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Volumn 51, Issue , 2012, Pages 250-258

Synthesis and SAR studies of phenanthroindolizidine and phenanthroquinolizidine alkaloids as potent anti-tumor agents

Author keywords

14 Amino derivative; A549; Anti tumor activity; HL60; Phenanthroindolizidine; Phenanthroquinolizidine

Indexed keywords

ANTINEOPLASTIC AGENT; INDOLIZIDINE ALKALOID; PHENANTHRENE DERIVATIVE; QUINOLIZIDINE DERIVATIVE;

EID: 84862806711     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.02.048     Document Type: Article
Times cited : (47)

References (33)
  • 1
    • 0020054636 scopus 로고
    • The indolizidine alkaloids
    • DOI 10.1021/np50019a005
    • E. Gellert The indolizidine alkaloids J. Nat. Prod. 45 1982 50 73 (Pubitemid 12102893)
    • (1982) Journal of Natural Products , vol.45 , Issue.1 , pp. 50-73
    • Gellert, E.1
  • 2
    • 0034758814 scopus 로고    scopus 로고
    • Indolizidine and quinolizidine alkaloids
    • DOI 10.1039/b005384h
    • J.P. Michael Indolizidine and quinolizidine alkaloids Nat. Prod. Rep. 18 2001 520 542 (Pubitemid 33016992)
    • (2001) Natural Product Reports , vol.18 , Issue.5 , pp. 520-542
    • Michael, J.P.1
  • 3
    • 26844582966 scopus 로고    scopus 로고
    • Indolizidine and quinolizidine alkaloids
    • DOI 10.1039/b413748p
    • J.P. Michael Indolizidine and quinolizidine alkaloids Nat. Prod. Rep. 22 2005 603 626 (Pubitemid 41457417)
    • (2005) Natural Product Reports , vol.22 , Issue.5 , pp. 603-626
    • Michael, J.P.1
  • 4
    • 33947487426 scopus 로고
    • The antileukemia activity of tylocrebrine
    • E. Gellert, and R. Rudzats The antileukemia activity of tylocrebrine J. Med. Chem. 7 1964 361 362
    • (1964) J. Med. Chem. , vol.7 , pp. 361-362
    • Gellert, E.1    Rudzats, R.2
  • 5
    • 0017376831 scopus 로고
    • Mutants of CHO cells resistant to the protein synthesis inhibitors, cryptopleurine and tylocrebrine: genetic and biochemical evidence for common site of action of emetine, cryptopleurine, tylocrebrine, and tubulosine
    • R.S. Gupta, and L. Siminovitch Mutants of CHO cells resistant to the protein synthesis inhibitors, cryptopleurine and tylocrebrine: genetic and biochemical evidence for common site of action of emetine, cryptopleurine, tylocrebrine, and tubulosine Biochemistry 16 1977 3209 3214 (Pubitemid 8134434)
    • (1977) Biochemistry , vol.16 , Issue.14 , pp. 3209-3214
    • Gupta, R.S.1    Siminovitch, L.2
  • 7
    • 33845762339 scopus 로고    scopus 로고
    • Synthesis and structure-activity studies of antofine analogues as potential anticancer agents
    • DOI 10.1016/j.bmcl.2006.09.080, PII S0960894X06011437
    • Y. Fu, S.K. Lee, H.Y. Min, T. Lee, J. Lee, M. Cheng, and S. Kim Synthesis and structure-activity studies of antofine analogues as potential anticancer agents Bioorg. Med. Chem. Lett. 17 2007 97 100 (Pubitemid 46001584)
    • (2007) Bioorganic and Medicinal Chemistry Letters , vol.17 , Issue.1 , pp. 97-100
    • Fu, Y.1    Lee, S.K.2    Min, H.-Y.3    Lee, T.4    Lee, J.5    Cheng, M.6    Kim, S.7
  • 10
    • 33644845305 scopus 로고    scopus 로고
    • Anti-inflammatory mechanisms of phenanthroindolizidine alkaloids
    • C.W. Yang, W.L. Chen, P.L. Wu, H.Y. Tseng, and S.J. Lee Anti-inflammatory mechanisms of phenanthroindolizidine alkaloids Mol. Pharmacol. 69 2006 749 758
    • (2006) Mol. Pharmacol. , vol.69 , pp. 749-758
    • Yang, C.W.1    Chen, W.L.2    Wu, P.L.3    Tseng, H.Y.4    Lee, S.J.5
  • 13
    • 65749115131 scopus 로고    scopus 로고
    • Phenanthroindolizidines and phenanthroquinolizidines: Promising alkaloids for anti-cancer therapy
    • S.R. Chemler Phenanthroindolizidines and phenanthroquinolizidines: promising alkaloids for anti-cancer therapy Curr. Bioact. Compd. 5 2009 2 19
    • (2009) Curr. Bioact. Compd. , vol.5 , pp. 2-19
    • Chemler, S.R.1
  • 14
    • 0035210509 scopus 로고    scopus 로고
