메뉴 건너뛰기




Volumn 96, Issue 1, 2005, Pages 51-58

Structure-activity relationships of 2-, 4-, or 6-substituted estrogens as aromatase inhibitors

Author keywords

2 Halogeno estrogens; 6 Alkyl estrogens; 6 Aryl estrogens; Aromatase inhibition; Competitive inhibitor; Structure activity relationship

Indexed keywords

6ALPHA BENZYL 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6ALPHA BENZYLESTRONE; 6ALPHA BUTOXY 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6ALPHA BUTOXYESTRONE; 6ALPHA BUTYL 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6ALPHA BUTYLESTRONE; 6ALPHA ETHOXY 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6ALPHA ETHOXYESTRONE; 6ALPHA METHOXY 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6ALPHA METHOXYESTRONE; 6ALPHA METHYL 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6ALPHA METHYLESTRONE; 6ALPHA PHENYL 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6ALPHA PHENYLESTRONE; 6BETA BENZYL 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6BETA BENZYLESTRONE; 6BETA BUTOXY 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6BETA BUTYL 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6BETA BUTYLESTRONE; 6BETA ETHOXY 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6BETA METHOXY 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6BETA METHYL 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6BETA METHYLESTRONE; 6BETA PHENPROPYL 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6BETA PHENPROPYLESTRONE; 6BETA PHENYL 3 HYDROXYESTRA 1,3,5(10) TRIEN 17 ONE; 6BETA PHENYLESTRONE; AROMATASE INHIBITOR; ESTROGEN DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 23144448160     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2005.01.028     Document Type: Article
Times cited : (36)

References (43)
  • 1
    • 0016272566 scopus 로고
    • The involvement of human placental microsomal cytochrome P-450 in aromatization
    • E.A. Thompson Jr., and P.K. Siiteri The involvement of human placental microsomal cytochrome P-450 in aromatization J. Biol. Chem. 249 1974 5373 5378
    • (1974) J. Biol. Chem. , vol.249 , pp. 5373-5378
    • Thompson Jr., E.A.1    Siiteri, P.K.2
  • 2
    • 0023180688 scopus 로고
    • Purification and characterization of human placental aromatase cytochrome P-450
    • J.T. Kellis Jr., and L.E. Vickery Purification and characterization of human placental aromatase cytochrome P-450 J. Biol. Chem. 262 1987 4413 4420
    • (1987) J. Biol. Chem. , vol.262 , pp. 4413-4420
    • Kellis Jr., J.T.1    Vickery, L.E.2
  • 3
    • 0025872595 scopus 로고
    • Purification of human placental aromatase cytochrome P-450 with monoclonal antibody and its characterization
    • N. Yoshida, and Y. Osawa Purification of human placental aromatase cytochrome P-450 with monoclonal antibody and its characterization Biochemistry 30 1991 3003 3010
    • (1991) Biochemistry , vol.30 , pp. 3003-3010
    • Yoshida, N.1    Osawa, Y.2
  • 4
    • 0001828104 scopus 로고
    • Aromatase inhibitors: Specific inhibitors of oestrogen biosynthesis
    • D. Berg M. Plemel Ellis Horwood Ltd. Chichester
    • D.F. Covey Aromatase inhibitors: specific inhibitors of oestrogen biosynthesis D. Berg M. Plemel Steroid Biosynthesis Inhibitors: Pharmaceutical and Agrochemical Aspects 1988 Ellis Horwood Ltd. Chichester 534 571
