메뉴 건너뛰기




Volumn 53, Issue 15, 2010, Pages 5749-5758

Replacement of imidazolyl by pyridyl in biphenylmethylenes results in selective CYP17 and dual CYP17/CYP11B1 inhibitors for the treatment of prostate cancer

Author keywords

[No Author keywords available]

Indexed keywords

4' (PYRIDIN 4 YLMETHYL)BIPHENYL 3,4 DIOL; ABIRATERONE; ALDOSTERONE SYNTHASE; AROMATASE; BIPHENYL DERIVATIVE; BIPHENYLMETHYLENE DERIVATIVE; CYTOCHROME P450 11B1; CYTOCHROME P450 17; CYTOCHROME P450 3A4; CYTOCHROME P450 INHIBITOR; CYTOCHROME P450 ISOENZYME; KETOCONAZOLE; METYRAPONE; UNCLASSIFIED DRUG;

EID: 77955388983     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100317b     Document Type: Article
Times cited : (55)

References (52)
  • 1
    • 0027529115 scopus 로고
    • Basis for hormonal management of advanced prostate cancer
    • Geller, J. Basis for hormonal management of advanced prostate cancer Cancer 1993, 71, 1039-1045
    • (1993) Cancer , vol.71 , pp. 1039-1045
    • Geller, J.1
  • 2
    • 0023775543 scopus 로고
    • Histological and functional changes of the testis tissue during GnRH agonist treatment of prostatic cancer
    • Huhtaniemi, I.; Nikula, H.; Parvinen, M.; Rannikko, S. Histological and functional changes of the testis tissue during GnRH agonist treatment of prostatic cancer Am. J. Clin. Oncol. 1988, 11 (Suppl. 1) S11-S15
    • (1988) Am. J. Clin. Oncol. , vol.11 , Issue.SUPPL. 1
    • Huhtaniemi, I.1    Nikula, H.2    Parvinen, M.3    Rannikko, S.4
  • 4
    • 0037226103 scopus 로고    scopus 로고
    • Novel mutations of androgen receptor: A possible mechanism of bicalutamide withdrawal syndrome
    • Hara, T.; Miyazaki, J.; Araki, H.; Yamaoka, M.; Kanzaki, N.; Kusaka, M.; Miyamoto, M. Novel mutations of androgen receptor: A possible mechanism of bicalutamide withdrawal syndrome Cancer Res. 2003, 63, 149-153
    • (2003) Cancer Res. , vol.63 , pp. 149-153
    • Hara, T.1    Miyazaki, J.2    Araki, H.3    Yamaoka, M.4    Kanzaki, N.5    Kusaka, M.6    Miyamoto, M.7
  • 5
    • 0034125195 scopus 로고    scopus 로고
    • Glucocorticoids can promote androgen-independent growth of prostate cancer cells through a mutated androgen receptor
    • Zhao, X. Y.; Malloy, P. J.; Krishnan, A. V.; Swami, S.; Navone, N. M.; Peehl, D. M.; Feldman, D. Glucocorticoids can promote androgen-independent growth of prostate cancer cells through a mutated androgen receptor Nat. Med. 2000, 6, 703-706
    • (2000) Nat. Med. , vol.6 , pp. 703-706
    • Zhao, X.Y.1    Malloy, P.J.2    Krishnan, A.V.3    Swami, S.4    Navone, N.M.5    Peehl, D.M.6    Feldman, D.7
  • 6
    • 0012293592 scopus 로고
    • Cytochrome P450c17(steroid 17?-hydroxylase/C17,20-lyase): Cloning of human adrenal and testis cDNA indicates the same gene is expressed in both tissues
    • Chung, B. C.; Picardo-Leonard, J.; Hanui, M.; Bienkowski, M.; Hall, P. F.; Shively, J. E.; Miller, W. L. Cytochrome P450c17(steroid 17?-hydroxylase/C17,20-lyase): cloning of human adrenal and testis cDNA indicates the same gene is expressed in both tissues Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 407-411
    • (1987) Proc. Natl. Acad. Sci. U.S.A. , vol.84 , pp. 407-411
    • Chung, B.C.1    Picardo-Leonard, J.2    Hanui, M.3    Bienkowski, M.4    Hall, P.F.5    Shively, J.E.6    Miller, W.L.7
