메뉴 건너뛰기




Volumn 58, Issue 6, 2015, Pages 2623-2648

Design and synthesis of norendoxifen analogues with dual aromatase inhibitory and estrogen receptor modulatory activities

Author keywords

[No Author keywords available]

Indexed keywords

(4 (2 BROMOETHOXY)PHENYL)(4 NITROPHENYL)METHANONE; (4 HYDROXYPHENYL)(4 NITROPHENYL)METHANONE; (4 METHOXYPHENYL)(4 NITROPHENYL)METHANONE; 2 (4 (1,2 DIPHENYLBUT 1 EN 1 YL)PHENOXY)ACETAMIDE; 2 (4 (1,2 DIPHENYLBUT 1 EN 1 YL)PHENOXY)ETHAN 1 AMINE; 2 (4 (2 (4 FLUOROPHENYL) 1 (4 HYDROXYPHENYL)BUT 1 EN 1 YL)PHENOXY)ACETAMIDE; 2 (4 (2 ETHYL 1 (4 HYDROXYPHENYL)BUT 1 EN 1 YL)PHENOXY)ACETAMIDE; 4 (1 (4 (2 AMINO 2 OXOETHOXY)PHENYL) 1 (4 HYDROXYPHENYL)BUT 1 EN 2 YL)PHEYNYL PIVALATE; 4 (1 (4 (2 AMINOETHOXY)PHENYL) 1 (4 AMINOPHENYL)BUT 1EN 2 YL)PHENOL; 4 (1 (4 (2 AMINOETHOXY)PHENYL) 2 (4 FLUOROPHENYL)BUT 1EN 1 YL)PHENOL; 4 (1 (4 (2 AMINOETHOXY)PHENYL) 2 ETHYLBUT 1 EN 1 YL)PHENOL; 4 (1 (4 (2 AMINOETHOXY)PHENYL) 2 PHENYLBUT 1 EN 1 YL)ANILINE; 4 (1 (4 (2 BROMOETHOXY)PHENYL) 2 PHENYLBUT 1 EN 1 YL)ANILINE; 4 (1 (4 AMINOPHENYL) 1 (4 (2 BROMOETHOXY)PHENYL)BUT 1EN 2 YL)PHENYL PIVALATE; 4 (1,2 DIPHENYLBUT 1 EN 1 YL)PHENOL; 4' HYDROXYNORENDOXIFEN; 4,4' (1 (4 (2 AMINOETHOXY)PHENYL)BUT 1 ENE 1,2 DIYL) DIPHENOL; 4,4' (2 (4 FLUOROPHENYL)BUT 1 ENE 1,1 DIYL)DIPHENOL; 4,4' (2 ETHYLBUT 1 ENE 1,1 DIYL)DIPHENOL; 4,4' (2 PHENYLPENT 1 ENE 1,1 DIYL)DIPHENOL; 4,4' (2 PHENYLPROP 1 ENE 1,1 DIYL)DIPHENOL; 4,4' (2,2 DIPHENYLETHENE 1,1 DIYL)DIPHENOL; 4,4' (3 METHYL 2 PHENYLBUT 1 ENE 1,1 DIYL)DIPHENOL; ANTINEOPLASTIC AGENT; AROMATASE INHIBITOR; CYTOCHROME P450; NORENDOXIFEN DERIVATIVE; PYRROLIDINE DERIVATIVE; SELECTIVE ESTROGEN RECEPTOR MODULATOR; UNCLASSIFIED DRUG; UNINDEXED DRUG; AROMATASE; ESTROGEN RECEPTOR; N,N-DIDESMETHYL-4-HYDROXYTAMOXIFEN; TAMOXIFEN;

EID: 84925872644     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm501218e     Document Type: Article
Times cited : (36)

References (51)
  • 2
    • 0003964363 scopus 로고    scopus 로고
    • American Cancer Society, Inc. Atlanta, GA
    • Cancer Facts & Figures 2013; American Cancer Society, Inc.: Atlanta, GA, 2013.