    • (1988) Steroid Biosynthesis Inhibitors: Pharmaceutical and Agrochemical Aspects , pp. 534-571
    • Covey, D.F.1
  • 5
    • 0027273894 scopus 로고
    • Mechanism of human placental aromatase: A new active site model
    • S.S. Oh, and C.H. Robinson Mechanism of human placental aromatase: a new active site model J. Steroid Biochem. Mol. Biol. 44 1993 389 397
    • (1993) J. Steroid Biochem. Mol. Biol. , vol.44 , pp. 389-397
    • Oh, S.S.1    Robinson, C.H.2
  • 7
    • 0027295265 scopus 로고
    • Competitive product inhibition of aromatase by natural estrogens
    • Y. Shimizu, C. Yarborough, and Y. Osawa Competitive product inhibition of aromatase by natural estrogens J. Steroid Biochem. Mol. Biol. 44 1993 651 656
    • (1993) J. Steroid Biochem. Mol. Biol. , vol.44 , pp. 651-656
    • Shimizu, Y.1    Yarborough, C.2    Osawa, Y.3
  • 8
    • 0027314085 scopus 로고
    • Multiple functions of aromatase and the active site structure; Aromatase is the placental estrogen 2-hydroxylase
    • Y. Osawa, T. Higashiyama, Y. Shimizu, and C. Yarhorough Multiple functions of aromatase and the active site structure; aromatase is the placental estrogen 2-hydroxylase J. Steroid Biochem. Mol. Biol. 44 1993 469 480
    • (1993) J. Steroid Biochem. Mol. Biol. , vol.44 , pp. 469-480
    • Osawa, Y.1    Higashiyama, T.2    Shimizu, Y.3    Yarhorough, C.4
  • 11
    • 0024793429 scopus 로고
    • Recent developments in aromatase inhibitors on a potential treatment of estrogen-dependent breast cancer
    • G.P. Ellis G.B. West Elsevier Science Publishers B.V. Amsterdam
    • L. Banting, P.J. Nicholls, M.A. Shaw, and H.J. Smith Recent developments in aromatase inhibitors on a potential treatment of estrogen-dependent breast cancer G.P. Ellis G.B. West Progress in Medicinal Chemistry vol. 26 1989 Elsevier Science Publishers B.V. Amsterdam 253 298
    • (1989) Progress in Medicinal Chemistry , vol.26 , pp. 253-298
    • Banting, L.1    Nicholls, P.J.2    Shaw, M.A.3    Smith, H.J.4
  • 13
    • 0242457702 scopus 로고    scopus 로고
    • The intratumoral aromatase model: Studies with aromatase inhibitors and anti estrogens
    • A.M.H. Brodie, D. Jelovac, and B. Long The intratumoral aromatase model: studies with aromatase inhibitors and anti estrogens J. Steroid Biochem. Mol. Biol. 86 2003 283 288
    • (2003) J. Steroid Biochem. Mol. Biol. , vol.86 , pp. 283-288
    • Brodie, A.M.H.1    Jelovac, D.2    Long, B.3
  • 15
    • 0017132777 scopus 로고
    • Studies on the mechanism of estrogen biosynthesis in rat ovary
    • A.M.H. Brodie, W.C. Schwarzel, and H.J. Brodie Studies on the mechanism of estrogen biosynthesis in rat ovary J. Steroid Biochem. 7 1976 787 793
    • (1976) J. Steroid Biochem. , vol.7 , pp. 787-793
    • Brodie, A.M.H.1    Schwarzel, W.C.2    Brodie, H.J.3
  • 16
    • 0000106947 scopus 로고
    • Substrate-induced inactivation of aromatase by allenic and acetylenic steroids
    • B.M. Metcalf, C.L. Wright, J.P. Burkhart, and J.O. Johnston Substrate-induced inactivation of aromatase by allenic and acetylenic steroids J. Am. Chem. Soc. 103 1981 3221 3222
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 3221-3222
    • Metcalf, B.M.1    Wright, C.L.2    Burkhart, J.P.3    Johnston, J.O.4
  • 17
    • 0024817037 scopus 로고
