메뉴 건너뛰기




Volumn 52, Issue 18, 2009, Pages 5753-5757

Synthesis of fluorinated brassinosteroids based on alkene cross-metathesis and preliminary biological assessment

Author keywords

[No Author keywords available]

Indexed keywords

28 HOMOCASTASTERONE; 2ALPHA,3ALPHA,1',2' TETRAHYDROXY 20 (4',4',5',5',6',6',6' HEPTAFLUOROHEX 10 YL) 5ALPHA PREGNAN 6 ONE; 2ALPHA,3ALPHA,1',2' TETRAHYDROXY 7 OXA 7A HOMO 20 (4', 4',5',5',6',6',6' HEPTAFLUOROHEX 1 YL) 5ALPHA PREGNAN 6 ONE; 2ALPHA,3ALPHA,22,23 TETRAHYDROXY 7 OXA 7A HOMO 25,26,26,26,27,27,27 HEPTAFLUOROCHOLESTAN 6 ONE; 3ALPHA HYDROXY 5ALPHA PREGNAN 20 ONE; 4 AMINOBUTYRIC ACID A RECEPTOR; ALKENE DERIVATIVE; BRASSINOLIDE; BRASSINOSTEROID; CASTASTERONE; PERFLUORO COMPOUND; PERFLUOROALKYLPROPENE DERIVATIVE; PROPYLENE; UNCLASSIFIED DRUG;

EID: 70349417952     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900495f     Document Type: Article
Times cited : (37)

References (41)
  • 1
    • 33645454126 scopus 로고    scopus 로고
    • Fluorine in medicinal chemistry: A review of anti-cancer agents
    • Isanbor, C.; O'Hagan, D. Fluorine in medicinal chemistry: a review of anti-cancer agents. J. Fluorine Chem. 2006, 127, 303-319.
    • (2006) J. Fluorine Chem. , vol.127 , pp. 303-319
    • Isanbor, C.1    O'Hagan, D.2
  • 2
    • 33746356860 scopus 로고    scopus 로고
    • Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products
    • Bégué, J.-P.; Bonnet-Delpon, D. Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products. J. Fluorine Chem. 2006, 127, 992-1012.
    • J. Fluorine Chem. , vol.2006 , Issue.127 , pp. 992-1012
    • Bégué, J.-P.1    Bonnet-Delpon, D.2
  • 3
    • 33746372978 scopus 로고    scopus 로고
    • Fluorine in medicinal chemistry: Recent therapeutic applications of fluorinated small molecules
    • Kirk, K. L. Fluorine in medicinal chemistry: recent therapeutic applications of fluorinated small molecules. J. Fluorine Chem. 2006, 127, 1013-1029.
    • (2006) J. Fluorine Chem. , vol.127 , pp. 1013-1029
    • Kirk, K.L.1
  • 5
    • 70349410071 scopus 로고    scopus 로고
    • Brassinosteroids
    • Kluwer Academic Publishers: Dordrecht, The Netherlands
    • Hayat, S.; Ahmad, A. Brassinosteroids. Bioactivity and Crop Productivity; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2003.
    • (2003) Bioactivity and Crop Productivity
    • Hayat, S.1    Ahmad, A.2
  • 6
    • 33845911220 scopus 로고    scopus 로고
    • Brassinosteroid confers tolerance in Arabidopsis thaliana and Brassica napus to a range of abiotic stresses
    • DOI 10.1007/s00425-006-0361-6
    • Kagale, S.; Divi, U. K.; Krochko, J. E.; Keller, W. A.; Krishna, P. Brassinosteroid confers tolerance in Arabidopsis thaliana and Brassica napus to a range of abiotic stresses. Planta 2007, 225, 353-364. (Pubitemid 46018194)
    • (2007) Planta , vol.225 , Issue.2 , pp. 353-364
    • Kagale, S.1    Divi, U.K.2    Krochko, J.E.3    Keller, W.A.4    Krishna, P.5
  • 7
    • 33646010006 scopus 로고    scopus 로고
    • Synthesis, biological, immunological, and anticancer properties of a new brassinosteroid ligand
    • Swaczynová, J.; Šíša, M.; Hniličková, J.; Kohout, L.; Strnad, M. Synthesis, biological, immunological, and anticancer properties of a new brassinosteroid ligand. Pol. J. Chem. 2006, 80, 629-635.