  • 7
    • 67649710142 scopus 로고    scopus 로고
    • The utility of 5-alpha reductase inhibitors in the prevention and diagnosis of prostate cancer
    • Reed, A. B.; Parekh, D. J. The utility of 5-alpha reductase inhibitors in the prevention and diagnosis of prostate cancer Curr. Opin. Urol. 2009, 19, 238-242
    • (2009) Curr. Opin. Urol. , vol.19 , pp. 238-242
    • Reed, A.B.1    Parekh, D.J.2
  • 8
    • 0036132203 scopus 로고    scopus 로고
    • 5-Phenyl substituted 1-methyl-2-pyridones and 4?-substituted biphenyl-4-carboxylic acids: Synthesis and evaluation as inhibitors of steroid-5?-reductase type 1 and 2
    • Picard, F.; Schulz, T.; Hartmann, R. W. 5-Phenyl substituted 1-methyl-2-pyridones and 4?-substituted biphenyl-4-carboxylic acids: synthesis and evaluation as inhibitors of steroid-5?-reductase type 1 and 2 Bioorg. Med. Chem. 2002, 10, 437-448
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 437-448
    • Picard, F.1    Schulz, T.2    Hartmann, R.W.3
  • 9
    • 0033738449 scopus 로고    scopus 로고
    • 6-Substituted 1 H -quinolin-2-ones and 2-methoxy-quinolines: Synthesis and evaluation as inhibitors of steroid 5? reductases types 1 and 2
    • Baston, E.; Palusczak, A.; Hartmann, R. W. 6-Substituted 1 H -quinolin-2-ones and 2-methoxy-quinolines: synthesis and evaluation as inhibitors of steroid 5? reductases types 1 and 2 Eur. J. Med. Chem. 2000, 35, 931-940
    • (2000) Eur. J. Med. Chem. , vol.35 , pp. 931-940
    • Baston, E.1    Palusczak, A.2    Hartmann, R.W.3
  • 10
    • 33846479832 scopus 로고    scopus 로고
    • Unusual and underappreciated: Small cell carcinoma of the prostate
    • Palmgren, J. S.; Karavadia, S. S.; Wakefield, M. R. Unusual and underappreciated: small cell carcinoma of the prostate Semin. Oncol. 2007, 34, 22-29
    • (2007) Semin. Oncol. , vol.34 , pp. 22-29
    • Palmgren, J.S.1    Karavadia, S.S.2    Wakefield, M.R.3
  • 12
    • 34248657567 scopus 로고    scopus 로고
    • Cushing syndrome associated with prostatic tumor adrenocorticotropic hormone (ACTH) expression after maximal androgen blockade therapy
    • Kataoka, K.; Akasaka, Y.; Nakajima, K.; Nagao, K.; Hara, H.; Miura1, K.; Ishii, N. Cushing syndrome associated with prostatic tumor adrenocorticotropic hormone (ACTH) expression after maximal androgen blockade therapy Int. J. Urol. 2007, 14, 436-439
    • (2007) Int. J. Urol. , vol.14 , pp. 436-439
    • Kataoka, K.1    Akasaka, Y.2    Nakajima, K.3    Nagao, K.4    Hara, H.5    Miura, K.6    Ishii, N.7
  • 13
    • 0036737855 scopus 로고    scopus 로고
    • Ectopic adrenocorticotropic hormone syndrome caused by metastatic carcinoma of the prostate: Therapeutic response to ketoconazole
    • Hussein, W. I.; Kowalyk, S.; Hoogwerf, B. J. Ectopic adrenocorticotropic hormone syndrome caused by metastatic carcinoma of the prostate: therapeutic response to ketoconazole Endocr. Pract. 2002, 8, 381-384
    • (2002) Endocr. Pract. , vol.8 , pp. 381-384
    • Hussein, W.I.1    Kowalyk, S.2    Hoogwerf, B.J.3
  • 14
    • 0023790912 scopus 로고
    • Rat prostatic weight regression in reaction to ketoconazole, cyproterone acetate, and RU 23908 as adjuncts to a depot formulation of gonadotropin- releasing hormone analog
