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Volumn 19, Issue 6, 2014, Pages 7881-7900

Synthesis and cytotoxic activity of a new group of heterocyclic analogues of the combretastatins

Author keywords

Combretastatins; Cytotoxicity; Furocoumarins; Oreoselone; Psoralen; Semi hydrogenation; Sonogashira coupling

Indexed keywords

ANTINEOPLASTIC AGENT; BIBENZYL DERIVATIVE; COMBRETASTATIN; COMBRETASTATIN A4 PHOSPHATE; COUMARIN DERIVATIVE; FUROCOUMARIN DERIVATIVE; OREOSELONE; PSORALEN; STILBENE DERIVATIVE; TUBULIN MODULATOR;

EID: 84903308306     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules19067881     Document Type: Article
Times cited : (16)

References (37)
  • 1
    • 0023217561 scopus 로고
    • Antineoplastic agents 122. Constituents of combretum caffrum
    • Pettit, G.R.; Cragg, G.M.; Singh, S.B. Antineoplastic agents, 122. Constituents of Combretum caffrum. J. Nat. Prod. 1987, 50, 386-391.
    • (1987) J. Nat. Prod. , vol.50 , pp. 386-391
    • Pettit, G.R.1    Cragg, G.M.2    Singh, S.B.3
  • 2
    • 0024427745 scopus 로고
    • Antimitotic natural products combretastatin A-4 and combretastatin A-2: Studies on the mechanism of the ir inhibition of the binding of colchicine to tubulin
    • Lin, C.M.; Ho, H.H.; Pettit, G.R.; Hamel, E. Antimitotic natural products combretastatin A-4 and combretastatin A-2: Studies on the mechanism of the ir inhibition of the binding of colchicine to tubulin. Biochemistry 1989, 28, 6984-6991.
    • (1989) Biochemistry , vol.28 , pp. 6984-6991
    • Lin, C.M.1    Ho, H.H.2    Pettit, G.R.3    Hamel, E.4
  • 4
    • 84882963376 scopus 로고    scopus 로고
    • Small molecule sequential dual-targeting theragnostic strategy (smsdtts): From preclinical experiments towards possible clinical anticancer applications
    • Li, J.; Oyen, R.; Verbruggen, A.; Ni, Y. Small Molecule Sequential Dual-Targeting Theragnostic Strategy (SMSDTTS): From Preclinical Experiments towards Possible Clinical Anticancer Applications. J. Cancer 2013, 4, 133-145.
    • (2013) J. Cancer , vol.4 , pp. 133-145
    • Li, J.1    Oyen, R.2    Verbruggen, A.3    Ni, Y.4
  • 5
    • 79960006369 scopus 로고    scopus 로고
    • Biological potential and structure-activity relationships of most recently developed vascular disrupting agents: A n overview of new derivatives of natural combretastatin A-4
    • Marrelli, M.; Conforti, F.; Statti, G.A.; Cachet, X.; Michel, S.; Tillequin F.; Menichini, F. Biological potential and structure-activity relationships of most recently developed vascular disrupting agents: A n overview of new derivatives of natural combretastatin A-4. Curr. Med. Chem. 2011, 18, 3035-3081.
    • (2011) Curr. Med. Chem. , vol.18 , pp. 3035-3081
    • Marrelli, M.1    Conforti, F.2    Statti, G.A.3    Cachet, X.4    Michel, S.5    Tillequin, F.6    Menichini, F.7
  • 8
    • 54149093135 scopus 로고    scopus 로고
    • Antineoplastic agents.552. Oxidation of combretastatin A-1: Trapping the o-quinone intermediate considered the metabolic product of the corresponding phosphate prodrug
    • Pettit, G.R.; Thornhill, A.J.; Mo ser, B.R.; Hogan, F. Antineoplastic Agents. 552. Oxidation of Combretastatin A-1: Trapping the o-quinone intermediate considered the metabolic product of the corresponding phosphate prodrug. J. Nat. Prod. 2008, 71, 1561-1563.
    • (2008) J. Nat. Prod. , vol.71 , pp. 1561-1563
    • Pettit, G.R.1    Thornhill, A.J.2    Moser, B.R.3    Hogan, F.4
  • 12
    • 84873410816 scopus 로고    scopus 로고
    • Synthesis of (Z) isomers of benzoheterocyclic deri vatives of combretastatin A-4: A comparative study of several methods
    • Nguyen, T.T.B.; Lomberget, T.; Tran, N.C.; Barret, R. Synthesis of (Z) isomers of benzoheterocyclic deri vatives of combretastatin A-4: A comparative study of several methods. Tetrahedron 2013, 69, 2336-2347.
    • (2013) Tetrahedron , vol.69 , pp. 2336-2347