    • (2006) Pol. J. Chem. , vol.80 , pp. 629-635
    • Swaczynová, J.1    Šíša, M.2    Hnilič ková, J.3    Kohout, L.4    Strnad, M.5
  • 8
    • 34249817857 scopus 로고    scopus 로고
    • Brassinolide, a plant sterol from pollen of Brassica napus L., induces apoptosis in human prostate cancer PC-3 cells
    • DOI 10.1691/ph.2007.5.6660
    • Wu, Y. D.; Lou, Y. J. Brassinolide, a plant sterol from pollen of Brassica napus L., induces apoptosis in human prostate cancer PC-3 cells. Pharmazie 2007, 62, 392-395. (Pubitemid 46847946)
    • (2007) Pharmazie , vol.62 , Issue.5 , pp. 392-395
    • Wu, Y.-D.1    Lou, Y.-J.2
  • 9
    • 9644270393 scopus 로고    scopus 로고
    • In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues
    • Michelini, F. M.; Ramirez, J. A.; Berra, A.; Galagovsky, L. R.; Alché, L. E. In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroid analogues. Steroids 2004, 69, 713-720.
    • (2004) Steroids , vol.69 , pp. 713-720
    • Michelini, F.M.1    Ramirez, J.A.2    Berra, A.3    Galagovsky, L.R.4    Alché, L.E.5
  • 10
    • 37549043140 scopus 로고    scopus 로고
    • Anticancer and antiproliferative activity of natural brassinosteroids
    • Malikova, J.; Swaczynova, J.; Kolar, Z.; Strnad, M. Anticancer and antiproliferative activity of natural brassinosteroids. Phytochemistry 2008, 69, 418-426.
    • (2008) Phytochemistry , vol.69 , pp. 418-426
    • Malikova, J.1    Swaczynova, J.2    Kolar, Z.3    Strnad, M.4
  • 11
    • 0028855127 scopus 로고
    • Metabolic conversion of 24-epibrassinolide into pentahydroxylated brassinosteroid glucosides in tomato cell cultures
    • Hai, T.; Schneider, B.; Adam, G. Metabolic conversion of 24-epibrassinolide into pentahydroxylated brassinosteroid glucosides in tomato cell cultures. Phytochemistry 1995, 40, 443-448.
    • (1995) Phytochemistry , vol.40 , pp. 443-448
    • Hai, T.1    Schneider, B.2    Adam, G.3
  • 13
    • 23844490599 scopus 로고    scopus 로고
    • Syntheses of new androstane brassinosteroids with 17beta-ester groups - Butyrates, heptafluorobutyrates, and laurates
    • DOI 10.1016/j.steroids.2005.04.005, PII S0039128X05001157
    • Šíša, M.; Hniličková, J.; Swaczynová, J.; Kohout, L. Synthesis of new androstane brassinosteroids with 17beta-ester group: butyrates, heptafluorobutyrates, and laurates. Steroids 2005, 70, 755-762. (Pubitemid 41169909)
    • (2005) Steroids , vol.70 , Issue.11 , pp. 755-762
    • Sica, M.1    Hnilickova, J.2    Swaczynova, J.3    Kohout, L.4
  • 14
    • 0345770874 scopus 로고    scopus 로고
    • Syntheses with perfluoroalkyl radicals from perfluoroalkyl iodides. a rapid survey of synthetic possibilities with emphasis on practical applications. Part one: Alkenes, alkynes and allylic compounds
    • Brace, N. O. Syntheses with perfluoroalkyl radicals from perfluoroalkyl iodides. A rapid survey of synthetic possibilities with emphasis on practical applications. Part one: alkenes, alkynes and allylic compounds. J. Fluorine Chem. 1999, 93, 1-25.
    • (1999) J. Fluorine Chem. , vol.93 , pp. 1-25
    • Brace, N.O.1
  • 15
    • 0345770871 scopus 로고    scopus 로고
    • Syntheses with perfuoroalkyl iodides. Part II. Addition to nonconjugated alkadienes; cyclization of 1,6-heptadiene, and of 4-substituted 1,6-heptadienoic compounds: Bis-allyl ether, ethyl diallylmalonate, N,N′-diallylamine and N-substituted diallylamines; and additions to homologous exo- And endo-cyclic alkenes, and to bicyclic alkenes
    • Brace, N. O. Syntheses with perfuoroalkyl iodides. Part II. Addition to nonconjugated alkadienes; cyclization of 1,6-heptadiene, and of 4-substituted 1,6-heptadienoic compounds: bis-allyl ether, ethyl diallylmalonate, N,N′-diallylamine and N-substituted diallylamines; and additions to homologous exo- and endo-cyclic alkenes, and to bicyclic alkenes. J. Fluorine Chem. 1999, 96, 101-127.