    • (2013) Cancer Facts & Figures 2013
  • 3
    • 0000719778 scopus 로고    scopus 로고
    • Early Breast Cancer Trialists Collaborative, G. Tamoxifen for Early Breast Cancer: An Overview of the Randomised Trials
    • Clarke, M.; Collins, R.; Davies, C.; Godwin, J.; Gray, R.; Peto, R. Early Breast Cancer Trialists Collaborative, G. Tamoxifen for Early Breast Cancer: An Overview of the Randomised Trials Lancet 1998, 351, 1451-1467
    • (1998) Lancet , vol.351 , pp. 1451-1467
    • Clarke, M.1    Collins, R.2    Davies, C.3    Godwin, J.4    Gray, R.5    Peto, R.6
  • 5
    • 0036488531 scopus 로고    scopus 로고
    • Endocrine-Responsive Breast Cancer and Strategies for Combating Resistance
    • Ali, S.; Coombes, R. C. Endocrine-Responsive Breast Cancer and Strategies for Combating Resistance Nature Rev. Cancer 2002, 2, 101-112
    • (2002) Nature Rev. Cancer , vol.2 , pp. 101-112
    • Ali, S.1    Coombes, R.C.2
  • 6
    • 0030161996 scopus 로고    scopus 로고
    • Long Term Tamoxifen Therapy: Can an Antagonist Become an Agonist?
    • Santen, R. J. Long Term Tamoxifen Therapy: Can an Antagonist Become an Agonist? J. Clin. Endocrinol. Metab. 1996, 81, 2027-2029
    • (1996) J. Clin. Endocrinol. Metab. , vol.81 , pp. 2027-2029
    • Santen, R.J.1
  • 7
    • 0035498544 scopus 로고    scopus 로고
    • Anastrozole is Superior to Tamoxifen as First-Line Therapy in Hormone Receptor Positive Advanced Breast Carcinoma-Results of Two Randomized Trials Designed for Combined Analysis
    • Armidex Writing Committee on behalf of the Investigators Committee Members
    • Bonneterre, J.; Buzdar, A.; Nabholtz, J. M. A.; Robertson, J. F. R.; Thurlimann, B.; von Euler, M.; Sahmoud, T.; Webster, A.; Steinberg, M.; Armidex Writing Committee on behalf of the Investigators Committee Members Anastrozole is Superior to Tamoxifen as First-Line Therapy in Hormone Receptor Positive Advanced Breast Carcinoma-Results of Two Randomized Trials Designed for Combined Analysis Cancer 2001, 92, 2247-2258
    • (2001) Cancer , vol.92 , pp. 2247-2258
    • Bonneterre, J.1    Buzdar, A.2    Nabholtz, J.M.A.3    Robertson, J.F.R.4    Thurlimann, B.5    Von Euler, M.6    Sahmoud, T.7    Webster, A.8    Steinberg, M.9
  • 11
    • 37449028688 scopus 로고    scopus 로고
    • Effect of Anastrozole and Tamoxifen as Adjuvant Treatment for Early-Stage Breast Cancer: 100-Month Analysis of the ATAC Trial
    • Williams, N. Effect of Anastrozole and Tamoxifen as Adjuvant Treatment for Early-Stage Breast Cancer: 100-Month Analysis of the ATAC Trial Lancet Oncol. 2008, 9, 45-53
    • (2008) Lancet Oncol. , vol.9 , pp. 45-53
    • Williams, N.1
  • 12
    • 0036133521 scopus 로고    scopus 로고
    • Role of Low Levels of Endogenous Estrogen in Regulation of Bone Resorption in Late Postmenopausal Women