    • Aromatase inhibitions and experimental antitumor activity of FCE 24304, MDL 18962, and SH 489
    • E. Di Salle, G. Briatico, D. Giudici, G. Ornati, and T. Zaccheo Aromatase inhibitions and experimental antitumor activity of FCE 24304, MDL 18962, and SH 489 J. Steroid Biochem. 34 1989 431 434
    • (1989) J. Steroid Biochem. , vol.34 , pp. 431-434
    • Di Salle, E.1    Briatico, G.2    Giudici, D.3    Ornati, G.4    Zaccheo, T.5
  • 18
    • 0022550064 scopus 로고
    • 1-Methyl-1,4-androstadiene-3,17-dione (SH 489): Characterization of an irreversible inhibitor of estrogen biosynthesis
    • D. Henderson, G. Norbisrath, and U. Kerb 1-Methyl-1,4-androstadiene-3,17- dione (SH 489): characterization of an irreversible inhibitor of estrogen biosynthesis J. Steroid Biochem. 24 1987 303 306
    • (1987) J. Steroid Biochem. , vol.24 , pp. 303-306
    • Henderson, D.1    Norbisrath, G.2    Kerb, U.3
  • 19
    • 0036006421 scopus 로고    scopus 로고
    • Synthesis of 2,16α- and 4,16α-difluoroestradiols and their 11β-methoxy derivatives as potential estrogen receptor-binding radiopharmaceuticals
    • Y. Seimbille, H. Ali, and J.E. van Lier Synthesis of 2,16α- and 4,16α-difluoroestradiols and their 11β-methoxy derivatives as potential estrogen receptor-binding radiopharmaceuticals J. Chem. Soc. Perkin Trans. 1 2002 657 663
    • (2002) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 657-663
    • Seimbille, Y.1    Ali, H.2    Van Lier, J.E.3
  • 20
    • 37049089993 scopus 로고
    • Reaction of benzeneseleneyl halides with estrogens
    • H. Ali, and J.E. van Lier Reaction of benzeneseleneyl halides with estrogens J. Chem. Soc. Perkin Trans. 1 1991 269 271
    • (1991) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 269-271
    • Ali, H.1    Van Lier, J.E.2
  • 21
    • 0006977267 scopus 로고
    • N-Bromosuccinimide-dimethylformide: A mild selective nuclear monobromination reagent for reactive aromatic compounds
    • R.H. Mitchell, Y.H. Lai, and R.V. Williams N-Bromosuccinimide- dimethylformide: a mild selective nuclear monobromination reagent for reactive aromatic compounds J. Org. Chem. 44 1979 4733 4735
    • (1979) J. Org. Chem. , vol.44 , pp. 4733-4735
    • Mitchell, R.H.1    Lai, Y.H.2    Williams, R.V.3
  • 22
    • 0029008622 scopus 로고
    • Synthesis antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methylestradiol, and endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site
    • M. Cushman, H.M. He, J.A. Katzenellenbogen, C.M. Lin, and E. Hanel Synthesis antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methylestradiol, and endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site J. Med. Chem. 38 1995 2041 2049
    • (1995) J. Med. Chem. , vol.38 , pp. 2041-2049
    • Cushman, M.1    He, H.M.2    Katzenellenbogen, J.A.3    Lin, C.M.4    Hanel, E.5
  • 23
    • 33544473519 scopus 로고
    • Synthesis of 2-methoxy- and 4-methoxyestrogens with halogen-methoxy exchange reactions
    • M. Numazawa, Y. Ogura, K. Kimura, and M. Nagaoka Synthesis of 2-methoxy- and 4-methoxyestrogens with halogen-methoxy exchange reactions J. Chem. Res. Syn. 11 1985 348 349
    • (1985) J. Chem. Res. Syn. , vol.11 , pp. 348-349
    • Numazawa, M.1    Ogura, Y.2    Kimura, K.3    Nagaoka, M.4
  • 24
    • 0017093511 scopus 로고
    • Convenient large scale preparation of catechol estrogens