    • Lamberts, S. W. J.; Uitterlinden, P.; De Jong, F. H. Rat prostatic weight regression in reaction to ketoconazole, cyproterone acetate, and RU 23908 as adjuncts to a depot formulation of gonadotropin-releasing hormone analog Cancer Res. 1988, 48, 6063-6068
    • (1988) Cancer Res. , vol.48 , pp. 6063-6068
    • Lamberts, S.W.J.1    Uitterlinden, P.2    De Jong, F.H.3
  • 18
    • 20944449560 scopus 로고    scopus 로고
    • Novel C-17-heteroaryl steroidal CYP17 inhibitors/antiandrogens: Synthesis, in vitro biological activity, pharmacokinetics, and antitumor activity in the LAPC4 human prostate cancer xenograft model
    • Handratta, V. D.; Vasaitis, T. S.; Njar, V. C. O.; Gediya, L. K.; Kataria, R.; Chopra, P.; Newman, D., Jr.; Farquhar, R.; Guo, Z.; Qiu, Y.; Brodie, A. M. H. Novel C-17-heteroaryl steroidal CYP17 inhibitors/antiandrogens: synthesis, in vitro biological activity, pharmacokinetics, and antitumor activity in the LAPC4 human prostate cancer xenograft model J. Med. Chem. 2005, 48, 2972-2984
    • (2005) J. Med. Chem. , vol.48 , pp. 2972-2984
    • Handratta, V.D.1    Vasaitis, T.S.2    Njar, V.C.O.3    Gediya, L.K.4    Kataria, R.5    Chopra, P.6    Newman Jr., D.7    Farquhar, R.8    Guo, Z.9    Qiu, Y.10    Brodie, A.M.H.11
  • 21
    • 0030059847 scopus 로고    scopus 로고
    • Tetrahydronaphthalenes: Influence of heterocyclic substituents on inhibition of steroidogenic enzymes P450 arom and P450 17
    • Wächter, G. A.; Hartmann, R. W.; Sergejew, T.; Grün, G. L.; Ledergerber, D. Tetrahydronaphthalenes: Influence of heterocyclic substituents on inhibition of steroidogenic enzymes P450 arom and P450 17 J. Med. Chem. 1996, 39, 834-841
    • (1996) J. Med. Chem. , vol.39 , pp. 834-841
    • Wächter, G.A.1    Hartmann, R.W.2    Sergejew, T.3    Grün, G.L.4    Ledergerber, D.5
  • 22
    • 0029763048 scopus 로고    scopus 로고
    • 3- and 4-pyridylalkyl adamantanecarboxylates: Inhibitors of human cytochrome P450 17? (17?-hydroxylase/C17,20-lyase). Potential nonsteroidal agents for the treatment of prostatic cancer
    • Chan, F. C. Y.; Potter, G. A.; Barrie, S. E.; Haynes, B. P.; Rowlands, M. G.; Houghton, J.; Jarman, M. 3- and 4-pyridylalkyl adamantanecarboxylates: inhibitors of human cytochrome P450 17? (17?-hydroxylase/C17,20-lyase). Potential nonsteroidal agents for the treatment of prostatic cancer J. Med. Chem. 1996, 39, 3319-3323
    • (1996) J. Med. Chem. , vol.39 , pp. 3319-3323
    • Chan, F.C.Y.1    Potter, G.A.2    Barrie, S.E.3    Haynes, B.P.4    Rowlands, M.G.5    Houghton, J.6    Jarman, M.7
  • 23
    • 0032835607 scopus 로고    scopus 로고
    • Imidazole substituted biphenyls: A new class of highly potent and in vivo active inhibitors of P450 17 as potential therapeutics for treatment of prostate cancer
    • Wachall, B. G.; Hector, M.; Zhuang, Y.; Hartmann, R. W. Imidazole substituted biphenyls: A new class of highly potent and in vivo active inhibitors of P450 17 as potential therapeutics for treatment of prostate cancer Bioorg. Med. Chem. 1999, 7, 1913-1924
    • (1999) Bioorg. Med. Chem. , vol.7 , pp. 1913-1924
    • Wachall, B.G.1    Hector, M.2    Zhuang, Y.3    Hartmann, R.W.4
  • 24
    • 0043016030 scopus 로고    scopus 로고
    • N -(4-Biphenylmethyl)imidazoles as potential therapeutics for the treatment of prostate cancer: Metabolic robustness due to fluorine substitution?