    • Nguyen, T.T.B.1    Lomberget, T.2    Tran, N.C.3    Barret, R.4
  • 13
    • 8844219683 scopus 로고    scopus 로고
    • Furocoumarins in me dicinal chemistry: Synthesis, natural occurrence and biological activity
    • Santana L.; Uriarte, E.; Roleira, F.; Milhazes, N.; Borges, F. Furocoumarins in me dicinal chemistry: Synthesis, natural occurrence and biological activity. Curr. Med. Chem. 2004, 11, 3239-3261.
    • (2004) Curr. Med. Chem. , vol.11 , pp. 3239-3261
    • Santana, L.1    Uriarte, E.2    Roleira, F.3    Milhazes, N.4    Borges, F.5
  • 14
    • 70450162772 scopus 로고    scopus 로고
    • The structure and pharmacological functions of coumarins and their derivatives
    • Wu L.,Wang X.,Xu W.,Farzaneh F.,Xu R. The structure and pharmacological functions of coumarins and their derivatives, Curr. Med. Chem., 2009,16, 4236-4260.
    • (2009) Curr. Med. Chem. , vol.16 , pp. 4236-4260
    • Wu, L.1    Wang, X.2    Xu, W.3    Farzaneh, F.4    Xu, R.5
  • 16
    • 38649102191 scopus 로고    scopus 로고
    • Induction of α-globin mRNA, erythroid differentiation and apoptosis in UVA-irradiated human erythroid cells in the presence of furocoumarin derivatives
    • Viola, G.; Vedaldi, D.; Dall ?Acqua, F.; Fortunato, E.; Basso, G.; Bianchi, N.; Zuccato, C.; Borgatti, M.; Lampronti, I.; Gambari, R. Induction of α-globin mRNA, erythroid differentiation and apoptosis in UVA-irradiated human erythroid cells in the presence of furocoumarin derivatives. Biochem. Pharmacol. 2008, 2, 810-825.
    • (2008) Biochem. Pharmacol. , vol.2 , pp. 810-825
    • Viola, G.1    Vedaldi, D.2    Dallacqua, F.3    Fortunato, E.4    Basso, G.5    Bianchi, N.6    Zuccato, C.7    Borgatti, M.8    Lampronti, I.9    Gambari, R.10
  • 20
  • 21
    • 0032858830 scopus 로고    scopus 로고
    • The synthesis of (e) and (z)-combretastatins a-4 and a phenanthrene from combretum caffrum
    • Lawrence, N.J.; Ghani, F.A.; Hepworth, L.A.; Hadfield, J.A .; McGown, A.T.; Pritchard, R.G. The Synthesis of (E) and (Z)-Combretastatins A-4 and a Phenanthrene from Combretum caffrum. Synthesis 1999, 1656-1660.
    • (1999) Synthesis , pp. 1656-1660
    • Lawrence, N.J.1    Ghani, F.A.2    Hepworth, L.A.3
  • 22
    • 34548299900 scopus 로고    scopus 로고
    • A new synthesis of combretastatins A-4 and AVE-8062A
    • Lara-Ochoa, F.; Espinosa-Pé rez, G. A new synthesis of combretastatins A-4 and AVE-8062A. Tetrahedron Lett. 2007, 48, 7007-7010.
    • (2007) Tetrahedron Lett. , vol.48 , pp. 7007-7010
    • Lara-Ochoa, F.1    Espinosa-Pérez, G.2
  • 23
    • 80755132238 scopus 로고    scopus 로고
    • New efficient synthesis of combretastatin a-4 via colvin rearrangement
    • Petrov, O.I.; Gerova, M.S.; Chanev, C.D.; Petrova, K.V. New Efficient Synthesis of Combretastatin A-4 via Colvin Rearrangement. Synthesis 2011, 3711-3715.
    • (2011) Synthesis , pp. 3711-3715
    • Petrov, O.I.1    Gerova, M.S.2    Chanev, C.D.3    Petrova, K.V.4
  • 26
    • 84901941630 scopus 로고    scopus 로고
    • Synthesis of (Z)-styrylfurocoumarins as the heterocyclic analogues of combretastatins
    • Lipeeva, A.V.; Shul? ts, E.E.; Shakirov, M.M.; Tolstikov, G.A. Synthesis of (Z)-styrylfurocoumarins as the heterocyclic analogues of combretastatins. Dokl. Chem. 2012, 447, 282-285.
    • (2012) Dokl. Chem. , vol.447 , pp. 282-285
    • Lipeeva, A.V.1    Shults, E.E.2    Shakirov, M.M.3    Tolstikov, G.A.4
  • 27
    • 0025294320 scopus 로고
    • A feasibility study of the MTT assay for chemosensitivity test ing in ovarian malignancy
    • Wilson, J.K.; Sargent, J.M.; Elgie, A.W.; Hill, J.G.; Taylor, C.G. A feasibility study of the MTT assay for chemosensitivity test ing in ovarian malignancy. Br. J. Cancer 1990, 62, 189-194.
    • (1990) Br. J. Cancer , vol.62 , pp. 189-194
    • Wilson, J.K.1    Sargent, J.M.2    Elgie, A.W.3    Hill, J.G.4    Taylor, C.G.5
  • 29
    • 0141518578 scopus 로고    scopus 로고
