메뉴 건너뛰기




Volumn 87, Issue , 2014, Pages 46-53

Synthesis, cytotoxic effects and tubulin polymerization inhibition of 1,4-disubstituted 1,2,3-triazole analogs of 2-methoxyestradiol

Author keywords

1,2,3 Triazoles; 2 Methoxyestradiol; Anti cancer; Cytotoxicity; Estrogens; Tubulin inhibition

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 2 METHOXYESTRA 17 [1 (3,4,5 TRIMETHOXYBENZYL) 1H 1,2, 3 TRIAZOL 4 YL)DIOL; 2 METHOXYESTRA 17 [1 (3,4,5 TRIMETHOXYPHENYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 2 METHOXYESTRA 17 [1 (4 BROMOPHENYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 2 METHOXYESTRA 17 [1 (4 CHLOROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 2 METHOXYESTRA 17 [1 (4 FLOUROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 2 METHOXYESTRA 17 [1 (4 HYDROXYPHENYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 2 METHOXYESTRA 17 [1 (4 METHOXYPHENYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 2 METHOXYESTRA 17 [1 PHENYL 1H 1,2,3 TRIAZOL 4 YL]DIOL; 2 METHOXYESTRA 17 [1 [4 (TERT BUTYL)PHENYL] 1H 1,2,3 TRIAZOL 4 YL]DIOL; 2 METHOXYESTRA 17 [1 [4 (TRIFLUOROMETHOXYL)PHENYL] 1H 1,2, 3 TRIAZOL 4 YL]DIOL; 2 METHOXYESTRA 17 [1 [4 (TRIFLUOROMETHYL)PHENYL] 1H 1,2,3 TRIAZOL 4 YL)DIOL; 2 METHOXYESTRA 17 [1 [4 METHYLPHENYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 2 METHOXYESTRADIOL; 3 TERT BUTYLDIMETHYLSILOXY 2 METHOXYESTRA 17 (1 PHENYL 1H 1,2,3 TRIAZOL 4 YL)DIOL; 3 TERT BUTYLDIMETHYLSILOXY 2 METHOXYESTRA 17 [1 (3,4,5 TRIMETHOXYBENZYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 3 TERT BUTYLDIMETHYLSILOXY 2 METHOXYESTRA 17 [1 (3,4,5 TRIMETHOXYPHENYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 3 TERT BUTYLDIMETHYLSILOXY 2 METHOXYESTRA 17 [1 (4 BROMOPHENYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 3 TERT BUTYLDIMETHYLSILOXY 2 METHOXYESTRA 17 [1 (4 CHLOROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 3 TERT BUTYLDIMETHYLSILOXY 2 METHOXYESTRA 17 [1 (4 FLOUROPHENYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 3 TERT BUTYLDIMETHYLSILOXY 2 METHOXYESTRA 17 [1 (4 HYDROXYPHENYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 3 TERT BUTYLDIMETHYLSILOXY 2 METHOXYESTRA 17 [1 (4 METHOXYBENZYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 3 TERT BUTYLDIMETHYLSILOXY 2 METHOXYESTRA 17 [1 (4 METHOXYPHENYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; 3 TERT BUTYLDIMETHYLSILOXY 2 METHOXYESTRA 17 [1 [4 (TERT BUTYL)PHENYL] 1H 1,2,3 TRIAZOL 4 YL]DIOL; 3 TERT BUTYLDIMETHYLSILOXY 2 METHOXYESTRA 17 [1 [4 (TRIFLUOROMETHOXYL)PHENYL] 1H 1,2,3 TRIAZOL 4 YL]DIOL; 3 TERT BUTYLDIMETHYLSILOXY 2 METHOXYESTRA 17 [1 [4 (TRIFLUOROMETHYL)PHENYL] 1H 1,2,3 TRIAZOL 4 YL]DIOL; ANTINEOPLASTIC AGENT; METHOXYESTRA 17 [1 (4 METHOXYBENZYL) 1H 1,2,3 TRIAZOL 4 YL]DIOL; TUBULIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; 2-METHOXYESTRADIOL; ESTRADIOL; TRIAZOLE DERIVATIVE; TUBULIN MODULATOR;