    • Heshmati, H. M.; Khosla, S.; Robins, S. P.; OFallon, W. M.; Melton, L. J.; Riggs, B. L. Role of Low Levels of Endogenous Estrogen in Regulation of Bone Resorption in Late Postmenopausal Women J. Bone Miner. Res. 2002, 17, 172-178
    • (2002) J. Bone Miner. Res. , vol.17 , pp. 172-178
    • Heshmati, H.M.1    Khosla, S.2    Robins, S.P.3    Ofallon, W.M.4    Melton, L.J.5    Riggs, B.L.6
  • 13
    • 65649119341 scopus 로고    scopus 로고
    • A Womans Heart. The Impact of Adjuvant Endocrine Therapy on Cardiovascular Health
    • Ewer, M. S.; Gluck, S. A Womans Heart. The Impact of Adjuvant Endocrine Therapy on Cardiovascular Health Cancer 2009, 115, 1813-1826
    • (2009) Cancer , vol.115 , pp. 1813-1826
    • Ewer, M.S.1    Gluck, S.2
  • 14
    • 40749087694 scopus 로고    scopus 로고
    • Cardiac Toxicity in Breast Cancer Survivors: Review of Potential Cardiac Problems
    • Bird, B. R. J. H.; Swain, S. M. Cardiac Toxicity in Breast Cancer Survivors: Review of Potential Cardiac Problems Clin. Cancer Res. 2008, 14, 14-24
    • (2008) Clin. Cancer Res. , vol.14 , pp. 14-24
    • Bird, B.R.J.H.1    Swain, S.M.2
  • 15
    • 24944494988 scopus 로고    scopus 로고
    • The Effects of Aromatase Inhibitors on Lipids and Thrombosis
    • Bundred, N. J. The Effects of Aromatase Inhibitors on Lipids and Thrombosis Br. J. Cancer 2005, 93, S23-S27
    • (2005) Br. J. Cancer , vol.93 , pp. 23-S27
    • Bundred, N.J.1
  • 16
    • 77957839142 scopus 로고    scopus 로고
    • Musculoskeletal Adverse Events Asociated with Adjuvant Aromatase Inhibitors
    • Khan, Q. J.; ODea, A. P.; Sharma, P. Musculoskeletal Adverse Events Asociated with Adjuvant Aromatase Inhibitors J. Oncol. 2010, 654348 10.1155/2010/654348
    • (2010) J. Oncol. , pp. 654348
    • Khan, Q.J.1    Odea, A.P.2    Sharma, P.3
  • 17
    • 20444448539 scopus 로고    scopus 로고
    • Additive Antitumor Effect of Aromatase Inhibitor Letrozole and Antiestrogen Fulvestrant in a Postmenopausal Breast Cancer Model
    • Jelovac, D.; Macedo, L.; Goloubeva, O. G.; Handratta, V.; Brodie, A. M. H. Additive Antitumor Effect of Aromatase Inhibitor Letrozole and Antiestrogen Fulvestrant in a Postmenopausal Breast Cancer Model Cancer Res. 2005, 65, 5439-5444
    • (2005) Cancer Res. , vol.65 , pp. 5439-5444
    • Jelovac, D.1    Macedo, L.2    Goloubeva, O.G.3    Handratta, V.4    Brodie, A.M.H.5
  • 18
    • 0037157603 scopus 로고    scopus 로고
    • Anastrozole Alone or in Combination with Tamoxifen Versus Tamoxifen Alone for Adjuvant Treatment of Postmenopausal Women with Early Breast Cancer: First Results of the ATAC Randomised Trial
    • Baum, M.; Buzdar, A. U.; Cuzick, J.; Forbes, J.; Houghton, J.; Klijn, J. G. M.; Sahmoud, T.; Grp, A. T. Anastrozole Alone or in Combination with Tamoxifen Versus Tamoxifen Alone for Adjuvant Treatment of Postmenopausal Women with Early Breast Cancer: First Results of the ATAC Randomised Trial Lancet 2002, 359, 2131-2139