    • (1999) J. Fluorine Chem. , vol.96 , pp. 101-127
    • Brace, N.O.1
  • 16
    • 0035021925 scopus 로고    scopus 로고
    • nI homologues (n = 1-3)
    • nSH; and, useful derivatives therefrom. J. Fluorine Chem. 2001, 108, 147-175.
    • (2001) J. Fluorine Chem. , vol.108 , pp. 147-175
    • Brace, N.O.1
  • 17
    • 0038215596 scopus 로고    scopus 로고
    • Recent developments in olefin cross-metathesis
    • DOI 10.1002/anie.200200556
    • Connon, S. J.; Blechert, S. Recent developments in olefin cross-metathesis. Angew. Chem., Int. Ed. 2003, 42, 1900-1923. (Pubitemid 36565797)
    • (2003) Angewandte Chemie - International Edition , vol.42 , Issue.17 , pp. 1900-1923
    • Connon, S.J.1    Blechert, S.2
  • 18
    • 33847618281 scopus 로고    scopus 로고
    • Total syntheses of conformationally locked difluorinated pentopyranose analogues and a pentopyranosyl phosphate mimetic
    • Miles, J. A. L.; Mitchell, L.; Percy, J. M.; Singh, K.; Uneyama, E. Total syntheses of conformationally locked difluorinated pentopyranose analogues and a pentopyranosyl phosphate mimetic. J. Org. Chem. 2007, 72, 1575-1587.
    • (2007) J. Org. Chem. , vol.72 , pp. 1575-1587
    • Miles, J.A.L.1    Mitchell, L.2    Percy, J.M.3    Singh, K.4    Uneyama, E.5
  • 20
    • 2342532375 scopus 로고    scopus 로고
    • Stereoselective synthesis of internal allyl fluorides
    • Thibaudeau, S.; Fuller, R.;Gouverneur, V. Stereoselective synthesis of internal allyl fluorides. Org. Biomol. Chem. 2004, 2, 1110-1112.
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 1110-1112
    • Thibaudeau, S.1    Fuller, R.2    Gouverneur, V.3
  • 21
    • 8844242493 scopus 로고    scopus 로고
    • Synthesis of gem-difluoromethylenated massoialactone by ring-closing metathesis
    • DOI 10.1016/j.tetlet.2004.09.188, PII S0040403904023615
    • You, Z.-W.; Wu, Y.-Y.; Qing, F.-L. Synthesis of gem-difluoro-methylated massoialactone by ring-closing metathesis. Tetrahedron Lett. 2004, 45, 9479-9481. (Pubitemid 39535504)
    • (2004) Tetrahedron Letters , vol.45 , Issue.51 , pp. 9479-9481
    • You, Z.-W.1    Wu, Y.-Y.2    Qing, F.-L.3
  • 22
  • 23
    • 0742287247 scopus 로고    scopus 로고
    • Synthesis of vinyl fluorides by ring-closing metathesis
    • DOI 10.1016/j.tetlet.2003.10.127
    • Marhold, M.; Buer, A.; Hiemstra, H.; van Maarseveen, J. H.; Haufe, G. Synthesis of vinyl fluorides by ring-closing metathesis. Tetrahedron Lett. 2004, 45, 57-60. (Pubitemid 38155851)
    • (2004) Tetrahedron Letters , vol.45 , Issue.1 , pp. 57-60
    • Marhold, M.1    Buer, A.2    Hiemstra, H.3    Van Maarseveen, J.H.4    Haufe, G.5
  • 24
    • 0346392217 scopus 로고    scopus 로고
    • Fluorinated (hetero)cycles via ring-closing metathesis of fluoride- And trifluoromethyl-functionalized olefins
    • De Matteis, V.; van Delft, F. L.; de Gelder, R.; Tiebes, J.; Rutjes, F. P. J. T. Fluorinated (hetero)cycles via ring-closing metathesis of fluoride- and trifluoromethyl-functionalized olefins. Tetrahedron Lett. 2004, 45, 959-963.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 959-963
    • De Matteis, V.1    Van Delft, F.L.2    De Gelder, R.3    Tiebes, J.4    Rutjes, F.P.J.T.5
  • 25
    • 0034685462 scopus 로고    scopus 로고
    • Synthesis of functionalized olefins by cross and ring-closing metatheses
    • For an early example, see
    • For an early example, see Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. Synthesis of functionalized olefins by cross and ring-closing metatheses. J. Am. Chem. Soc. 2000, 122, 3783-3784.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 3783-3784
    • Chatterjee, A.K.1    Morgan, J.P.2    Scholl, M.3    Grubbs, R.H.4
  • 26
    • 0035823342 scopus 로고    scopus 로고
    • Ruthenium catalysed cross metathesis with fluorinated olefins
    • Imhof, S.; Randl, S.; Blechert, S. Ruthenium catalysed cross metathesis with fluorinated olefins. Chem. Commun. 2001, 1692-1693.