EID: 84902649683     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2014.05.020     Document Type: Article
Times cited : (27)

References (31)
  • 1
    • 84886727811 scopus 로고    scopus 로고
    • Current status on development of steroids as anticancer agents
    • A. Gupta, B.S. Kumar, and A.S. Negi Current status on development of steroids as anticancer agents J Steroid Biochem Mol Biol 137 2013 2242 2270
    • (2013) J Steroid Biochem Mol Biol , vol.137 , pp. 2242-2270
    • Gupta, A.1    Kumar, B.S.2    Negi, A.S.3
  • 3
    • 4243640918 scopus 로고
    • Metabolic fate of catechol estrogens
    • G.R. Merriam, M.B. Lipsett, Raven Press New York
    • C.P. Martucci Metabolic fate of catechol estrogens G.R. Merriam, M.B. Lipsett, Catechol estrogens 1983 Raven Press New York 115 121
    • (1983) Catechol Estrogens , pp. 115-121
    • Martucci, C.P.1
  • 5
    • 0028220858 scopus 로고
    • The endogenous oestrogen metabolite 2-methoxyoestradiol inhibits angiogenesis and suppresses tumour growth
    • DOI 10.1038/368237a0
    • T. Fotsis, Y. Zhang, M.S. Pepper, H. Adlercreutz, R. Montesano, and P.P. Nawroth et al. The endogenous estrogen metabolite 2-methoxyoestradiol inhibits angiogenesis and suppresses tumour growth Nature 268 1994 237 239 (Pubitemid 24108838)
    • (1994) Nature , vol.368 , Issue.6468 , pp. 237-239
    • Fotsis, T.1    Zhang, Y.2    Pepper, M.S.3    Adlercreutz, H.4    Montesano, R.5    Nawrotht, P.P.6    Schweigerer, L.7
  • 6
    • 78649948637 scopus 로고    scopus 로고
    • Therapeutic promises of 2-methoxyestradiol and its drug disposition challenges
    • S. Verenich, and P.M. Gerk Therapeutic promises of 2-methoxyestradiol and its drug disposition challenges Mol Pharm 7 2010 2030 2039
    • (2010) Mol Pharm , vol.7 , pp. 2030-2039
    • Verenich, S.1    Gerk, P.M.2
  • 7
    • 84866684482 scopus 로고    scopus 로고
    • Synthetic 2-methoxyestradiol derivatives: Structure-activity relationships
    • J.F. Peyrat, J.D. Brion, and M. Alami Synthetic 2-methoxyestradiol derivatives: structure-activity relationships Curr Med Chem 19 2012 4142 4156
    • (2012) Curr Med Chem , vol.19 , pp. 4142-4156
    • Peyrat, J.F.1    Brion, J.D.2    Alami, M.3
  • 9
    • 0037032474 scopus 로고    scopus 로고
    • Mechanisms for 2-methoxyestradiol-induced apoptosis of prostate cancer cells
    • DOI 10.1016/S0014-5793(02)03478-6, PII S0014579302034786
    • S. Bu, A. Blaukat, X. Fu, N.E. Heldin, and M. Landstrom Mechanisms for 2-methoxyestradiol-induced apoptosis of prostate cancer cells FEBS Lett 531 2002 141 151 (Pubitemid 35341185)
    • (2002) FEBS Letters , vol.531 , Issue.2 , pp. 141-151
    • Bu, S.1    Blaukat, A.2    Fu, X.3    Heldin, N.-E.4    Landstrom, M.5
  • 10
    • 0042731370 scopus 로고    scopus 로고
    • Angiostatic treatment of neuroblastoma
    • E. Wassberg Angiostatic treatment of neuroblastoma Ups J Med Chem Sci 104 1999 1 24
    • (1999) Ups J Med Chem Sci , vol.104 , pp. 1-24
    • Wassberg, E.1
  • 11
    • 0842269204 scopus 로고    scopus 로고
    • Mechanism of action of 2-methoxyestradiol: New developments
    • DOI 10.1016/j.drup.2003.10.001
    • S.L. Mooberry Mechanism of action of 2-methoxyestradiol: new developments Drug Resist Updates 6 2003 355 361 (Pubitemid 38173586)
    • (2003) Drug Resistance Updates , vol.6 , Issue.6 , pp. 355-361