    • Isolation, total synthesis and biological activity of phenanthroindolizidine and phenanthroquinolizidine alkaloids
    • Z.G. Li, Z. Jin, and R.Q. Huang Synthesis and biological activity of phenanthroindolizidine and phenanthroquinolizidine alkaloids Synthesis 16 2001 2365 2378 (Pubitemid 33131974)
    • (2001) Synthesis , Issue.16 , pp. 2365-2378
    • Li, Z.1    Jin, Z.2    Huang, R.3
  • 15
    • 77955394316 scopus 로고
    • The pharmacological action of tylophorine: The alkaloid occurring in Tylophora asthmaticus
    • R.N.L.C. Chopra, N.N. De, and M. Chakerburty The pharmacological action of tylophorine: the alkaloid occurring in Tylophora asthmaticus Indian J. Med. Res. 23 1935 263 269
    • (1935) Indian J. Med. Res. , vol.23 , pp. 263-269
    • Chopra, R.N.L.C.1    De, N.N.2    Chakerburty, M.3
  • 18
    • 0014403406 scopus 로고
    • Inhibition of protein synthesis in ehrlich ascites-tumor cells by the phenanthrene alkaloids
    • G.R. Donaldson, M.R. Atkinson, and A.W. Murray Inhibition of protein synthesis in ehrlich ascites-tumor cells by the phenanthrene alkaloids Biochem. Biophys. Res. Commun. 31 1968 104 109
    • (1968) Biochem. Biophys. Res. Commun. , vol.31 , pp. 104-109
    • Donaldson, G.R.1    Atkinson, M.R.2    Murray, A.W.3
  • 19
    • 0015399428 scopus 로고
    • Mode of action of tylocrebrine: Effects on protein and nucleic acid synthesis
    • M.T. Huang, and A.P. Grollman Mode of action of tylocrebrine: effects on protein and nucleic acid synthesis Mol. Pharmacol. 8 1972 538 550
    • (1972) Mol. Pharmacol. , vol.8 , pp. 538-550
    • Huang, M.T.1    Grollman, A.P.2
  • 20
    • 1642475128 scopus 로고    scopus 로고
    • Novel Mode of Action of Tylophorine Analogs as Antitumor Compounds
    • DOI 10.1158/0008-5472.CAN-03-1904
    • W. Gao, W. Lam, S. Zhong, C. Kaczmarek, D.C. Baker, and Y.C. Cheng Novel mode of action of tylophorine analogs as antitumor compounds Cancer Res. 64 2004 678 688 (Pubitemid 38120910)
    • (2004) Cancer Research , vol.64 , Issue.2 , pp. 678-688
    • Gao, W.1    Lam, W.2    Zhong, S.3    Kaczmarek, C.4    Baker, D.C.5    Cheng, Y.-C.6
  • 21
    • 33750457941 scopus 로고    scopus 로고
    • Inhibition of cell growth and nuclear factor-κB activity in pancreatic cancer cell lines by a tylophorine analogue, DCB-3503
    • DOI 10.1158/1535-7163.MCT-06-0146
    • H.S. Shiah, W. Gao, D.C. Baker, and Y.C. Cheng Inhibition of cell growth and nuclear factor-κB activity in pancreatic cancer cell lines by a tylophorine analogue, DCB-3503 Mol. Cancer Ther. 5 2006 2484 2493 (Pubitemid 44650912)
    • (2006) Molecular Cancer Therapeutics , vol.5 , Issue.10 , pp. 2484-2493
    • Shiah, H.-S.1    Gao, W.2    Baker, D.C.3    Cheng, Y.-C.4
  • 22
    • 77956630631 scopus 로고    scopus 로고
    • Inhibition of cell growth and potentiation of tumor necrosis factor-α TNF-α-induced apoptosis by a phenanthroindolizidine alkaloid antofine in human colon cancer cells
    • H.Y. Min, H.J. Chung, E.H. Kim, S. Kim, E.J. Park, and S.K. Lee Inhibition of cell growth and potentiation of tumor necrosis factor-α TNF-α-induced apoptosis by a phenanthroindolizidine alkaloid antofine in human colon cancer cells Biochem. Pharmacol. 80 2010 1356 1364
    • (2010) Biochem. Pharmacol. , vol.80 , pp. 1356-1364
    • Min, H.Y.1    Chung, H.J.2    Kim, E.H.3    Kim, S.4    Park, E.J.5    Lee, S.K.6
  • 23
  • 24
    • 45649085396 scopus 로고    scopus 로고
    • Iron(III) chloride-based mild synthesis of phenanthrene and its application to total synthesis of phenanthroindolizidine alkaloids
    • K.L. Wang, M.Y. Lü, Q.M. Wang, and R.Q. Huang Iron(III) chloride-based mild synthesis of phenanthrene and its application to total synthesis of phenanthroindolizidine alkaloids Tetrahedron 64 2008 7504 7510
    • (2008) Tetrahedron , vol.64 , pp. 7504-7510
    • Wang, K.L.1    Lü, M.Y.2    Wang, Q.M.3    Huang, R.Q.4
  • 25