    • (2001) Chem. Commun. , pp. 1692-1693
    • Imhof, S.1    Randl, S.2    Blechert, S.3
  • 27
    • 33748270920 scopus 로고    scopus 로고
    • Use of the olefin metathesis reaction for highly efficient β-cyclodextrin modification
    • DOI 10.1016/j.tet.2006.03.010, PII S0040402006003905
    • Ghera, B. B.; Facheb, F.; Parrot-Lopez, H. Use of the olefin metathesis reaction for highly efficient β-cyclodextrin modification. Tetrahedron 2006, 62, 4807-4813. (Pubitemid 44316527)
    • (2006) Tetrahedron , vol.62 , Issue.20 , pp. 4807-4813
    • Ghera, B.B.1    Fache, F.2    Parrot-Lopez, H.3
  • 28
    • 53849129957 scopus 로고    scopus 로고
    • Perfluoroalkylation via cross-metathesis of alkenes with (perfluoroalkyl)propenes
    • Eignerová, B.; Dračínský, M.; Kotora, M. Perfluoroalkylation via cross-metathesis of alkenes with (perfluoroalkyl) propenes. Eur. J. Org. Chem. 2008, 4493-4499.
    • (2008) Eur. J. Org. Chem. , pp. 4493-4499
    • Eignerová, B.1    Dračínský, M.2    Kotora, M.3
  • 29
    • 23044526760 scopus 로고    scopus 로고
    • Synthesis of (20S)-2α,3α-dihydroxy-6-oxo-7-oxa-7a-homo- 5α-pregnane-20-carboxylic acid as a brassinosteroid part of ligands for binding to affinity chromatography carriers
    • For the preparation of ester 3, see
    • For the preparation of ester 3, see Kohout, L.; Chodounská, H.; Macek, M.; Strnad, M. Synthesis of (20S)-2α,3α-dihydroxy-6-oxo-7- oxa-7a-homo-5α-pregnane-20-carboxylic acid as a brassinosteroid part of ligands for binding to affinity chromatography carriers. Collect. Czech. Chem. Commun. 2000, 65, 1754-1761.
    • (2000) Collect. Czech. Chem. Commun. , vol.65 , pp. 1754-1761
    • Kohout, L.1    Chodounská, H.2    Macek, M.3    Strnad, M.4
  • 30
    • 3042741556 scopus 로고
    • A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species
    • Dess, D. B.; Martin, J. C. A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species. J. Am. Chem. Soc. 1991, 113, 7277-7287.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7277-7287
    • Dess, D.B.1    Martin, J.C.2
  • 31
    • 12344264552 scopus 로고    scopus 로고
    • Copper-catalyzed allylations of zirconocene intermediates generated from o-alkenyl or o-alkynylbenzyl ether derivatives and zirconocene-butene complex
    • Ikeuchi, Y.; Taguchi, T.; Hanzawa, Y. Copper-catalyzed allylations of zirconocene intermediates generated from o-alkenyl or o-alkynylbenzyl ether derivatives and zirconocene-butene complex. J. Org. Chem. 2005, 70, 756-759.