    • (2002) Lancet , vol.359 , pp. 2131-2139
    • Baum, M.1    Buzdar, A.U.2    Cuzick, J.3    Forbes, J.4    Houghton, J.5    Klijn, J.G.M.6    Sahmoud, T.7    Grp, A.T.8
  • 19
    • 84860321539 scopus 로고    scopus 로고
    • The Tamoxifen Metabolite Norendoxifen is a Potent and Selective Inhibitor of Aromatase (CYP19) and a Potential Lead Compound for Novel Therapeutic Agents
    • Lu, W. J.; Xu, C.; Pei, Z. F.; Mayhoub, A. S.; Cushman, M.; Flockhart, D. A. The Tamoxifen Metabolite Norendoxifen Is a Potent and Selective Inhibitor of Aromatase (CYP19) and a Potential Lead Compound for Novel Therapeutic Agents Breast Cancer Res. Treat. 2012, 133, 99-109
    • (2012) Breast Cancer Res. Treat. , vol.133 , pp. 99-109
    • Lu, W.J.1    Xu, C.2    Pei, Z.F.3    Mayhoub, A.S.4    Cushman, M.5    Flockhart, D.A.6
  • 20
    • 84879058938 scopus 로고    scopus 로고
    • Synthesis of Mixed (E, Z)-, (E)-, and (Z)-Norendoxifen with Dual Aromatase Inhibitory and Estrogen Receptor Modulatory Activities
    • Lv, W.; Liu, J.; Lu, D.; Flockhart, D. A.; Cushman, M. Synthesis of Mixed (E, Z)-, (E)-, and (Z)-Norendoxifen with Dual Aromatase Inhibitory and Estrogen Receptor Modulatory Activities J. Med. Chem. 2013, 56, 4611-4618
    • (2013) J. Med. Chem. , vol.56 , pp. 4611-4618
    • Lv, W.1    Liu, J.2    Lu, D.3    Flockhart, D.A.4    Cushman, M.5
  • 22
    • 0032446607 scopus 로고    scopus 로고
    • The Structural Basis of Estrogen Receptor/Coactivator Recognition and the Antagonism of This Interaction by Tamoxifen
    • Shiau, A. K.; Barstad, D.; Loria, P. M.; Cheng, L.; Kushner, P. J.; Agard, D. A.; Greene, G. L. The Structural Basis of Estrogen Receptor/Coactivator Recognition and the Antagonism of This Interaction by Tamoxifen Cell 1998, 95, 927-937
    • (1998) Cell , vol.95 , pp. 927-937
    • Shiau, A.K.1    Barstad, D.2    Loria, P.M.3    Cheng, L.4    Kushner, P.J.5    Agard, D.A.6    Greene, G.L.7
  • 25
    • 84856234626 scopus 로고    scopus 로고
    • Tamoxifen Metabolites as Active Inhibitors of Aromatase in the Treatment of Breast Cancer
    • Lu, W. J.; Desta, Z.; Flockhart, D. A. Tamoxifen Metabolites as Active Inhibitors of Aromatase in the Treatment of Breast Cancer Breast Cancer Res. Treat. 2012, 131, 473-481
    • (2012) Breast Cancer Res. Treat. , vol.131 , pp. 473-481
    • Lu, W.J.1    Desta, Z.2    Flockhart, D.A.3
  • 26
    • 0034704637 scopus 로고    scopus 로고
    • Stereoselectivity of Methyl Aryldiazoacetate Cyclopropanations of 1,1-Diarylethylene. Asymmetric Aynthesis of a Cyclopropyl Analogue of Tamoxifen
    • Davies, H. M. L.; Nagashima, T.; Klino, J. L. Stereoselectivity of Methyl Aryldiazoacetate Cyclopropanations of 1,1-Diarylethylene. Asymmetric Aynthesis of a Cyclopropyl Analogue of Tamoxifen Org. Lett. 2000, 2, 823-826
    • (2000) Org. Lett. , vol.2 , pp. 823-826
    • Davies, H.M.L.1    Nagashima, T.2    Klino, J.L.3
