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Zhang et al.
1775
dilutions of the solution were prepared (64, 32, 16, 8, 4,
2, 1, 0.5, 0.25 and 0.125 μg mL-1). The bacterial cultures
(ca. 108 CFU mL-1) in Müller-Hinton medium were added
to the corresponding tubes. The plates were incubated at
35 °C for 12 h. Chloramphenicol and fluconazole were
used as reference agents. Suitable solvent control (DMSO),
positive growth control and standard drug control were also
run simultaneously. The MIC values of the compounds
were recorded as the lowest concentration of each chemical
compound in the tubes with no turbidity of inoculated
bacteria/fungus.
2. Vögtle, F.; Cyclophan-Chemie; BG Teubner: Stuttgart, Germany,
1990.
3. Chen, P.; Jäkle F.; J. Am. Chem. Soc. 2011, 133, 20142.
4. Werz, D. B.; Fischer, F. R.; Kornmayer, S. C.; Rominger, F.;
Gleiter, R.; J. Org. Chem. 2008, 73, 8021.
5. Jeppesen, J. O.; Nielsen, M. B.; Becher, J.; Chem. Rev. 2004,
104, 5115.
6. Srinivasan, M.; Sankararaman, S.; Hopf, H.; Dix, I; Jones, P. G.;
J. Org. Chem. 2001, 66, 4299.
7. Rajakumar, P.; Padmanabhan, R.; Tetrahedron Lett. 2010, 51,
1059.
8. Arunachalam, M.; Ravikumar, I.; Ghosh, P.; J. Org. Chem. 2008,
73, 9144.
Crystal structure X-ray data of 4g and 4h
9. Bruno, G.; Cafeo, G.; Kohnke, F. H.; Nicolò, F.; Tetrahedron
2007, 63, 10003.
All measurements of compounds 4g and 4h were made
on a Bruker Smart APEX II CCD diffractometer with
graphite monochromated Mo-Kα radiation. The data was
collected at a temperature of 296 K using the ω-2θ scan
technique. Crystallographic data for the structure analysis
of compounds 4g and 4h was deposited at the Cambridge
Crystallographic Data Centre, CCDC No. 846714 and
846711, respectively. 25
10. Morisaki, Y.; Ishida, T.; Chujo, Y.; Org. Lett. 2006, 8, 1029.
11. Morisaki, Y.; Chujo, Y.; Prog. Polym. Sci. 2008, 33, 346.
12. Rajakumar, P.; Abdul Rasheed, A. M.; Rabia, A. I.;
Chamundeeswari, D.; Bioorg. Med. Chem. Lett. 2006, 16, 6019.
13. Melaiye, A.; Sun, Z.; Hindi, K.; Milsted, A.; Ely, D.; Reneker,
D. H.; Tessier, C. A.; Youngs, W. J.; J. Am. Chem. Soc. 2005,
127, 2285.
14. Krafft, M. E.; Fu, Z.; Boñaga, L. V. R.; Tetrahedron Lett. 2001,
42, 1427.
Conclusions
15. Leng, X.;Yang, B.; Liu,Y.; Xie,Y.; Tong, J.; Z. Naturforsch., B:
Chem. Sci. 2011, 66B, 930.
Eight novel compounds (4a-4h) were synthesized. XRD
studies were carried out for compounds 4g and 4h, which
were further stabilized by H-bond stacking interaction. These
new compounds 4a-4h represent a novel class of compounds
that incorporate an 11-membered ring lactone type structure.
Some of the synthesized cyclophanes have low antibacterial
or antifungal activities, providing stimulus for further studies.
16. Guha, S.; Saha, S.; J. Am. Chem. Soc. 2010, 132, 17674.
17. Guo, C. C.; Li, K. L.; Tong, R. B.; Chen, L. Zhang, X. B.; Chin.
J. Org. Chem. 2005, 25, 308.
18. Lin, S. W.; Sun, Q.; Ge, Z. M.; Wang, X.; Ye, J.; Li, R. T.;
Bioorg. Med. Chem. Lett. 2011, 21, 940.
19. Lv, J.; Liu T. T.; Wang, Y. M.; Eur. J. Med. Chem. 2008, 43, 19.
20. Gao, M. Z.; Gao, G.; Xu, Z. L.; Zingaro, R.A.; Tetrahedron Lett.
2002, 43, 5001.
Supplementary Information
21. Gao, B.;Yang, B. Q.; Li, T.; Zhang B. L.; Synth. Commun. 2009,
39, 2973.
Supplementary data is available free of charge at
22. Abdel-Kader, M. S.; J. Braz. Chem. Soc. 2003, 14, 48.
23. Carrillo, R.; Martin, V. S.; López, M.; Martin, T.; Tetrahedron
2005, 61, 8177.
Acknowledgment
24. Cameron, L. M.; Fyles, T. M.; Hu, C. W.; J. Org. Chem. 2002,
67, 1548.
This work was financially supported by the National
Natural Science Foundation of China (Grant No. 21172178
P. R. China).
25. Cambridge Crystallographic Data Center (CCDC), 12 Union
Road, Cambridge CB2 1EZ, UK, deposit@ccdc.cam.ac.uk,
2012.
References
1. Cram, D. J.; Steinberg, H.; J. Am. Chem. Soc. 1951, 73, 5691.
Submitted: July 11, 2012
Published online: September 25, 2012