Studies on 1-O-acetylbritannilactone and its derivative, (2-O-butyloxime-3-phenyl)-propionyl-1-O-acetylbritannilactone ester

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 5, 2004, Pages 1101-1104

  Liu, Shouxin ^a,b   Liu, He ^a   Yan, Weiying ^a   Zhang, Li ^c   Bai, Naisheng ^c   Ho, Chi Tang ^c  

^a HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b XI'AN JIAOTONG UNIVERSITY   (China)

^c RUTGERS UNIVERSITY   (United States)

Author keywords

(2 O butyloxime 1 phenyl) propionic acid derivative; Cytotoxicity; Inula britannica; Sesquiterpene lactone; X ray crystal structures

Indexed keywords

(2 O BUTYLOXIME 3 PHENYL)PROPIONYL 1 O ACETYLBRITANNILACTONE ESTER; 1 O ACETYLBRITANNILACTONE; ESTER DERIVATIVE; LACTONE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL; LIVER CELL CARCINOMA; SPECTROSCOPY;

INULA; INULA BRITANNICA;

EID: 1242339561     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.12.078     Document Type: Article

References (22)

1. Jiangsu, New Medical College. Dictionary of Traditional Chinese Materia Medica; Shanghai People's Press, 1977; Vol. 2, p 2216.
2. Zhou B.N., Bai N.S., Lin L.Z., Cordell G.A. Phytochem. 34:1993;249.
3. Zhou B.N., Bai N.S., Lin L.Z., Cordell G.A. Phytochem. 36:1994;721.
4. Wang Q., Zhou B.N., Zhang R.W., Lin Y.Y., Lin L.Z., Gil R.R., Cordell G.A. Planta Med. 62:1996;166.
5. Shao Y., Bai N.S., Zhou B.N. Phytochem. 42:1996;783.
6. Cheng Y.H., Liu S.X., Bai N.S. Yingyong Huaxue. 17:2000;550.
7. Ho, C.-T.; Rafi, M.; DiPaola, R. S.; Rosen, R. T.; Ghai, G.; Bai, N. United States Patent Number: 6,627,623, 2003.
8. Park E.J., Kim J. Planta Med. 64:1998;752.
9. Pettit G.R., Herald C.L., Gust D., Herald D.L., Vanell L.D. J. Org. Chem. 43:1978;1092.
10. Pettit G.R., Herald C.L., Judd G.F., Bolliger G., Thayer P.S. J. Pharm. Sci. 64:1975;2023.
11. Pettit G.R., Herald C.L., Judd G.F., Bolliger G., Vanell L.D., Lehto E., Pase C.P. Lloydia. 41:1978;29.
12. Lee K.H., Kimura T., Haruna M., McPhail A.T., Onan K.D., Huang H.C. Phytochem. 16:1977;1068.
13. Hall I.H., Lee K.H., Starnes C.O., Eigebaly S.A., Ibuka T., Wu Y.S., Kimura T., Haruna M. J. Pharm. Sci. 67:1978;1235.
14. Hall I.H., Lee K.H., Williams W.L. Jr., Kimura T., Hirayama T. J. Pharm. Sci. 69:1980;294.
15. Feng X., Yuan Y.J., Wu J.C. Bioorg. Med. Chem. Lett. 12:2002;3301.
16. Deutsh H.M., Glinski J.A., Hernandez M., Haugwitz R.D., Narayanan V.L., Suffness M., Zalkow L.H. J. Med. Chem. 32:1989;788.
17. Zhao Z., Kingston D.G.I., Crosswell A.R. J. Natl. Prod. 54:1991;1607.
18. 2CO to yield product 6. It was previously characterized by elemental analysis, IR, MS and NMR.
19. Armarego W.L.F., Perrin D.D. Purification of Laboratory Chemicals. 4th ed. 1999;Butterworth-Heinemann, Oxford, UK.
20. -1 3029 (alkyl), 1767 (CO), 1734 (CO), 1663 (C=N), m/z 290, 272, 215, 202, 189 (100%), 143, 117, 91, 43.
21. 2) was 0.0837 (all data).
22. The in vitro cytotoxicity was evaluated using a system based on tetrazolium salt (MTT), which was reduced by living cells to yield a soluble formazan product that could be assayed colorimetrically.