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Volumn 16, Issue 3, 2011, Pages 2443-2466

Allobetulin and its derivatives: Synthesis and biological activity

Author keywords

Allobetulin; Biological activity; Rearrangement; Triterpene

Indexed keywords

BETULIN; TRITERPENE;

EID: 79953095834     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16032443     Document Type: Article
Times cited : (85)

References (115)
  • 1
    • 73949105474 scopus 로고    scopus 로고
    • Triterpenoids
    • and the previous reviews in this series
    • Connolly, J.D.; Hill, R.A. Triterpenoids. Nat. Prod. Rep. 2010, 27, 79-132 and the previous reviews in this series.
    • (2010) Nat. Prod. Rep. , vol.27 , pp. 79-132
    • Connolly, J.D.1    Hill, R.A.2
  • 4
    • 3242811172 scopus 로고    scopus 로고
    • Coumaroyl triterpene lactone, phenolic and naphthalene glycoside from stem bark of Diospyros angustifolia
    • DOI 10.1016/j.phytochem.2004.03.010, PII S0031942204001104
    • Pathak, A.; Kulshreshtha, D.K.; Maurya, R. Coumaryl triterpene lactone, phenolic and naphthalene glycoside from stem bark of Diospyros angustifolia. Phytochemistry 2004, 65, 2153-2158. (Pubitemid 38981671)
    • (2004) Phytochemistry , vol.65 , Issue.14 , pp. 2153-2158
    • Pathak, A.1    Kulshreshtha, D.K.2    Maurya, R.3
  • 5
    • 0000089032 scopus 로고
    • Zur kenntnis des betulins
    • Schulze, H.; Pieroh, K. Zur Kenntnis des Betulins. Chem. Ber. 1922, 55, 2322-2346.
    • (1922) Chem. Ber. , vol.55 , pp. 2322-2346
    • Schulze, H.1    Pieroh, K.2
  • 6
    • 51649134243 scopus 로고
    • Untersuchungen auf dem Gebiete der Phytochemie-Über das Allobetulin
    • Dischendorfer, O.; Juvan, H. Untersuchungen auf dem Gebiete der Phytochemie-Über das Allobetulin. Monatsh. Chem. 1930, 52, 272-281.
    • (1930) Monatsh. Chem. , vol.52 , pp. 272-281
    • Dischendorfer, O.1    Juvan, H.2
  • 7
    • 37049154414 scopus 로고
    • The chemistry of the triterpenes. Part X. The structures of some isomerisation products from betulin and betulinic acid
    • Davy, G.S.; Halsall, T.G.; Jones, E.R.H.; Meakins, G.D. The chemistry of the triterpenes. Part X. The structures of some isomerisation products from betulin and betulinic acid. J. Chem. Soc. 1951, 2702-2705.
    • (1951) J. Chem. Soc. , pp. 2702-2705
    • Davy, G.S.1    Halsall, T.G.2    Jones, E.R.H.3    Meakins, G.D.4
  • 10
    • 0002939877 scopus 로고
    • Some relative configurations in rings C, D, and E of the β -amyrin and the lupeol group of triterpenoids
    • Barton, D.H.R.; Holness, N.J.; Triterpenoids. V. Some relative configurations in rings C, D, and E of the β -amyrin and the lupeol group of triterpenoids. J. Chem. Soc. 1952, 78-92.
    • (1952) J. Chem. Soc. , pp. 78-92
    • Barton, D.H.R.1    Holness, N.J.2    Triterpenoids., V.3
  • 11
    • 0007356637 scopus 로고
    • Triterpenoids in the bark of mountain ash Sorbus aucuparia
    • Lawrie, W.; McLean, J.; Taylor, G.R. Triterpenoids in the bark of mountain ash Sorbus aucuparia. J. Chem. Soc. 1960, 4303-4308.
    • (1960) J. Chem. Soc. , pp. 4303-4308
    • Lawrie, W.1    McLean, J.2    Taylor, G.R.3
  • 12
    • 0017084874 scopus 로고
    • The chemistry of the Euphorbiaceae. XXIV. Lup-20(29)-ene-3β,16β ,28-triol from Beyeria brevifolia var brevifolia
    • Errington, S.G.; Ghisalberti, E.L.; Jefferies, P.R. The chemistry of the Euphorbiaceae. XXIV. Lup-20(29)-ene-3β,16β ,28-triol from Beyeria brevifolia var brevifolia. Aust. J. Chem. 1976, 29, 1809-1814.
    • (1976) Aust. J. Chem. , vol.29 , pp. 1809-1814
    • Errington, S.G.1    Ghisalberti, E.L.2    Jefferies, P.R.3
  • 13
    • 21344491725 scopus 로고
    • Triterpenoids. Part XI. Isomerization of betulin and its derivatives
    • Linkowska, E. Triterpenoids. Part XI. Isomerization of betulin and its derivatives. Pol. J. Chem. 1994, 68, 875-876.
    • (1994) Pol. J. Chem. , vol.68 , pp. 875-876
    • Linkowska, E.1
  • 14
    • 33748737575 scopus 로고    scopus 로고
    • Simple synthesis of allobetulin, 28-oxyallobetulin and related biomarkers from betulin and betulinic acid catalysed by solid acids
    • Li, T.S.; Wang, J.X.; Zheng, X.J. Simple synthesis of allobetulin, 28-oxyallobetulin and related biomarkers from betulin and betulinic acid catalysed by solid acids. J. Chem. Soc. Perkin Trans. 1 1998, 3957-3965.