    • Leroux, F.; Hutschenreuter, T. U.; Charriere, C.; Scopelliti, R.; Hartmann, R. W. N -(4-Biphenylmethyl)imidazoles as potential therapeutics for the treatment of prostate cancer: metabolic robustness due to fluorine substitution? Helv. Chim. Acta 2003, 86, 2671-2686
    • (2003) Helv. Chim. Acta , vol.86 , pp. 2671-2686
    • Leroux, F.1    Hutschenreuter, T.U.2    Charriere, C.3    Scopelliti, R.4    Hartmann, R.W.5
  • 25
    • 1242352932 scopus 로고    scopus 로고
    • Synthesis of hydroxy derivatives of highly potent non-steroidal CYP 17 Inhibitors as potential metabolites and evaluation of their activity by a non cellular assay using recombinant human enzyme
    • Hutschenreuter, T. U.; Ehmer, P. E.; Hartmann, R. W. Synthesis of hydroxy derivatives of highly potent non-steroidal CYP 17 Inhibitors as potential metabolites and evaluation of their activity by a non cellular assay using recombinant human enzyme J. Enzyme Inhib. Med. Chem. 2004, 19, 17-32
    • (2004) J. Enzyme Inhib. Med. Chem. , vol.19 , pp. 17-32
    • Hutschenreuter, T.U.1    Ehmer, P.E.2    Hartmann, R.W.3
  • 27
    • 49149091871 scopus 로고    scopus 로고
    • Synthesis, biological evaluation, and molecular modeling studies of methylene imidazole substituted biaryls as inhibitors of human 17-hydroxylase-17,20-lyase (CYP17). Part II: Core rigidification and influence of substituents at the methylene bridge
    • Hu, Q.; Negri, M.; Jahn-Hoffmann, K.; Zhuang, Y.; Olgen, S.; Bartels, M.; Müller-Vieira, U.; Lauterbach, T.; Hartmann, R. W. Synthesis, biological evaluation, and molecular modeling studies of methylene imidazole substituted biaryls as inhibitors of human 17-hydroxylase-17,20-lyase (CYP17). Part II: Core rigidification and influence of substituents at the methylene bridge Bioorg. Med. Chem. 2008, 16, 7715-7727
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 7715-7727
    • Hu, Q.1    Negri, M.2    Jahn-Hoffmann, K.3    Zhuang, Y.4    Olgen, S.5    Bartels, M.6    Müller-Vieira, U.7    Lauterbach, T.8    Hartmann, R.W.9
  • 28
    • 67349083573 scopus 로고    scopus 로고
    • Novel CYP17 inhibitors: Synthesis, biological evaluation, structure?activity relationships and modeling of methoxy- and hydroxy-substituted methyleneimidazolyl biphenyls
    • Hille, U. E.; Hu, Q.; Vock, C.; Negri, M.; Bartels, M.; Müller-Vieira, U.; Lauterbach, T.; Hartmann, R. W. Novel CYP17 inhibitors: synthesis, biological evaluation, structure?activity relationships and modeling of methoxy- and hydroxy-substituted methyleneimidazolyl biphenyls Eur. J. Med. Chem. 2009, 44, 2765-2775
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 2765-2775
    • Hille, U.E.1    Hu, Q.2    Vock, C.3    Negri, M.4    Bartels, M.5    Müller-Vieira, U.6    Lauterbach, T.7    Hartmann, R.W.8
  • 29
    • 77953104461 scopus 로고    scopus 로고
    • The role of fluorine substitution in biphenyl methylene imidazole type CYP17 inhibitors for the treatment of prostate carcinoma
    • Hu, Q.; Negri, M.; Olgen, S.; Hartmann, R. W. The role of fluorine substitution in biphenyl methylene imidazole type CYP17 inhibitors for the treatment of prostate carcinoma ChemMedChem 2010, 5, 899-910