  • 27
    • 0030908101 scopus 로고    scopus 로고
    • Synthesis of a Versatile Purification Handle for Use with Boc Chemistry Solid Phase Peptide Synthesis
    • Canne, L. E.; Winston, R. L.; Kent, S. B. H. Synthesis of a Versatile Purification Handle for Use with Boc Chemistry Solid Phase Peptide Synthesis Tetrahedron Lett. 1997, 38, 3361-3364
    • (1997) Tetrahedron Lett. , vol.38 , pp. 3361-3364
    • Canne, L.E.1    Winston, R.L.2    Kent, S.B.H.3
  • 28
    • 0030459216 scopus 로고    scopus 로고
    • Estrogenic Triarylethylene Acetic Acids: Effect of Structural Variation on Estrogen Receptor Affinity and Estrogenic Potency and Efficacy in MCF-7 Cells
    • Ruenitz, P. C.; Bourne, C. S.; Sullivan, K. J.; Moore, S. A. Estrogenic Triarylethylene Acetic Acids: Effect of Structural Variation on Estrogen Receptor Affinity and Estrogenic Potency and Efficacy in MCF-7 Cells J. Med. Chem. 1996, 39, 4853-4859
    • (1996) J. Med. Chem. , vol.39 , pp. 4853-4859
    • Ruenitz, P.C.1    Bourne, C.S.2    Sullivan, K.J.3    Moore, S.A.4
  • 29
    • 84925869194 scopus 로고    scopus 로고
    • Hydroxynorendoxifen, an Active Tamoxifen Metabolite, Possesses Dual Aromatase Inhibitory and Estrogen Receptor Modulatory Activities
    • Liu, J.; Lu, D.; Lu, J.; Lv, W.; Cushman, M.; Desta, Z.; Flockhart, D. A. Hydroxynorendoxifen, an Active Tamoxifen Metabolite, Possesses Dual Aromatase Inhibitory and Estrogen Receptor Modulatory Activities Clin. Pharmacol. Ther. 2014, 95, S21-S21
    • (2014) Clin. Pharmacol. Ther. , vol.95 , pp. 21-S21
    • Liu, J.1    Lu, D.2    Lu, J.3    Lv, W.4    Cushman, M.5    Desta, Z.6    Flockhart, D.A.7
  • 31
    • 0029893855 scopus 로고    scopus 로고
    • New Highly Stereoselective Synthesis of (Z)-4-Hydroxytamoxifen and (Z)-4-Hydroxytoremifene via McMurry Reaction
    • Gauthier, S.; Mailhot, J.; Labrie, F. New Highly Stereoselective Synthesis of (Z)-4-Hydroxytamoxifen and (Z)-4-Hydroxytoremifene via McMurry Reaction J. Org. Chem. 1996, 61, 3890-3893
    • (1996) J. Org. Chem. , vol.61 , pp. 3890-3893
    • Gauthier, S.1    Mailhot, J.2    Labrie, F.3
  • 33
    • 0037435046 scopus 로고    scopus 로고
    • Antiestrogens and Selective Estrogen Receptor Modulators as Multifunctional Medicines. 1. Receptor Interactions
    • Jordan, V. C. Antiestrogens and Selective Estrogen Receptor Modulators as Multifunctional Medicines. 1. Receptor Interactions J. Med. Chem. 2003, 46, 883-908
    • (2003) J. Med. Chem. , vol.46 , pp. 883-908
    • Jordan, V.C.1
  • 34
    • 0021735339 scopus 로고
    • Structural Requirements for the Pharmacological Activity of Nonsteroidal Antiestrogens in Vitro
    • Jordan, V. C.; Lieberman, M. E.; Cormier, E.; Koch, R.; Bagley, J. R.; Ruenitz, P. C. Structural Requirements for the Pharmacological Activity of Nonsteroidal Antiestrogens In Vitro Mol. Pharmacol. 1984, 26, 272-278