    • 77949782478 scopus 로고    scopus 로고
    • A simple and efficient oxidative coupling of aromatic nuclei mediated by manganese dioxide
    • K.L. Wang, Y.N. Hu, Z. Li, M. Wu, Z.H. Liu, B. Su, A. Yu, Y. Liu, and Q.M. Wang A simple and efficient oxidative coupling of aromatic nuclei mediated by manganese dioxide Synthesis 7 2010 1083 1090
    • (2010) Synthesis , vol.7 , pp. 1083-1090
    • Wang, K.L.1    Hu, Y.N.2    Li, Z.3    Wu, M.4    Liu, Z.H.5    Su, B.6    Yu, A.7    Liu, Y.8    Wang, Q.M.9
  • 27
    • 0021053335 scopus 로고
    • α-Amino acids as chiral educts for asymmetric products. Chirally specific syntheses of tylophorine and cryptopleurine
    • T.F. Buckley, and H. Rapoport Amino acids as chiral educts for asymmetric products. Chirally specific syntheses of tylophorine and cryptopleurine J. Org. Chem. 48 1983 4222 4232 (Pubitemid 14185236)
    • (1983) Journal of Organic Chemistry , vol.48 , Issue.23 , pp. 4222-4232
    • Buckley III, T.F.1    Rapoport, H.2
  • 28
    • 73349119635 scopus 로고    scopus 로고
    • Efficient and chirally specific synthesis of phenanthro-indolizidine alkaloids by Parham-type cycloacylation
    • Z.W. Wang, Z. Li, K.L. Wang, and Q.M. Wang Efficient and chirally specific synthesis of phenanthro-indolizidine alkaloids by Parham-type cycloacylation Eur. J. Org. Chem. 2 2010 292 299
    • (2010) Eur. J. Org. Chem. , vol.2 , pp. 292-299
    • Wang, Z.W.1    Li, Z.2    Wang, K.L.3    Wang, Q.M.4
  • 29
    • 78650148541 scopus 로고    scopus 로고
    • First total synthesis of (-)-and (+)-6-O-desmethylantofine
    • M. Wu, L. Li, B. Su, Z.H. Liu, and Q.M. Wang First total synthesis of (-)-and (+)-6-O-desmethylantofine Org. Biomol. Chem. 9 2011 141 145
    • (2011) Org. Biomol. Chem. , vol.9 , pp. 141-145
    • Wu, M.1    Li, L.2    Su, B.3    Liu, Z.H.4    Wang, Q.M.5
  • 30
    • 79952446433 scopus 로고    scopus 로고
    • The first and efficient synthesis of 14-aminophenanthro-indolizidine alkaloids
    • Z.W. Wang, L. Wang, and Q.M. Wang The first and efficient synthesis of 14-aminophenanthro-indolizidine alkaloids Synthesis 6 2011 979 983
    • (2011) Synthesis , vol.6 , pp. 979-983
    • Wang, Z.W.1    Wang, L.2    Wang, Q.M.3
  • 31
    • 75349102342 scopus 로고    scopus 로고
    • Highly efficient synthesis of phenanthroquinolizidine alkaloids via Parham-type cycliacylation
    • Z.W. Wang, and Q.M. Wang Highly efficient synthesis of phenanthroquinolizidine alkaloids via Parham-type cycliacylation Tetrahedron Lett. 10 2010 1377 1379
    • (2010) Tetrahedron Lett. , vol.10 , pp. 1377-1379
    • Wang, Z.W.1    Wang, Q.M.2
  • 32
    • 85011136029 scopus 로고
    • Studies on phenanthrene derivatives. IV. Syntheses of 2,3:5,6-bismethylenedioxy and 2,3:6,7-bismethylenedioxyphenanthrene and ultraviolet absorption spectra of certain methylenedioxyphenanthrenes
    • H. Shirai, and N. Oda Studies on phenanthrene derivatives. IV. Syntheses of 2,3:5,6-bismethylenedioxy and 2,3:6,7-bismethylenedioxyphenanthrene and ultraviolet absorption spectra of certain methylenedioxyphenanthrenes Chem. Pharm. Bull. 1 1962 31 37
    • (1962) Chem. Pharm. Bull. , vol.1 , pp. 31-37
    • Shirai, H.1    Oda, N.2
  • 33
    • 56149102126 scopus 로고    scopus 로고
    • Dihydroartemisinin induces apoptosis in HL-60 leukemia cells dependent of iron and p38 mitogen-activated protein kinase activation but independent of reactive oxygen species
    • J.J. Lu, L.H. Meng, Y.J. Cai, Q. Chen, L.J. Tong, L.P. Lin, and J. Ding Dihydroartemisinin induces apoptosis in HL-60 leukemia cells dependent of iron and p38 mitogen-activated protein kinase activation but independent of reactive oxygen species Cancer Biol. Ther. 7 2008 1017 1023
    • (2008) Cancer Biol. Ther. , vol.7 , pp. 1017-1023
    • Lu, J.J.1    Meng, L.H.2    Cai, Y.J.3    Chen, Q.4    Tong, L.J.5    Lin, L.P.6    Ding, J.7


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