    • (1998) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 3957-3965
    • Li, T.S.1    Wang, J.X.2    Zheng, X.J.3
  • 15
    • 0034940099 scopus 로고    scopus 로고
    • Synthesis of betulin derivatives with solid supported reagents
    • DOI 10.1081/SCC-100104070
    • Lavoie S.; Pichette A.; Garneau F.-X.; Girard, M.; Gaudet, D. Synthesis of betulin derivatives with solid supported reagents. Synth. Commun. 2001, 31, 1565-1571. (Pubitemid 32642297)
    • (2001) Synthetic Communications , vol.31 , Issue.10 , pp. 1565-1571
    • Lavoie, S.1    Pichette, A.2    Garneau, F.-X.3    Girard, M.4    Gaudet, D.5
  • 18
    • 58849131044 scopus 로고    scopus 로고
    • Bismuth triflate-catalyzed Wagner-Meerwein rearrangement in terpenes. Application to the synthesis of the 18a-oleanone core and A-neo-18a-oleanene compounds from lupanes
    • Salvador, J.A.R.; Pinto, R.M.A.; Santos, R.C.; Le Roux, C.; Beja, A.M.; Paix?o, J.A. Bismuth triflate-catalyzed Wagner-Meerwein rearrangement in terpenes. Application to the synthesis of the 18a-oleanone core and A-neo-18a-oleanene compounds from lupanes. Org. Biomol. Chem. 2009, 7, 508-517.
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 508-517
    • Salvador, J.A.R.1    Pinto, R.M.A.2    Santos, R.C.3    Le Roux, C.4    Beja, A.M.5    Paixao, J.A.6
  • 19
    • 79953089883 scopus 로고    scopus 로고
    • Method of producing allobetulin from birch bark via isomerization of betulinol
    • CA 2009
    • Levdanskii, V.A.; Levdanskii, A.V.; Kuznetsov, B.N. Method of producing allobetulin from birch bark via isomerization of betulinol. Russ. Patent RU 2374261, 2009, [CA 2009, 151, 571219].
    • (2009) Russ. Patent RU 2374261 , vol.151 , pp. 571219
    • Levdanskii, V.A.1    Levdanskii, A.V.2    Kuznetsov, B.N.3
  • 21
    • 36849035421 scopus 로고    scopus 로고
    • Isolation of betulin and rearrangement to allobetulin. A biomimetic natural product synthesis
    • Green, B.; Bentley, M.D.; Chung, B.Y.; Lynch, N.G.; Jensen, B.L. Isolation of betulin and rearrangement to allobetulin. A biomimetic natural product synthesis. J. Chem. Ed. 2007, 84, 1985-1987. (Pubitemid 350225778)
    • (2007) Journal of Chemical Education , vol.84 , Issue.12 , pp. 1985-1987
    • Green, B.1    Bentley, M.D.2    Chung, B.Y.3    Lynch, N.G.4    Jensen, B.L.5
  • 22
    • 34447625709 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationship study of cytotoxic germanicane- and lupane-type 3β-O-monodesmosidic saponins starting from betulin
    • DOI 10.1016/j.bmc.2007.06.033, PII S096808960700569X
    • Thibeault, D.; Gauthier, C.; Legault, J.; Bouchard, J.; Dufour, P.; Pichette, A. Synthesis and structure-activity relationship study of cytotoxic germanicane- and lupane-type 3Β-Omonodesmosidic saponins starting from betulin. Bioorg. Med. Chem. 2007, 15, 6144-6157. (Pubitemid 47090244)
    • (2007) Bioorganic and Medicinal Chemistry , vol.15 , Issue.18 , pp. 6144-6157
    • Thibeault, D.1    Gauthier, C.2    Legault, J.3    Bouchard, J.4    Dufour, P.5    Pichette, A.6
  • 27
    • 35549010096 scopus 로고
    • Novel method for reductive cleavage of triterpenoid lactones with lithium in ethylenediamine
    • Pradhan, B.P.; Chakraborty, D.K.; Roy, A. Novel method for reductive cleavage of triterpenoid lactones with lithium in ethylenediamine. Ind. J. Chem. B Org. Chem. Med. Chem. 1993, 32B, 721-725.
    • (1993) Ind. J. Chem. B Org. Chem. Med. Chem. , vol.32 B , pp. 721-725
    • Pradhan, B.P.1    Chakraborty, D.K.2    Roy, A.3
  • 28
    • 0025959951 scopus 로고
    • Studies on the reactions of Nbromosuccinimide in dimethyl sulfoxide: Part IV. Action on lupenyl acetate
    • Pradhan, B.P.; Chakraborty, D.K.; Dutta, S.; Ghosh, R.; Roy, A. Studies on the reactions of Nbromosuccinimide in dimethyl sulfoxide: Part IV. Action on lupenyl acetate. Ind. J. Chem. B Org. Chem. Med. Chem. 1991, 30B, 32-37.
    • (1991) Ind. J. Chem. B Org. Chem. Med. Chem. , vol.30 B , pp. 32-37
    • Pradhan, B.P.1    Chakraborty, D.K.2    Dutta, S.3    Ghosh, R.4    Roy, A.5
  • 30
    • 37049154415 scopus 로고
    • The chemistry of the triterpenes. Part IX. Elucidation of the Betulin-Oleanolic acid relationship
    • Davy, G.S.; Halsall, T.G.; Jones, E.R.H. The chemistry of the triterpenes. Part IX. Elucidation of the Betulin-Oleanolic acid relationship. J. Chem. Soc. 1951, 2696-2702.
    • (1951) J. Chem. Soc. , pp. 2696-2702
    • Davy, G.S.1    Halsall, T.G.2    Jones, E.R.H.3
  • 31
    • 75449104167 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of antitumouractive betulin derivatives
    • Csuk, R.; Barthel, A.; Kluge, R.; Kommera, H. Synthesis and biological evaluation of antitumouractive betulin derivatives. Bioorg. Med. Chem. 2010, 18, 1344-1355.