    • (1984) Mol. Pharmacol. , vol.26 , pp. 272-278
    • Jordan, V.C.1    Lieberman, M.E.2    Cormier, E.3    Koch, R.4    Bagley, J.R.5    Ruenitz, P.C.6
  • 35
    • 2642593030 scopus 로고    scopus 로고
    • The Key to the Antiestrogenic Mechanism of Raloxifene is Amino Acid 351 (Aspartate) in the Estrogen Receptor
    • Levenson, A. S.; Jordan, V. C. The Key to the Antiestrogenic Mechanism of Raloxifene Is Amino Acid 351 (Aspartate) in the Estrogen Receptor Cancer Res. 1998, 58, 1872-1875
    • (1998) Cancer Res. , vol.58 , pp. 1872-1875
    • Levenson, A.S.1    Jordan, V.C.2
  • 36
    • 0034665358 scopus 로고    scopus 로고
    • Allosteric Silencing of Activating Function 1 in the 4-Hydroxytamoxifen Estrogen Receptor Complex is Induced by Substituting Glycine for Aspartate at Amino Acid 351
    • Schafer, J. M.; Liu, H.; Bentrem, D. J.; Zapf, J. W.; Jordan, V. C. Allosteric Silencing of Activating Function 1 in the 4-Hydroxytamoxifen Estrogen Receptor Complex Is Induced by Substituting Glycine for Aspartate at Amino Acid 351 Cancer Res. 2000, 60, 5097-5105
    • (2000) Cancer Res. , vol.60 , pp. 5097-5105
    • Schafer, J.M.1    Liu, H.2    Bentrem, D.J.3    Zapf, J.W.4    Jordan, V.C.5
  • 37
    • 17644387537 scopus 로고    scopus 로고
    • Endoxifen (4-Hydroxy- N -desmethyl-tamoxifen) Has Anti-estrogenic Effects in Breast Cancer Cells with Potency Similar to 4-Hydroxy-tamoxifen
    • Lim, Y. C.; Desta, Z.; Flockhart, D. A.; Skaar, T. C. Endoxifen (4-Hydroxy- N -desmethyl-tamoxifen) Has Anti-estrogenic Effects in Breast Cancer Cells with Potency Similar to 4-Hydroxy-tamoxifen Cancer Chemother. Pharmacol. 2005, 55, 471-478
    • (2005) Cancer Chemother. Pharmacol. , vol.55 , pp. 471-478
    • Lim, Y.C.1    Desta, Z.2    Flockhart, D.A.3    Skaar, T.C.4
  • 38
    • 0009201860 scopus 로고
    • 1,1-Bis(p -hydroxyphenyl)-2,2-diethylethylene, a New Isomer of Stilbestrol
    • Miquel, J. F. 1,1-Bis(p -hydroxyphenyl)-2,2-diethylethylene, a New Isomer of Stilbestrol Acta Chem. Scand. 1958, 12, 274-280
    • (1958) Acta Chem. Scand. , vol.12 , pp. 274-280
    • Miquel, J.F.1
  • 39
    • 35348816924 scopus 로고    scopus 로고
    • An Expeditious Synthesis of Tamoxifen, a Representative SERM (Selective Estrogen Receptor Modulator), via the Three-Component Coupling Reaction among Aromatic Aldehyde, Cinnamyltrimethylsilane, and β-Chlorophenetole
    • Shiina, I.; Sano, Y.; Nakata, K.; Suzuki, M.; Yokoyama, T.; Sasaki, A.; Orikasa, T.; Miyamoto, T.; Ikekita, M.; Nagahara, Y.; Hasome, Y. An Expeditious Synthesis of Tamoxifen, a Representative SERM (Selective Estrogen Receptor Modulator), via the Three-Component Coupling Reaction Among Aromatic Aldehyde, Cinnamyltrimethylsilane, and β-Chlorophenetole Bioorg. Med. Chem. 2007, 15, 7599-7617
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 7599-7617
