Skip to main content
SpringerLink
Log in

Synthesis, complete NMR spectral assignments, and antifungal screening of new 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one oxime derivatives

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

Abstract

A series of differently substituted 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one oximes have been synthesized and their 1H and 13C NMR chemical shifts have been unambiguously assigned using H,H-COSY, NOESY, HSQC, and HMBC spectral data. On the basis of the NMR studies, irrespective of the nature and position of the substituents, all reported compounds exist in twin-chair conformation with equatorial disposition of the phenyl groups at C-2 and C-4 of the 3-azabicyclononane moiety. Among the synthesized oxime derivatives, compounds with halo-substituents at ortho/para positions of the phenyl showed good antifungal profile against all tested organisms.

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
Fig. 4

Similar content being viewed by others

References

  1. Jeyaraman R, Avila S (1981) Chem Rev 81:149

    Article  CAS  Google Scholar 

  2. Hardick DJ, Blagbrough IS, Cooper G, Potter BVL, Critchley T, Wonnacott S (1996) J Med Chem 39:4860

    Article  CAS  Google Scholar 

  3. Paterson D, Nordberg A (2000) Prog Neurobiol 61:75

    Article  CAS  Google Scholar 

  4. Bryant DL, Free RB, Thomasy SM, Lapinsky DJ, Ismail KA, McKay SB, Bergmeier SC, McKay DB (2002) Neurosci Res 42:57

    Article  CAS  Google Scholar 

  5. Barker D, Lin DH, Carland JE, Chu CP, Chebib M, Brimble MA, Savage GP, McLeod MD (2005) Bioorg Med Chem 13:4565

    Article  CAS  Google Scholar 

  6. Parthiban P, Aridoss G, Rathika P, Ramkumar V (2009) Bioorg Med Chem Lett 19:6981

    Google Scholar 

  7. Aridoss G, Balasubramanian S, Parthiban P, Kabilan S (2007) Spectrochim Acta Part A 68:1153

    Article  CAS  Google Scholar 

  8. Parthiban P, Balasubramanian S, Aridoss G, Kabilan S (2008) Spectrochim Acta Part A 70:11

    Article  CAS  Google Scholar 

  9. Parthiban P, Ramachandran R, Aridoss G, Kabilan S (2008) Magn Reson Chem 46:780

    Article  CAS  Google Scholar 

  10. Parthiban P, Rani M, Kabilan S (2009) Monatsh Chem 140:287

    Article  CAS  Google Scholar 

  11. Parthiban P, Aridoss G, Rathika P, Ramkumar V, Kabilan S (2009) Bioorg Med Chem Lett 19:2981

    Article  CAS  Google Scholar 

  12. Iriepa I, Madrid AI, Galvez E, Bellanato J (2003) J Mol Struct 651–653:579 and references cited therein

  13. Arias-Perez MS, Alejo A, Galvez E, Perez SM, Santos MJ (1995) J Mol Struct 349:169

    Article  CAS  Google Scholar 

  14. Arias MS, Smeyers YG, Fernandez MS, Smeyers NJ, Galvez E, Fonseca I, Aparicio JS (1994) J Org Chem 59:2565

    Article  CAS  Google Scholar 

  15. Goodall KJ, Brimble MA, Barker D (2006) Magn Reson Chem 44:980

    Article  CAS  Google Scholar 

  16. Polonski T, Pham M, Milewska MJ, Gdaneic M (1996) J Org Chem 61:3766

    Article  CAS  Google Scholar 

  17. Parthiban P, Ramkumar V, Kim MS, Lim KT, Jeong YT (2008) Acta Cryst E 64:1586

    Article  Google Scholar 

  18. Parthiban P, Thirumurugan K, Ramkumar V, Pazhamalai S, Jeong YT (2008) Acta Cryst E 64:1708

    Article  Google Scholar 

  19. Parthiban P, Ramkumar V, Santan HD, Kim JT, Jeong YT (2008) Acta Cryst E 64:1710

    Article  Google Scholar 

  20. Rameshkumar N, Veena A, Ilavarasan R, Adiraj M, Shanmugapandiyan P, Sridhar SK (2003) Biol Pharm Bull 26:188

    Article  CAS  Google Scholar 

  21. Balasubramanian S, Aridoss G, Parthiban P, Ramalingan C, Kabilan S (2006) Biol Pharm Bull 29:125

    Article  CAS  Google Scholar 

  22. Parthiban P, Balasubramanian S, Aridoss G, Kabilan S (2005) Med Chem Res 14:523

    Article  CAS  Google Scholar 

  23. Klod S, Koch A, Kleinpeter E (2002) J Chem Soc Perkin Trans 2:1506

    Google Scholar 

  24. Lambert JB, Netzel DA, Sun HN, Lilianstorm KK (1976) J Am Chem Soc 98:3778

    Article  CAS  Google Scholar 

  25. Gillespie SH (1994) Medical microbiology-illustrated. Butterworth–Heinemann, London, p 234

    Google Scholar 

Download references

Acknowledgments

This work was supported by Corporate-affiliated Research Institute of Academic-Industrial-Institutional Cooperation Improvement Business No. S7080008110.

Author information

Authors and Affiliations

  1. Division of Image Science and Information Engineering, Pukyong National University, Busan, 608-739, Republic of Korea

    Paramasivam Parthiban, Keun Soo Park & Yeon Tae Jeong

  2. Department of Microbiology, Annamalai University, Annamalainagar, Chidambaram, 608002, India

    Paramasivam Rathika

Authors
  1. Paramasivam Parthiban
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Paramasivam Rathika
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Keun Soo Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yeon Tae Jeong
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yeon Tae Jeong.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Parthiban, P., Rathika, P., Park, K.S. et al. Synthesis, complete NMR spectral assignments, and antifungal screening of new 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-one oxime derivatives. Monatsh Chem 141, 79–93 (2010). https://doi.org/10.1007/s00706-009-0221-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-009-0221-8

Keywords

Search

Navigation