 67(5):926

    Article  CAS  Google Scholar 

  24. Zaghal MH, Qaseer HA, El-qisairi AK, Alshahateet SF, Shatnawi MY, Dawe LN (2009) J Chem Crystallogr 39(8):564

    Article  CAS  Google Scholar 

  25. A preliminary account of the crystal structure of III (CCDC 691695) has been published: Alghezawi NM, Alshahateet SF, Bishop R (2010) JJC 5(3):211

  26. Abu-Shanab B, Adwan G, Abu-Safiya D, Jarrar N, Adwan K (2004) Turk J Biol 28:99

    Google Scholar 

  27. Bishop R (1992) Org Synth 70:120

    CAS  Google Scholar 

  28. Bishosp R (1998) Org Synth IX:692

    Google Scholar 

  29. Cheng C–C, Yang C-J (1982) Org React 28:37

    CAS  Google Scholar 

  30. Alshahateet SF (2011) JJC 6(1):21

    CAS  Google Scholar 

  31. Alshahateet SF (2011) J Chem Crystallogr 41:570

    Article  CAS  Google Scholar 

  32. Sekhon BS (2009) Ars Pharm 50(3):99

    Google Scholar 

  33. Whitesides GM, Wong AP (2006) MRS Bull 31:19

    Article  CAS  Google Scholar 

  34. Corlette EM, Tieknik ERT (2009) J Chem Crystallogr 39:603

    Article  CAS  Google Scholar 

  35. Smith G, Wermuth UD, Sagatys DS (2011) J Chem Crystallogr 41:17

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors would like to thank Mutah University for support needed to conduct this work. Special thanks to Dr. Zaher Judeh (Nanyang Technological University, Singapore) for his technical help and valuable comments.

Author information

Authors and Affiliations

  1. Department of Chemistry, Mutah University, Mutah, Karak, 61710, Jordan

    Solhe F. Alshahateet & Nawash M. Alghezawi

  2. Department of Biological Sciences, Mutah University, Mutah, Karak, 61710, Jordan

    Wael A. Al-Zereini

Authors
  1. Solhe F. Alshahateet
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Wael A. Al-Zereini
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Nawash M. Alghezawi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Solhe F. Alshahateet.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Alshahateet, S.F., Al-Zereini, W.A. & Alghezawi, N.M. Structural and Antimicrobial Activity Analyses of Different Forms of Sulfur-Nitrogen Containing Heterocyclic Supramolecule. J Chem Crystallogr 41, 1807–1811 (2011). https://doi.org/10.1007/s10870-011-0176-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10870-011-0176-6

Keywords

Search

Navigation