    • Shiina, I.1    Sano, Y.2    Nakata, K.3    Suzuki, M.4    Yokoyama, T.5    Sasaki, A.6    Orikasa, T.7    Miyamoto, T.8    Ikekita, M.9    Nagahara, Y.10    Hasome, Y.11
  • 40
    • 0027368698 scopus 로고
    • Reaction of Pyrylium Salts with Nucleophiles. 23: Triarylethene Derivatives Containing an Oxyalkyleneamino or Oxyalkylene- N- pyridinium Side Chain
    • Stanciuc, O.; Balaban, A. T. Reaction of Pyrylium Salts with Nucleophiles. 23: Triarylethene Derivatives Containing an Oxyalkyleneamino or Oxyalkylene- N- pyridinium Side Chain J. Pharm. Sci. 1993, 82, 927-933
    • (1993) J. Pharm. Sci. , vol.82 , pp. 927-933
    • Stanciuc, O.1    Balaban, A.T.2
  • 41
    • 84858025727 scopus 로고    scopus 로고
    • Radiosynthesis and Evaluation of an F-18-Labeled Positron Emission Tomography (PET) Radioligand for Brain Histamine Subtype-3 Receptors Based on a Nonimidazole 2-Aminoethylbenzofuran Chemotype
    • Bao, X. F.; Lu, S. Y.; Liow, J. S.; Zoghbi, S. S.; Jenko, K. J.; Clark, D. T.; Gladding, R. L.; Innis, R. B.; Pike, V. W. Radiosynthesis and Evaluation of an F-18-Labeled Positron Emission Tomography (PET) Radioligand for Brain Histamine Subtype-3 Receptors Based on a Nonimidazole 2-Aminoethylbenzofuran Chemotype J. Med. Chem. 2012, 55, 2406-2415
    • (2012) J. Med. Chem. , vol.55 , pp. 2406-2415
    • Bao, X.F.1    Lu, S.Y.2    Liow, J.S.3    Zoghbi, S.S.4    Jenko, K.J.5    Clark, D.T.6    Gladding, R.L.7    Innis, R.B.8    Pike, V.W.9
  • 42
    • 0037153283 scopus 로고    scopus 로고
    • Investigations on Estrogen Receptor Binding. The Estrogenic, Antiestrogenic, and Cytotoxic Properties of C2-Alkyl-Substituted 1,1-Bis(4-hydroxyphenyl)-2-phenylethenes
    • Lubczyk, V.; Bachmann, H.; Gust, R. Investigations on Estrogen Receptor Binding. The Estrogenic, Antiestrogenic, and Cytotoxic Properties of C2-Alkyl-Substituted 1,1-Bis(4-hydroxyphenyl)-2-phenylethenes J. Med. Chem. 2002, 45, 5358-5364
    • (2002) J. Med. Chem. , vol.45 , pp. 5358-5364
    • Lubczyk, V.1    Bachmann, H.2    Gust, R.3
  • 44
    • 33845949018 scopus 로고    scopus 로고
    • Insights into the General and Efficient Cross McMurry Reactions between Ketones
    • Duan, X. F.; Zeng, J.; Lu, J. W.; Zhang, Z. B. Insights into the General and Efficient Cross McMurry Reactions between Ketones J. Org. Chem. 2006, 71, 9873-9876
    • (2006) J. Org. Chem. , vol.71 , pp. 9873-9876
    • Duan, X.F.1    Zeng, J.2    Lu, J.W.3    Zhang, Z.B.4
  • 45
    • 0019830645 scopus 로고
    • Preparation of Tritium-Labeled 4-Hydroxy-α-[ p -(2-(N -pyrrolidinyl)ethoxy)phenyl]-α′-nitrostilbene (CN-928), a Biologically Important Metabolite of the Antiestrogen CI-628
    • Katzenellenbogen, J. A.; Tatee, T.; Robertson, D. W. Preparation of Tritium-Labeled 4-Hydroxy-α-[ p -(2-(N -pyrrolidinyl)ethoxy)phenyl]-α′-nitrostilbene (CN-928), a Biologically Important Metabolite of the Antiestrogen CI-628 J. Labelled Compd. Radiopharm. 1981, 18, 865-879