    • (2010) ChemMedChem , vol.5 , pp. 899-910
    • Hu, Q.1    Negri, M.2    Olgen, S.3    Hartmann, R.W.4
  • 30
    • 77954326488 scopus 로고    scopus 로고
    • Isopropylidene substitution increases activity and selectivity of biphenyl methylene 4-pyridine type CYP17 inhibitors
    • Hu, Q.; Yin, L.; Jagusch, C.; Hille, U. E.; Hartmann, R. W. Isopropylidene substitution increases activity and selectivity of biphenyl methylene 4-pyridine type CYP17 inhibitors J. Med. Chem. 2010, 53, 5049-5053
    • (2010) J. Med. Chem. , vol.53 , pp. 5049-5053
    • Hu, Q.1    Yin, L.2    Jagusch, C.3    Hille, U.E.4    Hartmann, R.W.5
  • 31
    • 71849117108 scopus 로고    scopus 로고
    • Steroidogenic cytochrome P450 (CYP) enzymes as drug targets: Combining substructures of known CYP inhibitors leads to compounds with different inhibitory profile
    • Hille, U. E.; Hu, Q.; Pinto-Bazurco Mendieta, M. A. E.; Bartels, M.; Vock, C. A.; Lauterbach, T.; Hartmann, R. W. Steroidogenic cytochrome P450 (CYP) enzymes as drug targets: Combining substructures of known CYP inhibitors leads to compounds with different inhibitory profile C. R. Chim. 2009, 12, 1117-1126
    • (2009) C. R. Chim. , vol.12 , pp. 1117-1126
    • Hille, U.E.1    Hu, Q.2    Pinto-Bazurco Mendieta, M.A.E.3    Bartels, M.4    Vock, C.A.5    Lauterbach, T.6    Hartmann, R.W.7
  • 32
    • 0028305222 scopus 로고
    • Aromatase inhibitors. Syntheses and structure?activity studies of novel pyridyl-substituted indanones, indans, and tetralins
    • Hartmann, R. W.; Bayer, H.; Grün, G. Aromatase inhibitors. Syntheses and structure?activity studies of novel pyridyl-substituted indanones, indans, and tetralins J. Med. Chem. 1994, 37, 1275-1281
    • (1994) J. Med. Chem. , vol.37 , pp. 1275-1281
    • Hartmann, R.W.1    Bayer, H.2    Grün, G.3
  • 35
    • 33746712854 scopus 로고    scopus 로고
    • Lead optimization providing a series of flavone derivatives as potent nonsteroidal inhibitors of the cytochrome P450 aromatase enzyme
    • Gobbi, S.; Cavalli, A.; Rampa, A.; Belluti, F.; Piazzi, L.; Paluszcak, A.; Hartmann, R. W.; Recanatini, M.; Bisi, A. Lead optimization providing a series of flavone derivatives as potent nonsteroidal inhibitors of the cytochrome P450 aromatase enzyme J. Med. Chem. 2006, 49, 4777-4780
    • (2006) J. Med. Chem. , vol.49 , pp. 4777-4780
    • Gobbi, S.1    Cavalli, A.2    Rampa, A.3    Belluti, F.4    Piazzi, L.5    Paluszcak, A.6    Hartmann, R.W.7    Recanatini, M.8    Bisi, A.9
  • 36
    • 58149087304 scopus 로고    scopus 로고
    • In vivo active aldosterone synthase inhibitors with improved selectivity: Lead optimization providing a series of pyridine substituted 3,4-dihydro-1 H -quinolin-2-one derivatives
    • Lucas, S.; Heim, R.; Ries, C.; Schewe, K. E.; Birk, B.; Hartmann, R. W. In vivo active aldosterone synthase inhibitors with improved selectivity: lead optimization providing a series of pyridine substituted 3,4-dihydro-1 H -quinolin-2-one derivatives J. Med. Chem. 2008, 51, 8077-8087
    • (2008) J. Med. Chem. , vol.51 , pp. 8077-8087