    • G. Stubenrauch, and R. Knuppen Convenient large scale preparation of catechol estrogens Steroids 28 1976 733 741
    • (1976) Steroids , vol.28 , pp. 733-741
    • Stubenrauch, G.1    Knuppen, R.2
  • 25
    • 0028286267 scopus 로고
    • 6-Alkyl- and 6-aryl-androst-4-ene-3,17-diones as aromatase inhibitors, synthesis and structure-activity relationships
    • M. Numazawa, and M. Oshibe 6-Alkyl- and 6-aryl-androst-4-ene-3,17-diones as aromatase inhibitors, synthesis and structure-activity relationships J. Med. Chem. 37 1994 1312 1319
    • (1994) J. Med. Chem. , vol.37 , pp. 1312-1319
    • Numazawa, M.1    Oshibe, M.2
  • 26
    • 0031727843 scopus 로고    scopus 로고
    • 6-Phenylaliphatic-substituted androst-4-ene-3,17-diones as aromatase
    • M. Numazawa, and S. Yamaguchi 6-Phenylaliphatic-substituted androst-4-ene-3,17-diones as aromatase J. Steroid Biochem. Mol. Biol. 67 1998 41 48
    • (1998) J. Steroid Biochem. Mol. Biol. , vol.67 , pp. 41-48
    • Numazawa, M.1    Yamaguchi, S.2
  • 27
    • 0033758790 scopus 로고    scopus 로고
    • Probing the binding pocket of the active site of aromatase with 6-ether or 6-ester substituted androst-4-ene-3,17-diones and their diene and triene analogs
    • M. Numazawa, M. Shelangouski, and M. Nagaoka Probing the binding pocket of the active site of aromatase with 6-ether or 6-ester substituted androst-4-ene-3,17-diones and their diene and triene analogs Steroids 65 2000 871 882
    • (2000) Steroids , vol.65 , pp. 871-882
    • Numazawa, M.1    Shelangouski, M.2    Nagaoka, M.3
  • 28
    • 0142216815 scopus 로고
    • Biological aromatization of steroids
    • K.J. Ryan Biological aromatization of steroids J. Biol. Chem. 234 1959 268 272
    • (1959) J. Biol. Chem. , vol.234 , pp. 268-272
    • Ryan, K.J.1
  • 30
    • 0041616545 scopus 로고    scopus 로고
    • Erithacus Software Limited, Surrey, UK
    • Grafit Version 5.0.3, Erithacus Software Limited, Surrey, UK, 2001.
    • (2001) Grafit Version 5.0.3
  • 31
    • 0029131311 scopus 로고
    • Further studies on 6-alkylandrost-4-ene-3,17-diones as aromatase inhibitors: Elongation of the 6-alkyl chain
    • M. Numazawa, and M. Oshibe Further studies on 6-alkylandrost-4-ene-3,17- diones as aromatase inhibitors: elongation of the 6-alkyl chain Steroids 60 1995 506 511
    • (1995) Steroids , vol.60 , pp. 506-511
    • Numazawa, M.1    Oshibe, M.2
  • 32
    • 0024504548 scopus 로고
    • Effect of steroid D-ring modification on suicide inactivation and competitive inhibition of aromatase by analogues of androst-1,4-diene-3,17-dione
    • P.F. Sherwin, P.C. McMullan, and D.F. Covey Effect of steroid D-ring modification on suicide inactivation and competitive inhibition of aromatase by analogues of androst-1,4-diene-3,17-dione J. Med. Chem. 32 1989 651 658
    • (1989) J. Med. Chem. , vol.32 , pp. 651-658
    • Sherwin, P.F.1    McMullan, P.C.2    Covey, D.F.3
  • 33
    • 0029899588 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of 6-substituted androst-4-ene analogs as aromatase inhibitors
    • M. Numazawa, T. Kamiyama, M. Tachibana, and M. Oshibe Synthesis and structure-activity relationships of 6-substituted androst-4-ene analogs as aromatase inhibitors J. Med. Chem. 39 1996 2245 2252
    • (1996) J. Med. Chem. , vol.39 , pp. 2245-2252