    • (1981) J. Labelled Compd. Radiopharm. , vol.18 , pp. 865-879
    • Katzenellenbogen, J.A.1    Tatee, T.2    Robertson, D.W.3
  • 46
    • 0034067895 scopus 로고    scopus 로고
    • Triarylethylene Bisphenols with a Novel Cycle Are Ligands for the Estrogen Receptor
    • Kim, S. H.; Katzenellenbogen, J. A. Triarylethylene Bisphenols with a Novel Cycle Are Ligands for the Estrogen Receptor Bioorg. Med. Chem. 2000, 8, 785-793
    • (2000) Bioorg. Med. Chem. , vol.8 , pp. 785-793
    • Kim, S.H.1    Katzenellenbogen, J.A.2
  • 47
    • 1242273824 scopus 로고    scopus 로고
    • Design, Synthesis, and Biological Evaluation of Doxorubicin-Formaldehyde Conjugates Targeted to Breast Cancer Cells
    • Burke, P. J.; Koch, T. H. Design, Synthesis, and Biological Evaluation of Doxorubicin-Formaldehyde Conjugates Targeted to Breast Cancer Cells J. Med. Chem. 2004, 47, 1193-1206
    • (2004) J. Med. Chem. , vol.47 , pp. 1193-1206
    • Burke, P.J.1    Koch, T.H.2
  • 48
    • 77950028099 scopus 로고    scopus 로고
    • Endoxifen is a New Potent Inhibitor of PKC: A Potential Therapeutic Agent for Bipolar Disorder
    • Ali, S. M.; Ahmad, A.; Shahabuddin, S.; Ahmad, M. U.; Sheikh, S.; Ahmad, I. Endoxifen is a New Potent Inhibitor of PKC: A Potential Therapeutic Agent for Bipolar Disorder Bioorg. Med. Chem. Lett. 2010, 20, 2665-2667
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 2665-2667
    • Ali, S.M.1    Ahmad, A.2    Shahabuddin, S.3    Ahmad, M.U.4    Sheikh, S.5    Ahmad, I.6
  • 49
    • 20344405467 scopus 로고    scopus 로고
    • Palladium-Catalyzed Coupling of Thiol Esters with Aryl and Primary and Secondary Alkyl Organoindium Reagents
    • Fausett, B. W.; Liebeskind, L. S. Palladium-Catalyzed Coupling of Thiol Esters with Aryl and Primary and Secondary Alkyl Organoindium Reagents J. Org. Chem. 2005, 70, 4851-4853
    • (2005) J. Org. Chem. , vol.70 , pp. 4851-4853
    • Fausett, B.W.1    Liebeskind, L.S.2
  • 50
    • 34247633521 scopus 로고    scopus 로고
    • BF3-H2O catalyzed Fries Rearrangement of Phenolic Esters
    • Prakash, G. K. S.; Panja, C.; Mathew, T.; Olah, G. A. BF3-H2O catalyzed Fries Rearrangement of Phenolic Esters Catal. Lett. 2007, 114, 24-29
    • (2007) Catal. Lett. , vol.114 , pp. 24-29
    • Prakash, G.K.S.1    Panja, C.2    Mathew, T.3    Olah, G.A.4
  • 51
    • 80053928122 scopus 로고    scopus 로고
    • Enantiomers of Naringenin as Pleiotropic, Stereoselective Inhibitors of Cytochrome P450 Isoforms
    • Lu, W. J.; Ferlito, V.; Xu, C.; Flockhart, D. A.; Caccamese, S. Enantiomers of Naringenin as Pleiotropic, Stereoselective Inhibitors of Cytochrome P450 Isoforms Chirality 2011, 23, 891-896
    • (2011) Chirality , vol.23 , pp. 891-896
    • Lu, W.J.1    Ferlito, V.2    Xu, C.3    Flockhart, D.A.4    Caccamese, S.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.