Synthesis and biological evaluation of antitumour-active betulin derivatives

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 3, 2010, Pages 1344-1355

  Csuk, René ^a   Barthel, Alexander ^a   Kluge, Ralph ^a   Ströhl, Dieter ^a   Kommera, Harish ^b   Paschke, Reinhard ^b  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b BioSolutions GmbH   (Germany)

Author keywords

Antitumour activity; Apoptosis; Betulin; Betulinic acid

Indexed keywords

2 ([3BETA ACETOXY 28 NORLUP 20(29) EN 17BETA YL] 3 OXOMETHYL) GAMMA BUTYROLACTONE; 2 ([3BETA ACETOXY 28 NORLUP 20(29) EN 17BETA YL]HYDROXYMETHYL) GAMMA BUTYROLACTONE; 2 [3BETA ACETOXY 28 NORLUP 20(29) EN 17BETA YL] 1,5 DIOXA SPIRO[2.4]HEPTAN 4 ONE; 2 [3BETA ACETOXY 28 NORLUP 20(29) EN 17BETA YL]HYDROXYMETHYL) GAMMA BUTYRO LACTONE; 3 [3BETA ACETOXY 28 NORLUP 20(29) EN 17BETA YL] OXIRANE 2 CARBONITRIL; 3 [3BETA ACETOXY 28 NORLUP 20(29) EN 17BETA YL] OXIRANE 2 CARBOXYLIC ACID DIETHYLAMIDE; 3 [3BETA ACETOXY 28 NORLUP 20(29) EN 17BETA YL] OXIRANE 2 CARBOXYLIC ACID METHYL ESTER; 3 ACETYL 28 (2 ETHOXY 2 OXOETHYL)ALLOBETULIN; 3 ACETYL 28 (4 ETHOXY 2,4 DIOXOBUT 1 YL)ALLOBETULIN; 3BETA HYDROXY 17BETA [2 OXIRANYL] 28 NORLUP 20(29) EN; 4 ([3EBETA ACETOXY 28 NORLUP 20(29) EN 17BETA YL]HYDROXYMETHYL) 2 BUTEN 4 OLIDE; BETULIC ACID; BETULIN; CARBONYL DERIVATIVE; EPOXIDE; ETHYL 3 [3BETA ACETOXY 28 NORLUP 20(29) EN 17BETA YL] 3 HYDROXYPROPIONATE; ETHYL 3 [3BETA ACETOXY 28 NORLUP 20(29) EN 17BETA YL] 3 OXO PROPIONATE; ETHYL 3 [3BETA ACETOXY 28 NORLUP 20(29) EN 17BETA YL]ACRYLATE; ETHYL 3 [3BETA METHOXY 28 NORLUP 20(29) EN 17BETA YL] 3 HYDROXY PROPIONATE; ETHYL 3 [3BETA METHOXY 28 NORLUP 20(29) EN 17BETA YL] 3 OXO PROPIONATE; ETHYL 3 [3BETA METHOXY 28 NORLUP 20(29) EN 17BETA YL]ACRYLATE; ETHYL 5 [3BETA ACETOXY 28 NORLUP 20(29) EN 17BETA YL] 5 HYDROXY 3 OXO VALERATE; ETHYL 5 [3BETA METHOXY 28 NORLUP 20(29) EN 17BETA YL] 5 HYDROXY 3 OXO VALERATE; GLYCIDOL; NUCLEOPHILE; SULFORHODAMINE B; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CANCER CELL CULTURE; COLORIMETRY; CYTOTOXICITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP; TRITERPENES;

EID: 75449104167     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.12.024     Document Type: Article

References (26)

1. Fujioka T., Kashiwada Y., Kilkuskie R.E., Cosentino L.M., Ballas L.M., Jiang J.B., Janzen W.P., Chen I.S., and Lee K.H. J. Nat. Prod. 57 (1994) 243
2. Zhou J., Chen C.H., and Aiken C. Retrovirology 1 (2004) 15
3. Li F., Goila-gaur R., Salzwedel K., Kilgore N.R., Reddick M., Matallana C., Castillo A., Zoumplis D., Martin D.E., Orenstein J.M., Allaway G.P., Freed E.O., and Wild C.T. Proc. Natl. Acad. Sci. U.S.A. 100 (2003) 13555
4. Mayaux J.F., Bousseau A., Pauwels R., Huet T., Henin Y., Dereu N., Evers M., Soler F., and Poujade C. Proc. Natl. Acad. Sci. U.S.A. 91 (1994) 3564
5. Labrosse B., Treboute C., and Alizon M. J. Virol. 74 (2000) 2142
6. Pisha E., Chai H., Lee I.S., Chagwedera T.E., Farnsworth N.R., Cordell G.A., Beecher C.W.W., Fong H.H.S., and Kinghorn A.D. Nat. Med. (NY) 1 (1995) 1046
7. Fulda S., Scaffidi C., Susin S.A., Krammer P.H., Kroemer G., Peter M.E., and Debatin K.M. J. Biol. Chem. 273 (1998) 33942
8. Fulda S., and Debatin K.M. Med. Pediatr. Oncol. 35 (2000) 616
9. Wick W., Grimmel C., Wagenknecht B., Dichgans J., and Weller M. J. Pharmacol. Exp. Ther. 289 (1999) 1306
10. Tan Y., Yu R., and Pezzuto J.M. Clin. Cancer Res. 9 (2003) 2866
11. Barthel A., Stark S., and Csuk R. Tetrahedron 64 (2008) 9225
12. Komissarova N.G., Belenkova N.G., Spirikhin L.V., Shitikova O.V., and Yunusov M.S. Chem. Nat. Compd. 38 (2002) 58
13. Ballester M. Chem. Rev. 55 (1955) 283
14. Li A.-H., Dai L.-X., and Aggarwal V.K. Chem. Rev. 97 (1997) 2341
15. Bessodes M., Egron M.-J., and Antonakis K. J. Chem. Soc., Perkin Trans. 1 (1989) 2099
16. Dede R., Michaelis L., Fuentes D., Yawer M.A., Hussein I., Fischer C., and Langer P. Tetrahedron 63 (2007) 12547
17. Vong B.H., Kim S.H., Abraham S., and Theodorakis E.A. Angew. Chem., Int. Ed. 43 (2004) 3947
18. Ahmad N.M. In: Li J.J., and Corey E.J. (Eds). Name Reactions for Functional Group Transformations (2007), John Wiley & Sons, Hoboken 291-308
19. Eles J., Kalaus G., Greiner I., Kajtar-Peredy M., Szabo P., Keseru G.M., Szabo L., and Szantay C. J. Org. Chem. 67 (2002) 7255
20. Carnell A.J., Head R., Bassett D., and Schneider M. Tetrahedron: Asymmetry 15 (2004) 821
21. Li T.-S., Wang J.-X., and Zheng X.-J. J. Chem. Soc., Perkin Trans. 1 (1998) 3957
22. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenney S., and Boyd M.R. J. Natl. Cancer Inst. 82 (1990) 1107
23. Kim D.S.H.L., Pezzuto J.M., and Pisha E. Bioorg. Med. Chem. Lett. 8 (1998) 1707
24. You Y.J., Kim Y., Nam N.-H., and Ahn B.-Z. Bioorg. Med. Chem. Lett. 13 (2003) 3137
25. Gong J.P., Traganos F., and Darzynkiewicz Z. Anal. Biochem. 218 (1994) 314
26. Katsarou M.E., Efthimiadou E.K., Psomas G., Karaliota A., and Vourloumis D. J. Med. Chem. 51 (2008) 470