    • Lucas, S.1    Heim, R.2    Ries, C.3    Schewe, K.E.4    Birk, B.5    Hartmann, R.W.6
  • 37
    • 53549099432 scopus 로고    scopus 로고
    • Novel aldosterone synthase inhibitors with extended carbocyclic skeleton by a combined ligand-based and structure-based drug design approach
    • Lucas, S.; Heim, R.; Negri, M.; Antes, I.; Ries, C.; Schewe, K. E.; Bisi, A.; Gobbi, S.; Hartmann, R. W. Novel aldosterone synthase inhibitors with extended carbocyclic skeleton by a combined ligand-based and structure-based drug design approach J. Med. Chem. 2008, 51, 6138-6149
    • (2008) J. Med. Chem. , vol.51 , pp. 6138-6149
    • Lucas, S.1    Heim, R.2    Negri, M.3    Antes, I.4    Ries, C.5    Schewe, K.E.6    Bisi, A.7    Gobbi, S.8    Hartmann, R.W.9
  • 38
    • 14944355617 scopus 로고    scopus 로고
    • Synthesis and evaluation of (pyridylmethylene)tetrahydronaphthalenes/- indanes and structurally modified derivatives: Potent and selective inhibitors of aldosterone synthase
    • DOI 10.1021/jm0492397
    • Ulmschneider, S.; Müller-Vieira, U.; Klein, C. D.; Antes, I.; Lengauer, T.; Hartmann, R. W. Synthesis and evaluation of (pyridylmethylene) tetrahydronaphthalenes/-indanes and structurally modified derivatives: potent and selective inhibitors of aldosterone synthase J. Med. Chem. 2005, 48, 1563-1575 (Pubitemid 40364563)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.5 , pp. 1563-1575
    • Ulmschneider, S.1    Muller-Vieira, U.2    Klein, C.D.3    Antes, I.4    Lengauer, T.5    Hartmann, R.W.6
  • 40
    • 0014722772 scopus 로고
    • Inhibitors of adrenal steroid biosynthesis
    • Temple, T. E.; Liddle, G. W. Inhibitors of adrenal steroid biosynthesis Annu. Rev. pharmacol. 1970, 10, 199-218
    • (1970) Annu. Rev. pharmacol. , vol.10 , pp. 199-218
    • Temple, T.E.1    Liddle, G.W.2
  • 41
    • 0034484809 scopus 로고    scopus 로고
    • Development of a simple and rapid assay for the evaluation of inhibitors of human 17alpha-hydroxylase-C(17,20)-lyase (P450cl7) by coexpression of P450cl7 with NADPH-cytochrome-P450-reductase in Escherichia coli
    • Ehmer, P. B.; Jose, J.; Hartmann, R. W. Development of a simple and rapid assay for the evaluation of inhibitors of human 17alpha-hydroxylase-C(17,20)- lyase (P450cl7) by coexpression of P450cl7 with NADPH-cytochrome-P450-reductase in Escherichia coli J. Steroid Biochem. Mol. Biol. 2000, 75, 57-63
    • (2000) J. Steroid Biochem. Mol. Biol. , vol.75 , pp. 57-63
    • Ehmer, P.B.1    Jose, J.2    Hartmann, R.W.3
  • 42
    • 0029016986 scopus 로고
    • Cloning of CYP11B1 and CYP11B2 from normal human adrenal and their functional expression in COS-7 and V79 chinese hamster cells
    • Denner, K.; Doehmer, J.; Bernhardt, R. Cloning of CYP11B1 and CYP11B2 from normal human adrenal and their functional expression in COS-7 and V79 chinese hamster cells Endocr. Res. 1995, 21, 443-448
    • (1995) Endocr. Res. , vol.21 , pp. 443-448
    • Denner, K.1    Doehmer, J.2    Bernhardt, R.3
  • 43
    • 0036345081 scopus 로고    scopus 로고