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 1344-1355
    • Csuk, R.1    Barthel, A.2    Kluge, R.3    Kommera, H.4
  • 33
    • 58049165862 scopus 로고    scopus 로고
    • Synthesis of lupane and 19β,28-epoxy-18a-oleane 2,3-seco-derivatives based on betulin
    • Tolmacheva, I.A.; Nazarov, A.V.; Maiorova, O.A.; Grishko, V.V. Synthesis of lupane and 19β,28-epoxy-18a-oleane 2,3-seco-derivatives based on betulin. Chem. Nat. Comp. 2008, 44, 606-611.
    • (2008) Chem. Nat. Comp. , vol.44 , pp. 606-611
    • Tolmacheva, I.A.1    Nazarov, A.V.2    Maiorova, O.A.3    Grishko, V.V.4
  • 34
    • 79953094538 scopus 로고    scopus 로고
    • Anti-fungal formulation of triterpene and essential oil
    • CA 2004
    • Carlson, R.M.; Gibson, D.J. Anti-fungal formulation of triterpene and essential oil. PCT Int. Appl. WO 2004089357, 2004, [CA 2004, 141, 370537].
    • (2004) PCT Int. Appl. WO 2004089357 , vol.141 , pp. 370537
    • Carlson, R.M.1    Gibson, D.J.2
  • 35
    • 79953125203 scopus 로고    scopus 로고
    • Preparation of allobetulin triterpenoids for therapeutic use in the treatment of herpes virus infection
    • CA 2002
    • Carlson, R.M. Preparation of allobetulin triterpenoids for therapeutic use in the treatment of herpes virus infection. U.S. Patent US 6369101, 2002, [CA 2002, 136, 279583].
    • (2002) U.S. Patent US 6369101 , vol.136 , pp. 279583
    • Carlson, R.M.1
  • 38
    • 33748924457 scopus 로고    scopus 로고
    • Synthesis of spiro[(6-phenyl-3,4-dihydro-2H-1,3-dioxine)-2R(S), 3'-(19',28'-oxidooleanan)]-4-ones and X-ray diffraction analysis of their configuration
    • DOI 10.1007/s10947-006-0256-1
    • Rybalova, T.V.; Galitov, Y.V.; Nekrasov, D.D.; Rubtsov, A.E.; Tolstikov, A.G. Synthesis of spiro[(6-phenyl-3,4-dihydro-2H-1,3-dioxine)-2R(S), 3'-(19',28'-oxidooleanan)]-4-ones and X-ray diffraction analysis of their configuration. J. Struct. Chem. 2005, 46, 1126-1130. (Pubitemid 44431558)
    • (2005) Journal of Structural Chemistry , vol.46 , Issue.6 , pp. 1126-1130
    • Rybalova, T.V.1    Gatilov, Yu.V.2    Nekrasov, D.D.3    Rubtsov, A.E.4    Tolstikov, A.G.5
  • 39
    • 79953074675 scopus 로고    scopus 로고
    • Effect of substituents in the cumulene and aryl fragments of aroylketenes on the stereoselectivity of Diels-Alder heteroreaction with mono-, bi, and polycyclic terpenoids containing a carbonyl group
    • Nekrasov, D.D.; Obukhova, A.S.; Lisovenko, N.Y.; Roubtsov, A.E. Effect of substituents in the cumulene and aryl fragments of aroylketenes on the stereoselectivity of Diels-Alder heteroreaction with mono-, bi, and polycyclic terpenoids containing a carbonyl group. Chem. Het. Comp. 2010, 46, 413-418.
    • (2010) Chem. Het. Comp. , vol.46 , pp. 413-418
    • Nekrasov, D.D.1    Obukhova, A.S.2    Lisovenko, N.Y.3    Roubtsov, A.E.4
  • 41
    • 65249134000 scopus 로고    scopus 로고
    • Efficient synthesis of morolic acid and relared triterpenes starting from betulin
    • Zhang, P.; Hao, J.; Liu, J.; Zhang, L.; Sun, H. Efficient synthesis of morolic acid and relared triterpenes starting from betulin. Tetrahedron 2009, 65, 4304-4309.
    • (2009) Tetrahedron , vol.65 , pp. 4304-4309
    • Zhang, P.1    Hao, J.2    Liu, J.3    Zhang, L.4    Sun, H.5
  • 42
    • 79953103242 scopus 로고
    • Preparation and Forster reaction of 19β, 28-epoxy-3-oxo-2- antioximino- la -cyano-18a H-oleanane and the bromination of 19β,28-epoxy-3-oxo-1a-cyano-18aHoleanane
    • Huneck, S. Triterpenes. XV. Preparation and Forster reaction of 19β, 28-epoxy-3-oxo-2-antioximino- la -cyano-18a H-oleanane and the bromination of 19β,28-epoxy-3-oxo-1a-cyano-18aHoleanane. Chem. Ber. 1965, 98, 3204-3209.
    • (1965) Chem. Ber. , vol.98 , pp. 3204-3209
    • Huneck, S.1    Triterpenes, X.V.2
  • 43
    • 0035536487 scopus 로고    scopus 로고
    • Synthesis of quinoxalines fused with triterpenes, ursolic acid and betulin derivatives
    • Korovin, A.V.; Tkachev, A.V. Synthesis of quinoxalines fused with triterpenes, ursolic acid and betulin derivatives. Russ. Chem. Bull. 2001, 50, 304-310.
    • (2001) Russ. Chem. Bull. , vol.50 , pp. 304-310
    • Korovin, A.V.1    Tkachev, A.V.2
  • 44
    • 79953095134 scopus 로고
    • Triterpenes. Part LXXXI. Ethylene dithioketals in ring A of 19β, 28-epoxy-18a -oleanane; mass spectra and reduction with deuterated Raney nickel
    • Protiva, J.; Ocadlik, R.; Klinotova, E.; Klinot, J.; Vystrcil, A. Triterpenes. Part LXXXI. Ethylene dithioketals in ring A of 19β, 28-epoxy-18a -oleanane; mass spectra and reduction with deuterated Raney nickel. Coll. Czech Chem. Commun. 1987, 52, 501-507.
