Monatshefte für Chemie - Chemical Monthly

, Volume 141, Issue 1, pp 79–93

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

  • Paramasivam Parthiban
  • Paramasivam Rathika
  • Keun Soo Park
  • Yeon Tae Jeong
Original Paper

DOI: 10.1007/s00706-009-0221-8

Cite this article as:
Parthiban, P., Rathika, P., Park, K.S. et al. Monatsh Chem (2010) 141: 79. doi:10.1007/s00706-009-0221-8

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

Keywords

2,4-Diaryl-3-azabicyclo[3.3.1]nonan-9-one oximeO-MethyloximeN-Methylation2D NMRConformationAntifungal activity

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  • Paramasivam Parthiban
    • 1
  • Paramasivam Rathika
    • 2
  • Keun Soo Park
    • 1
  • Yeon Tae Jeong
    • 1
  1. 1.Division of Image Science and Information EngineeringPukyong National UniversityBusanRepublic of Korea
  2. 2.Department of MicrobiologyAnnamalai UniversityChidambaramIndia