메뉴 건너뛰기




Volumn 40, Issue 7, 1997, Pages 1112-1129

19-Nor-10-azasteroids: A novel class of inhibitors for human steroid 5α-reductases 1 and 2

Author keywords

[No Author keywords available]

Indexed keywords

17BETA (N TERT BUTYLCARBAMOYL) 19 NOR 10 AZA 4 ANDROSTEN 3 ONE; FINASTERIDE; STEROID 5ALPHA REDUCTASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 2642697958     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960807v     Document Type: Article
Times cited : (70)

References (80)
  • 1
    • 0028173882 scopus 로고
    • Steroid 5α-Reductases: Two Genes/Two Enzymes
    • (a) Russell, D. W.; Wilson, J. D. Steroid 5α-Reductases: Two Genes/Two Enzymes. Annu. Rev. Biochem. 1994, 63, 25-61.
    • (1994) Annu. Rev. Biochem. , vol.63 , pp. 25-61
    • Russell, D.W.1    Wilson, J.D.2
  • 3
    • 0000144674 scopus 로고
    • Chemical Control of Androgen Action
    • Rasmusson, G. H. Chemical Control of Androgen Action. Annu. Rep. Med. Chem. 1986, 22, 179-188.
    • (1986) Annu. Rep. Med. Chem. , vol.22 , pp. 179-188
    • Rasmusson, G.H.1
  • 4
    • 0025724954 scopus 로고
    • Benign Prostatic Hyperplasia: Pathogenesis and Medical Therapy
    • Geller, J. Benign Prostatic Hyperplasia: Pathogenesis and Medical Therapy. J Am. Geriatr. Soc. 1991, 39, 1208-1266.
    • (1991) J Am. Geriatr. Soc. , vol.39 , pp. 1208-1266
    • Geller, J.1
  • 5
    • 0025980402 scopus 로고
    • Role of 5α-Reductase Inhibitors in the Treatment of Advanced Prostatic Carcinoma
    • (a) Gormley, G. J. Role of 5α-Reductase Inhibitors in the Treatment of Advanced Prostatic Carcinoma. Urol. Clin. North Am. 1991, 18, 93-98.
    • (1991) Urol. Clin. North Am. , vol.18 , pp. 93-98
    • Gormley, G.J.1
  • 7
    • 0027994006 scopus 로고
    • The Effect of Finasteride, a 5α-Reductase Inhibitor, on Scalp Skin Testosterone and Dihydrotestosterone Concentrations in Patients with Male Pattern Baldness
    • Dallob, A. L.; Sadick, N. S.; Unger, W.; Lipert, S.; Geissler, L. A.; Gregoire, S. L.; Nguyen, H. H.; Moore, E. C.; Tanaka, W. K. The Effect of Finasteride, a 5α-Reductase Inhibitor, on Scalp Skin Testosterone and Dihydrotestosterone Concentrations in Patients with Male Pattern Baldness. J. Clin. Endocrinol. Metab. 1994, 79, 703-706.
    • (1994) J. Clin. Endocrinol. Metab. , vol.79 , pp. 703-706
    • Dallob, A.L.1    Sadick, N.S.2    Unger, W.3    Lipert, S.4    Geissler, L.A.5    Gregoire, S.L.6    Nguyen, H.H.7    Moore, E.C.8    Tanaka, W.K.9
  • 9
    • 0001250044 scopus 로고
    • Pathogenesis and Treatment of Alopecias
    • Gadwood, R. C.; Fiedler, V. C. Pathogenesis and Treatment of Alopecias. Annu. Rep. Med. Chem. 1989, 24, 187-196.
    • (1989) Annu. Rep. Med. Chem. , vol.24 , pp. 187-196
    • Gadwood, R.C.1    Fiedler, V.C.2
  • 10
    • 0022914824 scopus 로고
    • Treatment of Hirsutism with 5α-Reductase Inhibitors