    • (1987) Coll. Czech Chem. Commun. , vol.52 , pp. 501-507
    • Protiva, J.1    Ocadlik, R.2    Klinotova, E.3    Klinot, J.4    Vystrcil, A.5
  • 45
    • 0141825626 scopus 로고
    • Photochemical transformations. 2. Preparation of 19β, 28-epoxy-3- oxo-2-diazo-18a H-oleanane and its photochemical conversion to A-nor compounds
    • Huneck, S. Triterpenes. X. Photochemical transformations. 2. Preparation of 19β, 28-epoxy-3- oxo-2-diazo-18a H-oleanane and its photochemical conversion to A-nor compounds. Chem. Ber. 1965, 98, 1837-1857.
    • (1965) Chem. Ber. , vol.98 , pp. 1837-1857
    • Huneck, S.1    Triterpenes, X.2
  • 46
    • 84982334367 scopus 로고
    • Polyterpenes and polyterpenoids. LXVIII. Betulin
    • Ruzicka, L.; Brungger, H.; Gustus, E.L. Polyterpenes and polyterpenoids. LXVIII. Betulin. Helv. Chim. Acta 1932, 15, 634-648.
    • (1932) Helv. Chim. Acta , vol.15 , pp. 634-648
    • Ruzicka, L.1    Brungger, H.2    Gustus, E.L.3
  • 47
    • 18744383741 scopus 로고
    • Side-products in the conversion of allobetulin to heterobetulin
    • Klinot, J.; Vystrcil, A. Side-products in the conversion of allobetulin to heterobetulin. Collect. Czech. Chem. Commun. 1964, 29, 516-530.
    • (1964) Collect. Czech. Chem. Commun. , vol.29 , pp. 516-530
    • Klinot, J.1    Vystrcil, A.2
  • 49
    • 0022630107 scopus 로고
    • Reactions of triterpenoid ketones with sulfur and morpholine under the conditions of Willgerodt-Kindler reaction
    • Sejbal, J.; Klinot, J.; Protiva, J.; Vystrcil, A. Triterpenes. Part. LXXIII. Reactions of triterpenoid ketones with sulfur and morpholine under Willgerodt-Kindler reaction conditions. Collect. Czech. Chem. Commun. 1986, 51, 118-127. (Pubitemid 16209524)
    • (1986) Collection of Czechoslovak Chemical Communications , vol.51 , Issue.1 , pp. 118-127
    • Sejbal, J.1    Klinot, J.2    Protiva, J.3    Vystrcil, A.4
  • 50
    • 37049050990 scopus 로고
    • Long-range effects in alicyclic systems. II. Rates of condensation of some triterpenoid ketones with benzaldehyde
    • Barton, D.H.R.; Head, A.J.; May, P.J. Long-range effects in alicyclic systems. II. Rates of condensation of some triterpenoid ketones with benzaldehyde. J. Chem. Soc. 1957, 935-944.
    • (1957) J. Chem. Soc. , pp. 935-944
    • Barton, D.H.R.1    Head, A.J.2    May, P.J.3
  • 51
    • 2142679213 scopus 로고
    • Condensation of 3-oxotriterpenes with esters and synthesis of C-substituted triterpenoid azoles
    • Triterpenoids. XXI.
    • Kim, H.O.; Tolstikov, G.A.; Bazalitskaya, V.S. Triterpenoids. XXI. Condensation of 3- oxotriterpenes with esters and synthesis of C-substituted triterpenoid azoles. Zh. Obsh. Khim. 1970, 40, 492-497.
    • (1970) Zh. Obsh. Khim. , vol.40 , pp. 492-497
    • Kim, H.O.1    Tolstikov, G.A.2    Bazalitskaya, V.S.3
  • 52
    • 18744390880 scopus 로고
    • Triterpenes.59 Preparation of 2-methyl-3-oxotriterpenoids of 18-a-oleanane series and the conformation of ring A
    • Klinot, J.; Svetly, J.; Kudlácková, D.; Budešínsky, M.; Vystrcil, A. Triterpenes.59 Preparation of 2-methyl-3-oxotriterpenoids of 18-a-oleanane series and the conformation of ring A. Collect. Czech. Chem. Commun. 1979, 44, 211-225.
    • (1979) Collect. Czech. Chem. Commun. , vol.44 , pp. 211-225
    • Klinot, J.1    Svetly, J.2    Kudlácková, D.3    Budešínsky, M.4    Vystrcil, A.5
  • 54
    • 18744395271 scopus 로고    scopus 로고
    • Fluorination of betulinines and other triterpenoids with DAST
    • DOI 10.1055/s-2005-861861, T10304SS
    • Biedermann, D.; Sarek, J.; Klinot, J.; Hajduch, M.; Dzubak, P. Fluorination of betulinines and other triterpenoids with DAST. Synthesis 2005, 1157-1163. (Pubitemid 40676008)
    • (2005) Synthesis , Issue.7 , pp. 1157-1163
    • Biedermann, D.1    Sarek, J.2    Klinot, J.3    Hajduch, M.4    Dzubak, P.5
  • 55
    • 79953099236 scopus 로고
    • Conformation of epimeric 2-bromoallobetulones
    • Klinot, J.; Vystrcil, A. Conformation of epimeric 2-bromoallobetulones. Chem. Ind. 1960, 1360-1361.
    • (1960) Chem. Ind. , pp. 1360-1361
    • Klinot, J.1    Vystrcil, A.2
  • 56
    • 0002316527 scopus 로고
    • Studies of cyclic ketones. VIII. Preparation and properties of polycyclic a-diketones
    • Hanna, R.; Ourisson, G. Studies of cyclic ketones. VIII. Preparation and properties of polycyclic a-diketones. Bull. Soc. Chim. Fr. 1961, 1945-1951.