    • Development of a test system for inhibitors of human aldosterone synthase (CYP11B2): Screening in fission yeast and evaluation of selectivity in V79 cells
    • Ehmer, P. B.; Bureik, M.; Bernhardt, R.; Müller, U.; Hartmann, R. W. Development of a test system for inhibitors of human aldosterone synthase (CYP11B2): screening in fission yeast and evaluation of selectivity in V79 cells J. Steroid Biochem. Mol. Biol. 2002, 81, 173-179
    • (2002) J. Steroid Biochem. Mol. Biol. , vol.81 , pp. 173-179
    • Ehmer, P.B.1    Bureik, M.2    Bernhardt, R.3    Müller, U.4    Hartmann, R.W.5
  • 44
    • 0022470925 scopus 로고
    • Aromatase inhibitors. Synthesis and evaluation of mammary tumor inhibiting activity of 3-alkylated 3-(4-aminophenyl)piperidine-2,6-diones
    • Hartmann, R. W.; Batzl, C. Aromatase inhibitors. Synthesis and evaluation of mammary tumor inhibiting activity of 3-alkylated 3-(4-aminophenyl) piperidine-2,6-diones J. Med. Chem. 1986, 29, 1362-1369
    • (1986) J. Med. Chem. , vol.29 , pp. 1362-1369
    • Hartmann, R.W.1    Batzl, C.2
  • 45
    • 0028167769 scopus 로고
    • Disorders of steroid 11β-hydroxylase isozymes
    • White, P. C.; Curnow, K. M.; Pascoe, L. Disorders of steroid 11β-hydroxylase isozymes Endocr. Rev. 1994, 15, 421-38
    • (1994) Endocr. Rev. , vol.15 , pp. 421-38
    • White, P.C.1    Curnow, K.M.2    Pascoe, L.3
  • 46
    • 70349208754 scopus 로고    scopus 로고
    • Estrogens as regulators of bone health in men
    • Vandenput, L.; Ohlsson, C. Estrogens as regulators of bone health in men Nat. Rev. Endocrinol. 2009, 5, 437-43
    • (2009) Nat. Rev. Endocrinol. , vol.5 , pp. 437-43
    • Vandenput, L.1    Ohlsson, C.2
  • 47
    • 67649659873 scopus 로고    scopus 로고
    • Estrogens, brain, and behavior: Lessons from knockout mouse models
    • Hill, R. A.; Boon, W. C. Estrogens, brain, and behavior: lessons from knockout mouse models Semin. Reprod. Med. 2009, 27, 218-228
    • (2009) Semin. Reprod. Med. , vol.27 , pp. 218-228
    • Hill, R.A.1    Boon, W.C.2
  • 49
    • 27144449695 scopus 로고    scopus 로고
    • Designed multiple ligands. An emerging drug discovery paradigm
    • Richard, M.; Zoran, R. Designed multiple ligands. An emerging drug discovery paradigm J. Med. Chem. 2005, 48, 6523-6543
    • (2005) J. Med. Chem. , vol.48 , pp. 6523-6543
    • Richard, M.1    Zoran, R.2
  • 51
    • 70449389897 scopus 로고    scopus 로고
    • Polysulfated/sulfonated compounds for the development of drugs at the crossroad of viral infection and oncogenesis
    • Marco, R.; Chiara, U. Polysulfated/sulfonated compounds for the development of drugs at the crossroad of viral infection and oncogenesis Curr. Pharm. Des. 2009, 15, 2946-2957
    • (2009) Curr. Pharm. Des. , vol.15 , pp. 2946-2957
    • Marco, R.1    Chiara, U.2
  • 52
    • 77649204688 scopus 로고    scopus 로고
    • Selectively nonselective kinase inhibition: Striking the right balance
    • Richard, M. Selectively nonselective kinase inhibition: striking the right balance J. Med. Chem. 2010, 53, 1413-1437
    • (2010) J. Med. Chem. , vol.53 , pp. 1413-1437
    • Richard, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.