    • Mooberry, S.L.1
  • 12
    • 25144452785 scopus 로고    scopus 로고
    • A phase II multicenter, randomized, double-blind, safety trial assessing the pharmacokinetics, pharmacodynamics, and efficacy of oral 2-methoxyestradiol capsules in hormone-refractory prostate cancer
    • DOI 10.1158/1078-0432.CCR-05-0440
    • C. Sweeney, G. Liu, C. Yiannoutsos, J. Kolesar, D. Horvath, and M.J. Staab et al. A phase II multicenter, randomized, double-blind, safety trial assessing the pharmacokinetics, pharmacodynamics, and efficacy of oral 2-methoxyestradiol capsules in hormone-refractory prostate cancer Clin Cancer Res 11 2005 6625 6633 (Pubitemid 41339003)
    • (2005) Clinical Cancer Research , vol.11 , Issue.18 , pp. 6625-6633
    • Sweeney, C.1    Liu, G.2    Yiannoutsos, C.3    Kolesar, J.4    Horvath, D.5    Staab, M.J.6    Fife, K.7    Armstrong, V.8    Treston, A.9    Sidor, C.10    Wilding, G.11
  • 14
    • 33750483598 scopus 로고    scopus 로고
    • Phase i safety, pharmacokinetic and pharmacodynamic studies of 2-methoxyestradiol alone or in combination with docetaxel in patients with locally recurrent or metastatic breast cancer
    • J. James, D.J. Murry, A.M. Treston, A.M. Storniolo, G.W. Sledge, and C. Sidor et al. Phase I safety, pharmacokinetic and pharmacodynamic studies of 2-methoxyestradiol alone or in combination with docetaxel in patients with locally recurrent or metastatic breast cancer Invest New Drugs 25 2006 41 48
    • (2006) Invest New Drugs , vol.25 , pp. 41-48
    • James, J.1    Murry, D.J.2    Treston, A.M.3    Storniolo, A.M.4    Sledge, G.W.5    Sidor, C.6
  • 17
    • 34547204029 scopus 로고    scopus 로고
    • Characterization of in vitro and in vivo metabolic pathways of the investigational anticancer agent, 2-methoxyestradiol
    • DOI 10.1002/jps.20837
    • N.J. Lakhani, A. Sparreboom, X. Xu, T.D. Veenstra, J. Venitz, and W.L. Dahut et al. Characterization of in vitro and in vivo metabolic pathways of the investigational anticancer agent, 2-methoxyestradiol J Pharm Sci 96 2007 1821 1831 (Pubitemid 47122958)
    • (2007) Journal of Pharmaceutical Sciences , vol.96 , Issue.7 , pp. 1821-1831
    • Lakhani, N.J.1    Sparreboom, A.2    Xu, X.3    Veenstra, T.D.4    Venitz, J.5    Dahut, W.L.6    Figg, W.D.7
  • 19
    • 84855188922 scopus 로고    scopus 로고
    • Synthesis, biological evaluation and molecular modeling of 1,2,3-triazole analogs of combretastatin A-1
    • O.W. Akselsen, K. Odlo, J.J. Cheng, G. Maccari, M. Botta, and T.V. Hansen Synthesis, biological evaluation and molecular modeling of 1,2,3-triazole analogs of combretastatin A-1 Bioorg Med Chem 20 2012 234 242
    • (2012) Bioorg Med Chem , vol.20 , pp. 234-242
    • Akselsen, O.W.1    Odlo, K.2    Cheng, J.J.3    Maccari, G.4    Botta, M.5    Hansen, T.V.6
  • 21
    • 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
    • DOI 10.1016/j.bmc.2008.03.049, PII S0968089608002745
    • K. Odlo, J. Hentzen, J. Fournier dit Chabert, S. Ducki, O.A.B.S.M. Gani, and I. Sylte et al. 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 16 2008 4829 4838 (Pubitemid 351625899)
    • (2008) Bioorganic and Medicinal Chemistry , vol.16 , Issue.9 , pp. 4829-4838
    • Odlo, K.1    Hentzen, J.2    Fournier Dit Chabert, J.3    Ducki, S.4    Gani, O.A.B.S.M.5    Sylte, I.6    Skrede, M.7    Florenes, V.A.8    Hansen, T.V.9