    • (1961) Bull. Soc. Chim. Fr. , pp. 1945-1951
    • Hanna, R.1    Ourisson, G.2
  • 57
    • 37049057623 scopus 로고
    • Compounds related to the steroid hormones. II. Action of hydrogen bromide on 2-bromo-3-oxo-?1-5a -steroids
    • Green, G.F.H.; Long, A.G. Compounds related to the steroid hormones. II. Action of hydrogen bromide on 2-bromo-3-oxo-?1-5a -steroids. J. Chem. Soc. 1961, 2532-2543.
    • (1961) J. Chem. Soc. , pp. 2532-2543
    • Green, G.F.H.1    Long, A.G.2
  • 58
    • 4243359942 scopus 로고
    • Cyclic ketones. XIV. Conformation of 2-bromo- and 2,2-dibromo-3- oxotriterpenes
    • Lehn, J.M.; Ourisson, G. Cyclic ketones. XIV. Conformation of 2-bromo- and 2,2-dibromo-3- oxotriterpenes. Bull. Soc. Chim. Fr. 1963, 1113-21.
    • (1963) Bull. Soc. Chim. Fr. , pp. 1113-21
    • Lehn, J.M.1    Ourisson, G.2
  • 59
    • 0002285784 scopus 로고
    • Triterpenes. 7. Stereochemistry of 2-bromo derivatives of allobetulin and alloheterobetulin
    • Klinot, J.; Vystrcil, A. Triterpenes. 7. Stereochemistry of 2-bromo derivatives of allobetulin and alloheterobetulin Collect. Czech. Chem. Commun. 1966, 31, 1079-1091.
    • (1966) Collect. Czech. Chem. Commun. , vol.31 , pp. 1079-1091
    • Klinot, J.1    Vystrcil, A.2
  • 60
    • 79953090210 scopus 로고    scopus 로고
    • Preparation of betulin type triterpenoid derivatives as antitumor agents
    • CA 2001
    • Hajduch, M.; Sarek, J. Preparation of betulin type triterpenoid derivatives as antitumor agents. PCT Int. Appl. WO 2001090096, 2001, [CA 2001, 136, 6180].
    • (2001) PCT Int. Appl. WO 2001090096 , vol.136 , pp. 6180
    • Hajduch, M.1    Sarek, J.2
  • 61
    • 33744545899 scopus 로고
    • Triterpenes. XLIII. Conformation of ring A of 2,3-disubstituted triterpenes with chlorine or an alkoxy group in position 2
    • Klinot, J.; Richtr, V.; Vystrcil, A. Triterpenes. XLIII. Conformation of ring A of 2,3-disubstituted triterpenes with chlorine or an alkoxy group in position 2. Collect. Czech. Chem. Commun. 1975, 40, 1758-1767.
    • (1975) Collect. Czech. Chem. Commun. , vol.40 , pp. 1758-1767
    • Klinot, J.1    Richtr, V.2    Vystrcil, A.3
  • 62
    • 33748190339 scopus 로고
    • Triterpenes. CII. Crystal structure and conformation of ring A of 2a-bromo-19β,28-epoxy-18a-oleanan-3-one
    • Novotny, J.; Podlaha, J.; Klinot, J. Triterpenes. CII. Crystal structure and conformation of ring A of 2a-bromo-19β,28-epoxy-18a-oleanan-3-one. Collect. Czech. Chem. Commun. 1993, 58, 2737-2744.
    • (1993) Collect. Czech. Chem. Commun. , vol.58 , pp. 2737-2744
    • Novotny, J.1    Podlaha, J.2    Klinot, J.3
  • 63
    • 3242668439 scopus 로고
    • Triterpenoids. XXIII. Synthesis and reactions of acetylenic derivatives of triterpenes
    • Tolstikova, L.F.; Tolstikov, G.A. Triterpenoids. XXIII. Synthesis and reactions of acetylenic derivatives of triterpenes. Izv. Akad. Nauk Kazakh. SSR, Ser. Khim. 1971, 21, 65-71.
    • (1971) Izv. Akad. Nauk Kazakh. SSR, Ser. Khim. , vol.21 , pp. 65-71
    • Tolstikova, L.F.1    Tolstikov, G.A.2
  • 64
    • 40649103827 scopus 로고    scopus 로고
    • Reaction of lupane and oleane triterpenoids with Lawesson's reagent
    • Kvasnica, M.; Rudovska, I.; Cisarova, I.; Sarek, J. Reaction of lupane and oleane triterpenoids with Lawesson's reagent. Tetrahedron 2008, 64, 3736-3743.
    • (2008) Tetrahedron , vol.64 , pp. 3736-3743
    • Kvasnica, M.1    Rudovska, I.2    Cisarova, I.3    Sarek, J.4
  • 65
    • 0002126175 scopus 로고
    • Triterpenes. Part LXXXIII. Reaction of 3-keto and 2- ketotriterpenoids with 3-chloroperoxybenzoic acid in aliphatic alcohols. A new method of preparation of a-hydroxy ketones
    • Sejbal, J.; Klinot, J.; Vystrcil, A. Triterpenes. Part LXXXIII. Reaction of 3-keto and 2- ketotriterpenoids with 3-chloroperoxybenzoic acid in aliphatic alcohols. A new method of preparation of a-hydroxy ketones. Collect. Czech. Chem. Commun. 1987, 52, 1052-1061.
    • (1987) Collect. Czech. Chem. Commun. , vol.52 , pp. 1052-1061
    • Sejbal, J.1    Klinot, J.2    Vystrcil, A.3
  • 67
    • 0042418063 scopus 로고
    • Triterpenes. LXXXV. Photolysis of 19β, 28-epoxy-18a - oleanan-2β -ol nitrites: Functionalization of 10β - and 8β -methyl groups
    • Sejbal, J.; Klinot, J.; Vystrcil, A. Triterpenes. LXXXV. Photolysis of 19β, 28-epoxy-18a - oleanan-2β -ol nitrites: functionalization of 10β - and 8β -methyl groups. Collect. Czech. Chem. Commun. 1988, 53, 118-131.
