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Volumn 101, Issue , 2015, Pages 391-399

Incorporation of a Michael acceptor enhances the antitumor activity of triterpenoic acids

Author keywords

Glycyrrhetinic acid; Oleanolic acid; Platantic acid; Triterpenoic acid; Tumor cells; Ursolic acid

Indexed keywords

ANTINEOPLASTIC AGENT; GLYCYRRHETINIC ACID DERIVATIVE; OLEANOLIC ACID DERIVATIVE; PLATANIC ACID DERIVATIVE; TRITERPENOIC ACID DERIVATIVE; TRITERPENOID; UNCLASSIFIED DRUG; URSOLIC ACID DERIVATIVE; TRITERPENE;

EID: 84936993133     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.07.004     Document Type: Article
Times cited : (43)

References (31)
  • 1
    • 84904635038 scopus 로고    scopus 로고
    • Betulinic acid and its derivatives: A patent review (2008-2013)
    • R. Csuk Betulinic acid and its derivatives: a patent review (2008-2013) Expert Opin. Ther. Pat. 24 2014 913 923
    • (2014) Expert Opin. Ther. Pat. , vol.24 , pp. 913-923
    • Csuk, R.1
  • 2
    • 0015947009 scopus 로고
    • Tumor inhibitors.1. Preliminary investigation of antitumor activity of Sarracenia-Flava
    • D.H. Miles, U. Kokpol, L.H. Zalkow, S.J. Steindel, and J.B. Nabors Tumor inhibitors.1. Preliminary investigation of antitumor activity of Sarracenia-Flava J. Pharm. Sci. 63 1974 613 615
    • (1974) J. Pharm. Sci. , vol.63 , pp. 613-615
    • Miles, D.H.1    Kokpol, U.2    Zalkow, L.H.3    Steindel, S.J.4    Nabors, J.B.5
  • 4
    • 38149032490 scopus 로고    scopus 로고
    • Pharmacological evaluation of C-3 modified Betulinic acid derivatives with potent anticancer activity
    • P. Rajendran, M. Jaggi, M.K. Singh, R. Mukherjee, and A.C. Burman Pharmacological evaluation of C-3 modified Betulinic acid derivatives with potent anticancer activity Invest. New. Drug 26 2008 25 34
    • (2008) Invest. New. Drug , vol.26 , pp. 25-34
    • Rajendran, P.1    Jaggi, M.2    Singh, M.K.3    Mukherjee, R.4    Burman, A.C.5
  • 6
    • 84939892720 scopus 로고    scopus 로고
    • Enhancement of anti-bacterial and anti-tumor activities of pentacyclic triterpenes by introducing exocyclic α,β-unsaturated ketone moiety in ring A
    • L.R. Huang, H. Luo, X.S. Yang, L. Chen, J.X. Zhang, D.P. Wang, and X.J. Hao Enhancement of anti-bacterial and anti-tumor activities of pentacyclic triterpenes by introducing exocyclic α,β-unsaturated ketone moiety in ring A Med. Chem. Res. 23 2014 4631 4641
    • (2014) Med. Chem. Res. , vol.23 , pp. 4631-4641
    • Huang, L.R.1    Luo, H.2    Yang, X.S.3    Chen, L.4    Zhang, J.X.5    Wang, D.P.6    Hao, X.J.7
  • 8
    • 34250712966 scopus 로고    scopus 로고
    • The synthesis of 18 beta-glycyrrhetinic acid derivatives which have increased antiproliferative and apoptotic effects in leukemia cells
    • D. Liu, D.D. Song, G. Guo, R. Wang, J.L. Lv, Y.K. Jing, and L.X. Zhao The synthesis of 18 beta-glycyrrhetinic acid derivatives which have increased antiproliferative and apoptotic effects in leukemia cells Bioorg. Med. Chem. 15 2007 5432 5439
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 5432-5439
    • Liu, D.1    Song, D.D.2    Guo, G.3    Wang, R.4    Lv, J.L.5    Jing, Y.K.6    Zhao, L.X.7
  • 9
    • 33644866837 scopus 로고    scopus 로고
    • Glycyrrhetic acid (a metabolic substance and aglycon of glycyrrhizin) induces apoptosis in human hepatoma, promyelotic leukemia and stomach cancer cells
    • H. Hibasami, H. Iwase, K. Yoshioka, and H. Takahashi Glycyrrhetic acid (a metabolic substance and aglycon of glycyrrhizin) induces apoptosis in human hepatoma, promyelotic leukemia and stomach cancer cells Int. J. Mol. Med. 17 2006 215 219
    • (2006) Int. J. Mol. Med. , vol.17 , pp. 215-219
    • Hibasami, H.1    Iwase, H.2    Yoshioka, K.3    Takahashi, H.4
  • 10
    • 52049126160 scopus 로고    scopus 로고