    • (2005) J. Org. Chem. , vol.70 , pp. 756-759
    • Ikeuchi, Y.1    Taguchi, T.2    Hanzawa, Y.3
  • 32
    • 0034734340 scopus 로고    scopus 로고
    • Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts
    • Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. L. Efficient and recyclable monomeric and dendritic Ru-based metathesis catalysts. J. Am. Chem. Soc. 2000, 122, 8168-8179.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8168-8179
    • Garber, S.B.1    Kingsbury, J.S.2    Gray, B.L.3    Hoveyda, A.L.4
  • 33
    • 0034676688 scopus 로고    scopus 로고
    • Synthesis and metathesis reactions of a phosphine-free dihydroimidazole carbene ruthenium complex
    • Gessler, S.; Randl, S.; Blechert, S. Synthesis and metathesis reactions of a phosphine-free dihydroimidazole carbene ruthenium complex. Tetrahedron Lett. 2000, 41, 9973-9976.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 9973-9976
    • Gessler, S.1    Randl, S.2    Blechert, S.3
  • 34
    • 33645362533 scopus 로고
    • Bean second internode method
    • U.S. Government Printing Office: Washington, DC
    • Mitchell, J. W.; Livingstone, G. A. Bean second internode method. In Agricultural Handbook, No. 336; U.S. Government Printing Office: Washington, DC, 1968; 26-28.
    • (1968) Agricultural Handbook, No. 336 , pp. 26-28
    • Mitchell, J.W.1    Livingstone, G.A.2
  • 35
    • 0141455630 scopus 로고
    • 13C-NMR studies of polyfluorinated hydrocarbons, carboxylic acid derivatives, alcohols and ethers
    • 13C-NMR studies of polyfluorinated hydrocarbons, carboxylic acid derivatives, alcohols and ethers. J. Fluorine Chem. 1981, 19, 163-180.
    • (1981) J. Fluorine Chem. , vol.19 , pp. 163-180
    • Von Werner, K.1    Gendorf, W.2    Wrackmeyer, B.3
  • 36
    • 0001165994 scopus 로고
    • Transition-metal complex catalyzed polyfluoroalkylation. II. Novel and convenient route to 3-poly-fluoroalkylprop-1-enes through the reaction of polyfluoroalkyl halides with allylsilanes
    • Fuchikami, T.; Ojima, I. Transition-metal complex catalyzed polyfluoroalkylation. II. Novel and convenient route to 3-poly-fluoroalkylprop- 1-enes through the reaction of polyfluoroalkyl halides with allylsilanes. Tetrahedron Lett. 1984, 25, 307-308.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 307-308
    • Fuchikami, T.1    Ojima, I.2
  • 37
    • 70349430851 scopus 로고
    • 3-(Perfluoroalkyl)-1-propenes
    • Knell, M.; Brace, N. 3-(Perfluoroalkyl)-1-propenes. DE 2 241 252, 1973.
    • (1973) DE , vol.2 , pp. 241252
    • Knell, M.1    Brace, N.2
  • 38
    • 4344641834 scopus 로고    scopus 로고
    • Reverse fluorous solid-phase extraction: Anew technique for rapid separation of fluorous compounds
    • Matsugi, M.; Curran, D. P. Reverse fluorous solid-phase extraction: Anew technique for rapid separation of fluorous compounds. Org. Lett. 2004, 6, 2717-2720.
    • (2004) Org. Lett. , vol.6 , pp. 2717-2720
    • Matsugi, M.1    Curran, D.P.2
  • 39
    • 21344486821 scopus 로고
    • New method of preparation of brassinosteroids
    • Kohout, L. New method of preparation of brassinosteroids. Collect. Czech. Chem. Commun. 1994, 59, 457-460.
    • (1994) Collect. Czech. Chem. Commun. , vol.59 , pp. 457-460
    • Kohout, L.1
  • 41
    • 0035204475 scopus 로고    scopus 로고
    • Suppressing aggressive behavior with analogs of allopregnanolone (epalon)
    • DOI 10.1016/S0039-128X(00)00215-4, PII S0039128X00002154
    • Slavíková, B.; Kasal, A.; Uhlířová, L.; Kršiak, M.; Chodounská, H.; Kohout, L. Suppressing aggressive behavior with analogs of allopregnanolone (epalon). Steroids 2001, 66, 99-105. (Pubitemid 32012555)
    • (2001) Steroids , vol.66 , Issue.2 , pp. 99-105
    • Slavikova, B.1    Kasal, A.2    Uhlirova, L.3    Krsiak, M.4    Chodounska, H.5    Kohout, L.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.