    • (1988) Collect. Czech. Chem. Commun. , vol.53 , pp. 118-131
    • Sejbal, J.1    Klinot, J.2    Vystrcil, A.3
  • 68
    • 30244436660 scopus 로고
    • Triterpenes. XCIV. Photolyses and pyrolyses of triterpenoid nitrites
    • Sejbal, J.; Klinot, J.; Budesinsky, M. Triterpenes. XCIV. Photolyses and pyrolyses of triterpenoid nitrites. Collect. Czech. Chem. Commun. 1991, 56, 1732-1743.
    • (1991) Collect. Czech. Chem. Commun. , vol.56 , pp. 1732-1743
    • Sejbal, J.1    Klinot, J.2    Budesinsky, M.3
  • 69
    • 30244494687 scopus 로고    scopus 로고
    • Triterpenes. Part CV. Oleanane triterpenoids functionalized at C-25 and C-26
    • Sejbal, J.; Klinot, J.; Budesinsky, M. Triterpenes. Part CV. Oleanane triterpenoids functionalized at C-25 and C-26. Collect. Czech. Chem. Commun. 1996, 61, 1360-1370.
    • (1996) Collect. Czech. Chem. Commun. , vol.61 , pp. 1360-1370
    • Sejbal, J.1    Klinot, J.2    Budesinsky, M.3
  • 71
    • 79953088363 scopus 로고    scopus 로고
    • Preparation of triterpene derivatives having fungicidal activity against yeast
    • CA 2002
    • Krasutsky, P.A.; Carlson, R.M. Preparation of triterpene derivatives having fungicidal activity against yeast. PCT Int. Appl. WO 2002026761, 2002, [CA 2002, 136, 294955].
    • (2002) PCT Int. Appl. WO. 2002026761 , vol.136 , pp. 294955
    • Krasutsky, P.A.1    Carlson, R.M.2
  • 72
    • 79953069337 scopus 로고    scopus 로고
    • Preparation of triterpene quaternary salts having antibacterial, antifungal, and surfactant properties
    • CA 2003
    • Krasutsky, P.A.; Avilov, D.V. Preparation of triterpene quaternary salts having antibacterial, antifungal, and surfactant properties. PCT Int. Appl. WO 2003062260, 2003, [CA 2003, 139, 133696].
    • (2003) PCT Int. Appl. WO. 2003062260 , vol.139 , pp. 133696
    • Krasutsky, P.A.1    Avilov, D.V.2
  • 73
    • 32044463812 scopus 로고    scopus 로고
    • Benzoylacetylation of allobetulin and allobetulone oxime by benzoylketene generated in situ during thermolysis of 5-phenyl-2,3-dihydrofuran-2,3-dione
    • Nekrasov, D.D.; Obukhova, A.S. Benzoylacetylation of allobetulin and allobetulone oxime by benzoylketene generated in situ during thermolysis of 5-phenyl-2,3-dihydrofuran-2,3-dione. Chem. Het. Comp. 2005, 41, 1426-1427.
    • (2005) Chem. Het. Comp. , vol.41 , pp. 1426-1427
    • Nekrasov, D.D.1    Obukhova, A.S.2
  • 76
    • 0039932462 scopus 로고    scopus 로고
    • Stereoselective synthesis of triterpene 3-O-2-deoxy-A-glycosides
    • Baltina, L.A.; Flekhter, O.B.; Vasiljieva, E.V. Stereoselective synthesis of triterpene 3-O-2- deoxy-a -glycosides. Mendeleev Commun. 1996, 63-64.
    • (1996) Mendeleev Commun. , pp. 63-64
    • Baltina, L.A.1    Flekhter, O.B.2    Vasiljieva, E.V.3
  • 78
    • 33847297590 scopus 로고    scopus 로고
    • Synthesis of methyl esters of betulinic acid 2-deoxy-a-glycosides and 28-oxo-19,28-epoxyoleanane
    • Flekhter, O.B.; Medvedeva, N.I.; Tret'yakova, E.V.; Galin, F.Z.; Tolstikov, G.A. Synthesis of methyl esters of betulinic acid 2-deoxy-a-glycosides and 28-oxo-19,28-epoxyoleanane. Chem. Nat. Comp. 2006, 42, 706-709.
    • (2006) Chem. Nat. Comp. , vol.42 , pp. 706-709
    • Flekhter, O.B.1    Medvedeva, N.I.2    Tret'yakova, E.V.3    Galin, F.Z.4    Tolstikov, G.A.5
  • 80
    • 63549116461 scopus 로고    scopus 로고
    • Synthesis cytotoxicity and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products
    • Gauthier, C.; Legault, J.; Piochon, M.; Lavoie, S.; Tremblay, S.; Pichette, A. Synthesis, cytotoxicity and haemolytic activity of chacotrioside lupane-type neosaponins and their germanicane-type rearrangement products. Bioorg. Med. Chem. Lett. 2009, 19, 2310-2314.
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 2310-2314
    • Gauthier, C.1    Legault, J.2    Piochon, M.3    Lavoie, S.4    Tremblay, S.5    Pichette, A.6
  • 81
    • 79953068146 scopus 로고    scopus 로고
    • Synthesis of triterpene derivatives as antitumor or antiinflammatory agents
    • CA 2008
    • Pichette, A.; Legault, J.; Gauthier, C. Synthesis of triterpene derivatives as antitumor or antiinflammatory agents. Can. Pat. Appl. CA 2586614, 2008, [CA 2008, 148, 538411].
    • (2008) Can. Pat. Appl. CA 2586614 , vol.148 , pp. 538411
    • Pichette, A.1    Legault, J.2    Gauthier, C.3
  • 82
    • 33744508977 scopus 로고
    • Triterpenes. XX. Participation of dimethylformamide in the addition of halogens to the 2-double bond - A route for the preparation of Β-epoxides
    • Klinot, J.; Waisser, K.; Streinz, L.; Vystrcil, A. Triterpenes. XX. Participation of dimethylformamide in the addition of halogens to the 2-double bond-a route for the preparation of Β-epoxides. Collect. Czech. Chem. Commun. 1970, 35, 3610-3617.