    • 18 beta-glycyrrhetinic acid induces apoptotic cell death in SiHa cells and exhibits a synergistic effect against antibiotic anti-cancer drug toxicity
    • C.S. Lee, Y.J. Kim, M.S. Lee, E.S. Han, and S.J. Lee 18 beta-glycyrrhetinic acid induces apoptotic cell death in SiHa cells and exhibits a synergistic effect against antibiotic anti-cancer drug toxicity Life Sci. 83 2008 481 489
    • (2008) Life Sci. , vol.83 , pp. 481-489
    • Lee, C.S.1    Kim, Y.J.2    Lee, M.S.3    Han, E.S.4    Lee, S.J.5
  • 12
    • 84911447201 scopus 로고    scopus 로고
    • Recent developments in the synthesis of antitumor-active glycyrrhetinic acid derivatives
    • R. Csuk Recent developments in the synthesis of antitumor-active glycyrrhetinic acid derivatives Mini Rev. Org. Chem. 11 2014 253 261
    • (2014) Mini Rev. Org. Chem. , vol.11 , pp. 253-261
    • Csuk, R.1
  • 13
    • 77958003690 scopus 로고    scopus 로고
    • Synthesis and antitumour activity of glycyrrhetinic acid derivatives
    • S. Schwarz, and R. Csuk Synthesis and antitumour activity of glycyrrhetinic acid derivatives Bioorg. Med. Chem. 18 2010 7458 7474
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 7458-7474
    • Schwarz, S.1    Csuk, R.2
  • 15
    • 84861327779 scopus 로고    scopus 로고
    • Electrophilic natural products and their biological targets
    • M. Gersch, J. Kreuzer, and S.A. Sieber Electrophilic natural products and their biological targets Nat. Prod. Rep. 29 2012 659 682
    • (2012) Nat. Prod. Rep. , vol.29 , pp. 659-682
    • Gersch, M.1    Kreuzer, J.2    Sieber, S.A.3
  • 16
    • 0026689383 scopus 로고
    • Glycyrrhetinic acid derivatives as potent inhibitors of Na+-, K+-ATPase. Synthesis and structure-activity relationships
    • T. Terasawa, T. Okada, T. Hara, and K. Itoh Glycyrrhetinic acid derivatives as potent inhibitors of Na+-, K+-ATPase. Synthesis and structure-activity relationships Eur. J. Med. Chem. 27 1992 345 351
    • (1992) Eur. J. Med. Chem. , vol.27 , pp. 345-351
    • Terasawa, T.1    Okada, T.2    Hara, T.3    Itoh, K.4
  • 17
    • 84861628814 scopus 로고    scopus 로고
    • Alkylidene branched lupane derivatives: Synthesis and antitumor activity
    • R. Csuk, S. Stark, C. Nitsche, A. Barthel, and B. Siewert Alkylidene branched lupane derivatives: synthesis and antitumor activity Eur. J. Med. Chem. 53 2012 337 345
    • (2012) Eur. J. Med. Chem. , vol.53 , pp. 337-345
    • Csuk, R.1    Stark, S.2    Nitsche, C.3    Barthel, A.4    Siewert, B.5
  • 18
    • 32644444553 scopus 로고
    • Synthesis of 4α-methyl-Δ7-steroids. The interrelation of cholesterol, citrostadienol, and lophenol
    • Y. Mazur, and F. Sondheimer Synthesis of 4α-methyl-Δ7-steroids. The interrelation of cholesterol, citrostadienol, and lophenol J. Am. Chem. Soc. 80 1958 6296 6299
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 6296-6299
    • Mazur, Y.1    Sondheimer, F.2
  • 19
    • 67649404704 scopus 로고    scopus 로고
    • A mild and efficient bisaldolization of ketones and its application towards spirocyclic 1,3-dioxanes and novel 1,3,5-trioxocanes
    • N. Srinivas, V.K. Marrapu, and K. Bhandari A mild and efficient bisaldolization of ketones and its application towards spirocyclic 1,3-dioxanes and novel 1,3,5-trioxocanes Synlett 2009 1346 1350
    • (2009) Synlett , pp. 1346-1350
    • Srinivas, N.1    Marrapu, V.K.2    Bhandari, K.3
  • 22
    • 84890816801 scopus 로고    scopus 로고
    • The chemical and biological potential of C ring modified triterpenoids
    • B. Siewert, J. Wiemann, A. Köwitsch, and R. Csuk The chemical and biological potential of C ring modified triterpenoids Eur. J. Med. Chem. 72 2014 84 101
    • (2014) Eur. J. Med. Chem. , vol.72 , pp. 84-101
    • Siewert, B.1    Wiemann, J.2    Köwitsch, A.3    Csuk, R.4
  • 23
    • 80054924524 scopus 로고    scopus 로고
    • Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives
    • R. Csuk, S. Schwarz, B. Siewert, R. Kluge, and D. Ströhl Synthesis and antitumor activity of ring A modified glycyrrhetinic acid derivatives Eur. J. Med. Chem. 46 2011 5356 5369
    • (2011) Eur. J. Med. Chem. , vol.46 , pp. 5356-5369
    • Csuk, R.1    Schwarz, S.2    Siewert, B.3    Kluge, R.4    Ströhl, D.5
  • 24
    • 4544277618 scopus 로고    scopus 로고
    • Design, synthesis, and biological evaluation of biotin conjugates of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid for the isolation of the protein targets
    • T. Honda, T. Janosik, Y. Honda, J. Han, K.T. Liby, C.R. Williams, R.D. Couch, A.C. Anderson, M.B. Sporn, and G.W. Gribble Design, synthesis, and biological evaluation of biotin conjugates of 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid for the isolation of the protein targets J. Med. Chem. 47 2004 4923 4932
    • (2004) J. Med. Chem. , vol.47 , pp. 4923-4932
    • Honda, T.1    Janosik, T.2    Honda, Y.3    Han, J.4    Liby, K.T.5    Williams, C.R.6    Couch, R.D.7    Anderson, A.C.8    Sporn, M.B.9    Gribble, G.W.10
  • 25
    • 79956339740 scopus 로고    scopus 로고
    • Synthesis and antitumor activity of ring a-modified glycyrrhetinic acid derivatives
    • R. Csuk, S. Schwarz, B. Siewert, R. Kluge, and D. Ströhl Synthesis and antitumor activity of ring a-modified glycyrrhetinic acid derivatives Z. Naturforsch. B 66 2011 521 532
    • (2011) Z. Naturforsch. B , vol.66 , pp. 521-532
    • Csuk, R.1    Schwarz, S.2    Siewert, B.3    Kluge, R.4    Ströhl, D.5
  • 26
    • 0010837418 scopus 로고
    • Triterpenes. IX. The triterpenes from the bark of Sam-bucus nigra and the preparation of 3-eipursolic acid
    • S. Huneck, and G. Snatzke Triterpenes. IX. The triterpenes from the bark of Sam-bucus nigra and the preparation of 3-eipursolic acid Chem. Ber. 98 1965 120 125
    • (1965) Chem. Ber. , vol.98 , pp. 120-125
    • Huneck, S.1    Snatzke, G.2
  • 27
    • 2442684055 scopus 로고
    • Chemistry of triterpenes and related compounds. XXXVIII. Acidic constituents of dammar resin
    • S. Brewis, and T.G. Halsall Chemistry of triterpenes and related compounds. XXXVIII. Acidic constituents of dammar resin J. Chem. Soc. 1961 646 650
    • (1961) J. Chem. Soc. , pp. 646-650
    • Brewis, S.1    Halsall, T.G.2
  • 28
    • 34247557958 scopus 로고    scopus 로고
    • Remote hydroxylation of methyl groups by regioselective cyclopalladation. Partial synthesis of hyptatic acid-A
    • A. Garcia-Granados, P.E. Lopez, E. Melguizo, A. Parra, and Y. Simeo Remote hydroxylation of methyl groups by regioselective cyclopalladation. Partial synthesis of hyptatic acid-A J. Org. Chem. 72 2007 3500 3509
    • (2007) J. Org. Chem. , vol.72 , pp. 3500-3509
    • Garcia-Granados, A.1    Lopez, P.E.2    Melguizo, E.3    Parra, A.4    Simeo, Y.5
  • 29
    • 0000820093 scopus 로고
    • Triterpenes. IV. Triterpene acids of Liquidambar orientalis
    • S. Huneck Triterpenes. IV. Triterpene acids of Liquidambar orientalis Tetrahedron 19 1963 479 482
    • (1963) Tetrahedron , vol.19 , pp. 479-482
    • Huneck, S.1
  • 30
    • 84892711975 scopus 로고    scopus 로고
    • Membrane damaging activity of a maslinic acid analog
    • B. Siewert, and R. Csuk Membrane damaging activity of a maslinic acid analog Eur. J. Med. Chem. 74 2014 1 6
    • (2014) Eur. J. Med. Chem. , vol.74 , pp. 1-6
    • Siewert, B.1    Csuk, R.2
  • 31
    • 84891481757 scopus 로고    scopus 로고
    • Towards cytotoxic and selective derivatives of maslinic acid
    • B. Siewert, E. Pianowski, A. Obernauer, and R. Csuk Towards cytotoxic and selective derivatives of maslinic acid Bioorg. Med. Chem. 22 2014 594 615
    • (2014) Bioorg. Med. Chem. , vol.22 , pp. 594-615
    • Siewert, B.1    Pianowski, E.2    Obernauer, A.3    Csuk, R.4


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