    • Numazawa, M.1    Kamiyama, T.2    Tachibana, M.3    Oshibe, M.4
  • 34
    • 0021271612 scopus 로고
    • Inhibition of human estrogen synthase (aromatase) by flavones
    • J.T. Kellis Jr., and L.E. Vickery Inhibition of human estrogen synthase (aromatase) by flavones Science 225 1984 1032 1034
    • (1984) Science , vol.225 , pp. 1032-1034
    • Kellis Jr., J.T.1    Vickery, L.E.2
  • 36
    • 0031915796 scopus 로고    scopus 로고
    • Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens. a site-directed mutagenesis study
    • Y.C. Kao, C. Zhou, M. Sherman, C.A. Laughton, and S. Chen Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens. A site-directed mutagenesis study Environ. Health. Perspect. 106 1998 85 92
    • (1998) Environ. Health. Perspect. , vol.106 , pp. 85-92
    • Kao, Y.C.1    Zhou, C.2    Sherman, M.3    Laughton, C.A.4    Chen, S.5
  • 38
    • 3242794236 scopus 로고    scopus 로고
    • Synthesis and aromatase inhibitory activity of novel pyridine-containing isoflavones
    • Y.-W. Kim, J.C. Hackett, and R.W. Brueggemeier Synthesis and aromatase inhibitory activity of novel pyridine-containing isoflavones J. Med. Chem. 47 2004 4032 4040
    • (2004) J. Med. Chem. , vol.47 , pp. 4032-4040
    • Kim, Y.-W.1    Hackett, J.C.2    Brueggemeier, R.W.3
  • 39
    • 0030298217 scopus 로고    scopus 로고
    • Crystal structure, receptor bindings, and gene regulation of 2- and 4-nitroestradiols
    • E. Palomino, M.J. Heeg, M.J. Pilat, M. Hafner, L. Polin, and S.C. Brooks Crystal structure, receptor bindings, and gene regulation of 2- and 4-nitroestradiols Steroids 61 1996 670 676
    • (1996) Steroids , vol.61 , pp. 670-676
    • Palomino, E.1    Heeg, M.J.2    Pilat, M.J.3    Hafner, M.4    Polin, L.5    Brooks, S.C.6
  • 40
    • 37049084805 scopus 로고
    • Synthesis and receptor binding affinity of 7α- and 17α-substituted 2- and 4-chloroestradiol derivatives
    • H. Ali, and J.E. van Lier Synthesis and receptor binding affinity of 7α- and 17α-substituted 2- and 4-chloroestradiol derivatives J. Chem. Soc. Perkin Trans. 1 1991 2485 2491
    • (1991) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 2485-2491
    • Ali, H.1    Van Lier, J.E.2
  • 41
    • 0030660115 scopus 로고    scopus 로고
    • Inhibition of the estrogen specific mitogenic response of MCF-7 cells by selected analogs of estradiol: A 3D QSAR study
    • T.E. Wiese, L.A. Polin, E. Palomino, and S.C. Brooks Inhibition of the estrogen specific mitogenic response of MCF-7 cells by selected analogs of estradiol: a 3D QSAR study J. Med. Chem. 40 1997 3659 3669
    • (1997) J. Med. Chem. , vol.40 , pp. 3659-3669
    • Wiese, T.E.1    Polin, L.A.2    Palomino, E.3    Brooks, S.C.4
  • 42
    • 0025895161 scopus 로고
    • Methyl and bromo derivatives of estradiol are agonistic ligands for the estrogen receptor of MCF-7 breast cancer cells
    • G. Vollmer, W. Wünsche, N. Schütze, B. Feit, and R. Knuppen Methyl and bromo derivatives of estradiol are agonistic ligands for the estrogen receptor of MCF-7 breast cancer cells J. Steroid Biochem. Mol. Biol. 39 1991 359 366
    • (1991) J. Steroid Biochem. Mol. Biol. , vol.39 , pp. 359-366
    • Vollmer, G.1    Wünsche, W.2    Schütze, N.3    Feit, B.4    Knuppen, R.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.