    • (1970) Collect. Czech. Chem. Commun. , vol.35 , pp. 3610-3617
    • Klinot, J.1    Waisser, K.2    Streinz, L.3    Vystrcil, A.4
  • 83
    • 79953123272 scopus 로고
    • Triterpenes. IX. Reaction of isomeric 2,3-epoxides with a Grignard reagent
    • Klinot, J.; Krumpolc, M.; Vystrcil, A. Triterpenes. IX. Reaction of isomeric 2,3-epoxides with a Grignard reagent. Collect. Czech. Chem. Commun. 1966, 31, 3174-3181.
    • (1966) Collect. Czech. Chem. Commun. , vol.31 , pp. 3174-3181
    • Klinot, J.1    Krumpolc, M.2    Vystrcil, A.3
  • 89
    • 4444330903 scopus 로고
    • Steroids and related natural products. VI. The structure of a-apoallobetulin
    • Pettit, G.R.; Green, B.W.; Bowyer, W.J. Steroids and related natural products. VI. The structure of a-apoallobetulin. J. Org. Chem. 1961, 26, 2879-2883.
    • (1961) J. Org. Chem. , vol.26 , pp. 2879-2883
    • Pettit, G.R.1    Green, B.W.2    Bowyer, W.J.3
  • 91
    • 79953112248 scopus 로고    scopus 로고
    • Substituted taraxastanes useful for treating viral infections
    • CA 2007
    • Bradbury, B.J.; Huang, M. Substituted taraxastanes useful for treating viral infections. U.S. Pat. Appl. US 20070197646, 2007, [CA 2007, 147, 269186].
    • (2007) U.S. Pat. Appl. US 20070197646 , vol.147 , pp. 269186
    • Bradbury, B.J.1    Huang, M.2
  • 94
    • 37049119699 scopus 로고
    • Exhaustive Baeyer-Villiger oxidation of the allobetulone triterpenoid
    • Hase, T. Exhaustive Baeyer-Villiger oxidation of the allobetulone triterpenoid. J. Chem. Soc. Chem. Commun. 1972, 755-756.
    • (1972) J. Chem. Soc. Chem. Commun. , pp. 755-756
    • Hase, T.1
  • 95
    • 0002132870 scopus 로고
    • Triterpenes. Part LXXI. Oxidation of 19β, 28-epoxy-18a-oleanan-3-one and -1-one with peracids
    • Sejbal, J.; Klinot, J.; Hrncirova, D.; Vystrcil, A. Triterpenes. Part LXXI. Oxidation of 19β, 28- epoxy-18a -oleanan-3-one and -1-one with peracids. Collect. Czech. Chem. Commun. 1985, 50, 2753-2759.
    • (1985) Collect. Czech. Chem. Commun. , vol.50 , pp. 2753-2759
    • Sejbal, J.1    Klinot, J.2    Hrncirova, D.3    Vystrcil, A.4
  • 96
    • 0037518943 scopus 로고
    • Beckmann rearrangement of triterpene 3-ketoximes
    • Klinot, J.; Vystrcil, A. Beckmann rearrangement of triterpene 3-ketoximes. Collect. Czech. Chem. Commun. 1962, 27, 377-386.
    • (1962) Collect. Czech. Chem. Commun. , vol.27 , pp. 377-386
    • Klinot, J.1    Vystrcil, A.2
  • 97
    • 79953106550 scopus 로고
    • Dehydration of triterpenoid ring A e -lactams
    • Hase, T. Dehydration of triterpenoid ring A e -lactams. Acta Chem. Scand. 1970, 24, 364-365.
    • (1970) Acta Chem. Scand. , vol.24 , pp. 364-365
    • Hase, T.1
  • 98
    • 79953107164 scopus 로고
    • Aza triterpenes. II. A-Aza triterpenes of the lactones of methyl oleanonate and methyl betulonate
    • Rao, K.L.; Ramraj, S.K.; Sundararamaiah, T. Aza triterpenes. II. A-Aza triterpenes of the lactones of methyl oleanonate and methyl betulonate. J. Ind. Chem. Soc. 1980, 57, 833-834.
    • (1980) J. Ind. Chem. Soc. , vol.57 , pp. 833-834
    • Rao, K.L.1    Ramraj, S.K.2    Sundararamaiah, T.3
  • 99
    • 77951105186 scopus 로고    scopus 로고
    • Synthesis of acylhydrazones from lupane and 19β ,28-epoxy-18a- oleanane 2,3-seco-aldehydonitriles
    • Tolmacheva, I.A.; Galaiko, N.V.; Grishko, V.V. Synthesis of acylhydrazones from lupane and 19β ,28-epoxy-18a-oleanane 2,3-seco-aldehydonitriles. Chem. Nat. Comp. 2010, 46, 39-43.
    • (2010) Chem. Nat. Comp. , vol.46 , pp. 39-43
    • Tolmacheva, I.A.1    Galaiko, N.V.2    Grishko, V.V.3
  • 100
    • 77956358930 scopus 로고    scopus 로고
    • The synthesis of triterpenic amides on the basis of 2,3-seco-1-cyano- 19β ,28-epoxy-18a -olean-3-oic acid
    • Tolmacheva, I.A.; Igosheva, E.V.; Grishko, V.V.; Zhukova, O.S.; Gerasimova, G.K. The synthesis of triterpenic amides on the basis of 2,3-seco-1-cyano-19β ,28-epoxy-18a -olean-3-oic acid. Russ. J. Bioorg. Chem. 2010, 36, 377-382.
