Notes

Synthesis and Antibacterial Activity of 1-(Coumarin-3-carbonyl)guaiazulene Derivatives

  • Wang Daolin ,
  • Dong Zhe ,
  • Xu Jiao ,
  • Li Di
Expand
  • a Key Laboratory of Synthesis & Application of Functional Compound, College of Chemistry, Chemical Engineering & Food Safety, Bohai University, Jinzhou 121003;
    b Cosmetology Department, Heilongjiang University of Chinese Medicine,Jiamusi Institute, Jiamusi, 154007

Online published: 2013-03-07

Supported by

Project supported by the Science and Technology Department of Liaoning Province (No.2011220022), and the Innovation Talent Program of Heilongjiang University of Chinese Medicine.

Abstract

An efficient and easy method for the synthesis of 1-(coumarin-3-carbonyl)guaiazulene derivatives by the condensation of 1-cyanoacetylguaiazulene and 2-hydroxyaldehydes in the presence of ammonium acetate has been described. The structures of all target compounds have been confirmed by NMR, IR, MS spectra and elemental analysis, and the bioassay result indicated that some of the title compounds had relatively antibacterial activity.

Cite this article

Wang Daolin , Dong Zhe , Xu Jiao , Li Di . Synthesis and Antibacterial Activity of 1-(Coumarin-3-carbonyl)guaiazulene Derivatives[J]. Chinese Journal of Organic Chemistry, 0 , (0) : 0 -0 . DOI: 10.6023/cjoc201301025

References

[1] Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.

[2] (a) Geen, G. R.; Evans, J. M.; Vong, A. K. In Comprehensive Heterocyclic Chemistry II; Pergamon: Oxford, 1984, 5, 469.

(b) Sardari, S.; Mori, Y.; Horita, K.; Micetich, R.; Nishibe, G.; Daneshtalab, S. M. Bioorg. Med. Chem. 1999, 7, 1933.

[3] Sreenivasulu, B.; Sundaramurthy, V.; Rao, N. V. S. Proc. Ind. Acad. Sci., Sec. A. 1974, 79, 41.

[4] Hermodosn H.; Barker W.; Med. Chem. 1971, 14, 167.

[5] Romine, K. R.; Morris, J. K.; Howe, W. J.; Tomich, P. K.; Horng, M. M.; Chong, K. T.; Hinshaw, R. R.; Anderson, D. J.; Strohbach, J. W.; Turner, S. R.; Mizsak, S. A. J. Med. Chem. 1996, 39, 4125.

[6] (a) Audisio, D.; Messaoudi, S.; Brion, J.-D.; Alami, M. Eur. J. Org. Chem. 2010, 6, 1046.

(b) Khan, A. T.; Das, D. K. Tetrahedron Lett. 2012, 53, 2345.

[7] Yanagisawa, T.; Wakabayashi, S.; Tomiyama, T.; Yasunami, M.; Takase, K. Chem. Pharm. Bull. 1988, 36, 641.

[8] (a) Asato, A. E.; Peng, A.; Hossain, M. Z.; Mirzadegan, T.; Bertram, J. J. Med. Chem. 1993, 36, 3137.

(b) Hong, B. C.; Jiang, Y. F.; Kumar, E. S. Bioorg. Med. Chem. Lett. 2001, 11, 1981.

[9] Becker, D. A.; Ley, J. J.; Echegoyen, L.; Alvarado, R. J. Am. Chem. Soc. 2002, 124, 4678.

[10] (a) Fisher, G. Advances in Heterocyclic Chemistry Ed.: Katritzky, A. R., Academic Press, New York, 1995, 64, p. 81.

(b) Fisher, G. Advances in Heterocyclic Chemistry Ed.: by Katritzky, A. R., Academic Press, New York, 1996, 66, p. 285.

[11] (a) Wang, D.-L.; Xu, J.; Han, S.; Gu, Z. Chin. J. Org. Chem. 2007, 27, 1305 (in Chinese). (王道林, 徐姣, 韩珊, 谷峥, 有机化学, 2007, 27, 1305.)

(b) Imafuku, K.; Wang, D. -L. Heterocycles 2002, 58, 405.

(c) Wang, D.-L.; Imafuku, K. Heterocycles 2001, 54, 647.

[12] (a) Wang, D.-L.; Xu, J.; Gu, Z.; Han, S. Chin. J. Org. Chem. 2007, 27, 1404 (in Chinese). (王道林, 徐姣, 谷峥, 韩珊, 有机化学, 2007, 27, 1404.)

(b) Wang, D.-L.; Den, J. J.; Xu, J.; Gu, Z.; Han, S. Imafuku. K. Heterocycles 2007, 71, 2237.

(c) Wang, D.-L.; Imafuku. K. J. Heterocycl. Chem. 2004, 41, 723.

[13] Wang, D.-L.; Han, S.; Gu, Z.; Xu, J. Chin. J. Org. Chem. 2008, 28, 1641 (in Chinese). (王道林, 韩珊, 谷峥, 徐姣, 有机化学, 2008, 28, 1641.)

[14] (a) Sun, S. -G.; Gu, Z.; Wang, D. -L.; Han, S.; Huang, X. -D. Chin. J. Org. Chem. 2009, 29, 2012 (in Chinese). (孙曙光, 谷峥, 王道林, 韩珊, 黄孝东, 有机化学, 2009, 29, 2012.)

(b) Wang, D.-L.; Lin, L.-N.; Li, S.-F.; Li. W.; Li, Y.-F. Chin. J. Org. Chem. 2010, 30, 1774 (in Chinese). (王道林, 林力男, 李少飞, 李伟, 李元峰, 有机化学, 2010, 30, 1774.)

[15] (a) Janistyn, H. Deut. Apoth. -Ztg.1951, 91, 319.

(b) Wolfaramm. C. Pharmazie 1952, 7, 604.

(c) Asato, A. E.; Li, X. Y.; Mead, D.; Patterson, G. M. L.; Liu, R. S. H. J. Am. Chem. Soc. 1990, 112, 7398.

[16] Wang, D.-L.; Li, D.; Cao, L. Chin. J. Org. Chem. 2012, 32, 1741 (in Chinese). (王道林, 李帝, 曹亮, 有机化学, 2012, 32, 1741.)

[17] (a) Al-Matar, H. M.; Adam, A. Y.; Khalil, K. D.; Elnagd, M. H. Arkivoc 2012, (vi), 1.

(b) Shiri, M.; Zolfigol, M. A.; Pirveysian, M.; Ayazi-Nasrabadi, R.; Kruger, H. G.; Naicker, T.; Mohammadpoor- Baltork, I. Tetrahedron 2012, 68, 6059.

(c) Huang, Z. -b.; Hu, Y.; Zhou, Y.; Shi, D. -Q. ACS Comb. Sci. 2011, 13, 45.

[18] (a) Areias, F.; Costa, M.; Casteo, M.; Brea, J.; Gregori-Puigjane, E.; Proenca, M. F.; Mestres, J.; Loza, M. Eur. J. Med. Chem. 2012, 54, 303.

(b) Shams, H. Z.; Mohareb, R. M.; Helal, M. H.; Mahmoud, A. E. Molecules 2011, 16, 52.

[19] Xu, S.-Y.; Bian, R.-L.; Chen, X. Methodology of Pharmacology Experiments, People’s Medical Publishing House, Beijing, 1994, p. 1356 (in Chinese). (许淑云, 卞如濂, 陈修, 药理实验方法学, 人民卫生出版社, 北京, 1994, p. 1356.)

Outlines

/