  • 22
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • DOI 10.1002/1521-3773(20020715)41:14<2596: :AID-ANIE2596>3.0.CO;2-4
    • V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless A stepwise Hüisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes Angew Chem Int Ed 41 2002 2596 2599 (Pubitemid 34803480)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.14 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 23
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • DOI 10.1021/jo011148j
    • C.W. Tornøe, C. Christensen, and M. Meldal Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J Org Chem 67 2002 3057 3064 (Pubitemid 34457265)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.9 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3
  • 24
    • 39549111477 scopus 로고    scopus 로고
    • Click chemistry reactions in medicinal chemistry: Applications of the 1,3-dipolar cycloaddition between azides and alkynes
    • DOI 10.1002/med.20107
    • G.C. Tron, T. Pirali, R.A. Billington, P.L. Canonico, G. Sorba, and A.A. Genazzani Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes Med Res Rev 28 2008 278 308 (Pubitemid 351281190)
    • (2008) Medicinal Research Reviews , vol.28 , Issue.2 , pp. 278-308
    • Tron, G.C.1    Pirali, T.2    Billington, R.A.3    Canonico, P.L.4    Sorba, G.5    Genazzani, A.A.6
  • 25
    • 34547272503 scopus 로고    scopus 로고
    • The growing applications of click chemistry
    • J.E. Moses, and A.D. Moorhouse The growing applications of click chemistry Chem Soc Rev 36 2007 1249 1262
    • (2007) Chem Soc Rev , vol.36 , pp. 1249-1262
    • Moses, J.E.1    Moorhouse, A.D.2
  • 26
    • 0023945929 scopus 로고
    • A rapid and simple MTT-based spectrophotometric assay for determining drug sensitivity in monolayer cultures
    • J.M. Edmondson, L.S. Armstrong, and A.O. Martinez A rapid and simple MTT-based spectrophotometric assay for determining drug sensitivity in monolayer cultures J Tissue Cult Meth 11 1988 15 17
    • (1988) J Tissue Cult Meth , vol.11 , pp. 15-17
    • Edmondson, J.M.1    Armstrong, L.S.2    Martinez, A.O.3
  • 29
    • 29644432244 scopus 로고
    • Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives
    • E.J. Corey, and B.B. Snider Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives J Am Chem Soc 94 1972 6190 6192
    • (1972) J Am Chem Soc , vol.94 , pp. 6190-6192
    • Corey, E.J.1    Snider, B.B.2
  • 30
    • 70350755331 scopus 로고    scopus 로고
    • The role of microtubules in cell biology
    • T. Fojo, Humana Press Totowa
    • M.A. Jordan, and L. Wilson The role of microtubules in cell biology T. Fojo, Neurobiology, and oncology 2008 Humana Press Totowa 47 81
    • (2008) Neurobiology, and Oncology , pp. 47-81
    • Jordan, M.A.1    Wilson, L.2
  • 31
    • 34248159068 scopus 로고    scopus 로고
    • Small molecule vascular disrupting agents: Potential new drugs for cancer treatment
    • S.X. Cai Small molecule vascular disrupting agents: potential new drugs for cancer treatment Recent Patents Anticancer Drug Discov 2 2007 79 101 (Pubitemid 46723154)
    • (2007) Recent Patents on Anti-Cancer Drug Discovery , vol.2 , Issue.1 , pp. 79-101
    • Cai, S.X.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.