    • (2010) Russ. J. Bioorg. Chem. , vol.36 , pp. 377-382
    • Tolmacheva, I.A.1    Igosheva, E.V.2    Grishko, V.V.3    Zhukova, O.S.4    Gerasimova, G.K.5
  • 101
    • 7244255088 scopus 로고
    • Triterpenes. Part LXXXII. A-nor-derivatives of 19β,28-epoxy-18a- oleanane: Preparation and stereochemistry
    • Klinot, J.; Rozen, J.; Klinotova, E.; Vystrcil, A. Triterpenes. Part LXXXII. A-nor-derivatives of 19β,28-epoxy-18a-oleanane: preparation and stereochemistry. Collect. Czech. Chem. Commun. 1987, 52, 493-500.
    • (1987) Collect. Czech. Chem. Commun. , vol.52 , pp. 493-500
    • Klinot, J.1    Rozen, J.2    Klinotova, E.3    Vystrcil, A.4
  • 102
    • 34250564087 scopus 로고
    • Phytochemistry. V. Allobetulin
    • Dischendorfer, O.; Polak, O. Phytochemistry. V. Allobetulin. Monatsh. Chem. 1929, 51, 43-58.
    • (1929) Monatsh. Chem. , vol.51 , pp. 43-58
    • Dischendorfer, O.1    Polak, O.2
  • 103
    • 84982077822 scopus 로고
    • Polyterpenes and polyterpenoids. CVI. Oxidation of dihydrobetulinol and dihydrobetulonic acid with nitric acid
    • Ruzicka, L.; Isler, O. Polyterpenes, and polyterpenoids. CVI. Oxidation of dihydrobetulinol and dihydrobetulonic acid with nitric acid. Helv. Chim. Acta 1936, 19, 506-519.
    • (1936) Helv. Chim. Acta , vol.19 , pp. 506-519
    • Ruzicka, L.1    Isler, O.2
  • 106
    • 84982064397 scopus 로고
    • Polyterpenes and polyterpenoids. CXXIII. Degradation of allobetulin and hydroxymethyleneallobetulone with chromium trioxide
    • Ruzicka, L.; Govaert, F.; Goldberg, M.W.; Lamberton, A.H. Polyterpenes and polyterpenoids. CXXIII. Degradation of allobetulin and hydroxymethyleneallobetulone with chromium trioxide. Helv. Chim. Acta 1938, 21, 73-83.
    • (1938) Helv. Chim. Acta , vol.21 , pp. 73-83
    • Ruzicka, L.1    Govaert, F.2    Goldberg, M.W.3    Lamberton, A.H.4
  • 107
    • 0034340352 scopus 로고    scopus 로고
    • Preparation and Conformational Analysis of 1,2-Seco Derivatives of 19beta,28-Epoxy-18alpha-oleanane
    • DOI 10.1135/cccc20001339
    • Sejbal, J.; Homolova, M.; Tislerova, I.; Krecek, V. Preparation and conformational analysis of 1,2-seco derivatives of 19β,28-epoxy-18a- oleanane. Collect. Czech. Chem. Commun. 2000, 65, 1339-1356. (Pubitemid 33206488)
    • (2000) Collection of Czechoslovak Chemical Communications , vol.65 , Issue.8 , pp. 1339-1356
    • Sejbal, J.1    Homolova, M.2    Tislerova, I.3    Krecek, V.4
  • 108
    • 35548951411 scopus 로고    scopus 로고
    • Useful approach to access germanicanes from betulin
    • DOI 10.1016/j.tetlet.2007.09.171, PII S0040403907019661
    • Thibeault, D.; Legault, J.; Bouchard, J.; Pichette, A. Useful approach to access germanicanes from betulin. Tetrahedron Lett. 2007, 48, 8416-8419. (Pubitemid 350017832)
    • (2007) Tetrahedron Letters , vol.48 , Issue.48 , pp. 8416-8419
    • Thibeault, D.1    Legault, J.2    Bouchard, J.3    Pichette, A.4
  • 110
    • 77649098614 scopus 로고    scopus 로고
    • A one-step approach to the synthesis of germanicane triterpenoids from allobetulin
    • Kazakova, O.B.; Tolstikov, G.A.; Suponitskii, K.Y. A one-step approach to the synthesis of germanicane triterpenoids from allobetulin. Russ. J. Bioorg. Chem. 2010, 36, 133-135.
    • (2010) Russ. J. Bioorg. Chem. , vol.36 , pp. 133-135
    • Kazakova, O.B.1    Tolstikov, G.A.2    Suponitskii, K.Y.3
  • 113
    • 70549111588 scopus 로고    scopus 로고
    • Effects of lupane and oleanane Β- enaminoketones on the number and morphology of white blood cells
    • Anikina, L.V.; Tolmacheva, I.A.; Vikharev, Y.B.; Grisko, V.V. Effects of lupane and oleanane Β- enaminoketones on the number and morphology of white blood cells. Pharm. Chem. J. 2009, 43, 378-380.
    • (2009) Pharm. Chem. J. , vol.43 , pp. 378-380
    • Anikina, L.V.1    Tolmacheva, I.A.2    Vikharev, Y.B.3    Grisko, V.V.4
  • 114
    • 77956231045 scopus 로고    scopus 로고
    • Inhibitory effect of the natural product betulin and its derivatives against the intracellular bacterium Chlamydia pneumoniae
    • Salin, O.; Alakurtti, S.; Pohjala, L.; Siiskonen, A.; Maass, V.; Maass, M.; Yli-Kauhaluoma, J.; Vuorela, P. Inhibitory effect of the natural product betulin and its derivatives against the intracellular bacterium Chlamydia pneumoniae. Biochem. Pharmacol. 2010, 80, 1141-1151.
    • (2010) Biochem. Pharmacol. , vol.80 , pp. 1141-1151
    • Salin, O.1    Alakurtti, S.2    Pohjala, L.3    Siiskonen, A.4    Maass, V.5    Maass, M.6    Yli-Kauhaluoma, J.7    Vuorela, P.8


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