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Synthesis 2005(7): 1157-1163
DOI: 10.1055/s-2005-861861
DOI: 10.1055/s-2005-861861
PAPER
© Georg Thieme Verlag Stuttgart · New York
Fluorination of Betulinines and Other Triterpenoids with DAST
Further Information
Received
1 September 2004
Publication Date:
10 March 2005 (online)
Publication History
Publication Date:
10 March 2005 (online)
Abstract
Betulinines are lupane, des-E-lupane, 18-lupene, 20(29)-lupene and 18α-oleanane derivatives with antitumor activity. We examined fluorination of these derivatives using diethylaminosulfur trifluoride (DAST) as fluorinating agent. We prepared 19β,28-epoxy-2,2-difluoro-18α-oleanan-3-one (3c), 19β,28-epoxy-2,2-difluoro-18α-oleanan-3β-ol (4a), methyl 3β-acetoxy-30-fluorolup-20(29)-ene-28-oate (6b), 3β,28-diacetoxy-22-oxo-21,21-difluorolup-18-ene (8b) and several other fluorinated betulinines for in vitro cytotoxicity tests which failed to demonstrate significant anticancer activity so far.
Key words
antitumor agents - fluorine - rearrangements - steric hindrance - terpenoids
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Hudlicky M. Org. React. 1988, 35: 513 - 2
Slavikova B.Kasal A.Chodounska H.Kristofikova Z. Collect. Czech. Chem. Commun. 2002, 67: 30 - 3
Kirihara M. Yakugaku Zasshi 2000, 120: 339 ; Chem. Abstr. 2000, 132, 347199 - 4
Xia J.Chen Y.Liberatore KM.Selinsky BS. Tetrahedron Lett. 2003, 44: 9295 - 5
Dax K.Albert M.Hammond D.Illaszewicz C.Purkarthofer T.Tscherner M.Weber H. Monatsh. Chem. 2000, 133: 427 - 6
Pu YM.Torok DS.Ziffer H. J. Med. Chem. 1995, 38: 4120 - 7
Bartmann E.Krause J. J. Fluorine Chem. 1993, 61: 117 - 8
Thomas MG.Suckling JC.Pitt AR.Suckling KE. J. Chem. Soc., Perkin Trans. 1 1999, 3191 - 9
Sarek J.Klinot J.Dzubak P.Klinotova E.Noskova V.Krecek V.Korinkova G.Thomson JO.Janostakova A.Wang S.Parsons S.Fischer PM.Zhelev NZ.Hajduch M. J. Med. Chem. 2003, 46: 5402 - 10
Richtr V.Klinot J.Kraitr M. Chem. Listy 1998, 92: 963 - 11
Matsuzawa A.Yamamoto T. Cancer Res. 1977, 37: 4408 - 12
Li T.Wang J.Zheng X. J. Chem. Soc., Perkin Trans. 1 1998, 3957 - 13
Klinot J.Vystrcil A. Collect. Czech. Chem. Commun. 1966, 31: 1079 - 14
Sejbal J.Klinot J.Protiva J.Vystrcil A. Collect. Czech. Chem. Commun. 1986, 51: 118 - 15
Klinot J.Sejbal J.Vystrcil A. Collect. Czech. Chem. Commun. 1989, 54: 400 - 16
Nair MR.Hilgard S.Klinot J.Waisser K.Vystrcil A. Collect. Czech. Chem. Commun. 1976, 41: 770 - 17
Klinot J.Svetly J.Kudlackova D.Budesinsky M.Vystrcil A. Collect. Czech. Chem. Commun. 1979, 44: 211 - 18
Pradhan PB.Chakraborty S.Sinha PR. Ind. J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1995, 34: 540 - 19
Hajduch M, andSarek J. inventors; PCT Int. Patent Appl. WO 0190046. ; Chem. Abstr. 2002, 136, 6179 - 20
Urban M.Sarek J.Klinot J.Korinkova G.Hajduch M. J. Nat. Prod. 2004, 67: 1100 - 21
Klinot J.Vystrcil A. Collect. Czech. Chem. Commun. 1964, 29: 516 - 22
Fischer PM,Sarek J,Blaney PM,Collier P, andFergusson JR. inventors; PCT Int. Patent Appl. WO 03/045971. ; Chem. Abstr. 2003, 139, 7043