    • Stru ctural requirements for the interreaction of combretastatins with tubulin: How important is the trimethoxy uniti
    • Gaukroger, K.; Hadfield, J.A.; Lawrence, N.J.; Nolan, S.; McGown, A.T. Stru ctural requirements for the interreaction of combretastatins with tubulin: How important is the trimethoxy uniti Org. Biomol. Chem. 2003, 1, 3033-3037.
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 3033-3037
    • Gaukroger, K.1    Hadfield, J.A.2    Lawrence, N.J.3    Nolan, S.4    McGown, A.T.5
  • 32
    • 43049130754 scopus 로고    scopus 로고
    • 1,5-Disubstituted 1,2,3-triazoles as cis-restricted analogues of combretastatin A-4: Synthesis, molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin
    • Odlo, K.; Hentzen, J.; Fournier dit Chabert, J.; Ducki, S.; Gani, O.A.; Sylte, I.; Skrede, M.; Flören es, V.A.; Hansen, T.V. 1,5-Disubstituted 1,2,3-triazoles as cis-restricted analogues of combretastatin A-4: Synthesis, molecular modeling and evaluation as cytotoxic agents and inhibitors of tubulin. Bioorg. Med. Chem. 2008, 16, 4829-4838.
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 4829-4838
    • Odlo, K.1    Hentzen, J.2    Fournierdit Chabert, J.3    Ducki, S.4    Gani, O.A.5    Sylte, I.6    Skrede, M.7    Flörenes, V.A.8    Hansen, T.V.9
  • 33
    • 0003160578 scopus 로고    scopus 로고
    • A new preparation of benzofurans utilizing trimethylsilyl-diazomethane
    • Ito, Y.; Aoyama, T.; Shioiri, T. A new preparation of benzofurans utilizing trimethylsilyl-diazomethane. Synlett 1997, 1163-1164.
    • (1997) Synlett , pp. 1163-1164
    • Ito, Y.1    Aoyama, T.2    Shioiri, T.3
  • 34
    • 79959945184 scopus 로고    scopus 로고
    • 2-Amino-4-methyl-5-phenylethyl substituted-7-N-benzylpyrrolo[2,3-d] pyrimidines as novel antitumor antimitotic agents that also reverse tumor resistance
    • Gangjee, A.; Namjoshi, O.A.; Keller, S.N.; Smith, C.D. 2-Amino-4-methyl-5-phenylethyl substituted-7-N-benzylpyrrolo[2,3-d]pyrimidines as novel antitumor antimitotic agents that also reverse tumor resistance. Bioorg . Med. Chem. 2011, 19, 4355-4365.
    • (2011) Bioorg . Med. Chem. , vol.19 , pp. 4355-4365
    • Gangjee, A.1    Namjoshi, O.A.2    Keller, S.N.3    Smith, C.D.4
  • 35
    • 79957444475 scopus 로고    scopus 로고
    • Simple and improved regioselective brominations of aromatic compounds using N-benzyl-N,N-dimethylanilinium peroxo disulfate in the presence of potassium bromide under mild reaction conditions
    • Ghasemnejad-Bosra, H.; Ramzanian-Lehmali, F.; Jafari, S. Simple and improved regioselective brominations of aromatic compounds using N-benzyl-N,N-dimethylanilinium peroxo disulfate in the presence of potassium bromide under mild reaction conditions. J. Serb. Chem. Soc. 2011, 76, 685-692.
    • (2011) J. Serb. Chem. Soc. , vol.76 , pp. 685-692
    • Ghasemnejad-Bosra, H.1    Ramzanian-Lehmali, F.2    Jafari, S.3
  • 36
    • 77954702899 scopus 로고    scopus 로고
    • Single bifunctional ru thenium catalyst for one-pot cyclization and hydration giving functionalized indoles and benzofurans
    • Nair R.N.,Lee P.J.,Grotjahn D.B.,Rheingold A.L. Single bifunctional ru thenium catalyst for one-pot cyclization and hydration giving functionalized indoles and benzofurans, Chem. Eur. J.,2010, 16, 7992-7995.
    • (2010) Chem. Eur. J. , vol.16 , pp. 7992-7995
    • Nair, R.N.1    Lee, P.J.2    Grotjahn, D.B.3    Rheingold, A.L.4
  • 37
    • 33846981133 scopus 로고    scopus 로고
    • Bromination of some aromatic compounds with potassium bromide in the presence of benzyltriphenylphosphonium peroxodisulfate
    • Tajik, H.; Mohammadpoor-Baltork, I.; Albadi, J. Bromination of some aromatic compounds with potassium bromide in the presence of benzyltriphenylphosphonium peroxodisulfate. Synth. Commun. 2007, 37, 323-328.
    • (2007) Synth. Commun. , vol.37 , pp. 323-328
    • Tajik, H.1    Mohammadpoor-Baltork, I.2    Albadi, J.3


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