    • Brooks, J. R. Treatment of Hirsutism with 5α-Reductase Inhibitors. Clin. Endocrinol. Metabol. 1986, 15, 391-405.
    • (1986) Clin. Endocrinol. Metabol. , vol.15 , pp. 391-405
    • Brooks, J.R.1
  • 11
    • 0024397969 scopus 로고
    • Inhibitors of Steroid 5α-Reductase in Benign Prostatic Hyperplasia, Male Pattern Baldness and Acne
    • Metcalf, B. W.; Levy, M. A.; Holt, D. A. Inhibitors of Steroid 5α-Reductase in Benign Prostatic Hyperplasia, Male Pattern Baldness and Acne. Trends Pharmacol. Sci. 1989, 10, 491-495.
    • (1989) Trends Pharmacol. Sci. , vol.10 , pp. 491-495
    • Metcalf, B.W.1    Levy, M.A.2    Holt, D.A.3
  • 12
    • 0003312869 scopus 로고
    • Inhibition of Steroid 5α-Reductase
    • Maryanoff, B. E., Maryanoff, C. A., Eds.; JAI Press Inc.: Greenwich, CT
    • (a) Holt, D. A.; Levy, M. A.; Metcalf, B. W. Inhibition of Steroid 5α-Reductase. In Advances in Medicinal Chemistry; Maryanoff, B. E., Maryanoff, C. A., Eds.; JAI Press Inc.: Greenwich, CT, 1993; Vol. 2, pp 1-29.
    • (1993) Advances in Medicinal Chemistry , vol.2 , pp. 1-29
    • Holt, D.A.1    Levy, M.A.2    Metcalf, B.W.3
  • 13
    • 0029038763 scopus 로고
    • Steroidal and Non-Steroidal Inhibitors of Steroid 5α-Reductase
    • (b) Abell, A. D.; Henderson, B. R. Steroidal and Non-Steroidal Inhibitors of Steroid 5α-Reductase. Curr. Med. Chem. 1995, 2, 583-597.
    • (1995) Curr. Med. Chem. , vol.2 , pp. 583-597
    • Abell, A.D.1    Henderson, B.R.2
  • 14
    • 0029055505 scopus 로고
    • The Enzyme and Inhibitors of 4-Ene-3-oxosteroid 5α-Oxidoreductase
    • (c) Li, X.; Chen, C.; Singh, S.; Labrie, F. The Enzyme and Inhibitors of 4-Ene-3-oxosteroid 5α-Oxidoreductase. Steroids 1995, 60, 430-441.
    • (1995) Steroids , vol.60 , pp. 430-441
    • Li, X.1    Chen, C.2    Singh, S.3    Labrie, F.4
  • 15
    • 0025644398 scopus 로고
    • Effect of Finasteride, a 5α-Reductase Inhibitor on Prostate Tissue Androgens and Prostate-Specific Antigen
    • (a) Geller, J. Effect of Finasteride, a 5α-Reductase Inhibitor on Prostate Tissue Androgens and Prostate-Specific Antigen. J. Clin. Endocrinol. Metab. 1990, 71, 1552-1555.
    • (1990) J. Clin. Endocrinol. Metab. , vol.71 , pp. 1552-1555
    • Geller, J.1
  • 16
    • 0025689849 scopus 로고
    • The Clinical Development of a 5α-Reductase Inhibitor, Finasteride
    • (b) Stoner, E. The Clinical Development of a 5α-Reductase Inhibitor, Finasteride. J. Steroid Biochem. Mol. Biol. 1990, 37, 375-378.
    • (1990) J. Steroid Biochem. Mol. Biol. , vol.37 , pp. 375-378
    • Stoner, E.1
  • 17
    • 0026806486 scopus 로고
    • The Effect of Finasteride in Men with Benign Prostatic Hyperplasia
    • (c) Gormley, G. J.; et al. The Effect of Finasteride in Men with Benign Prostatic Hyperplasia. New Engl. J. Med. 1992, 327, 1185-1191.
    • (1992) New Engl. J. Med. , vol.327 , pp. 1185-1191
    • Gormley, G.J.1
  • 20
    • 0027414963 scopus 로고
    • Azasteroids as Inhibitors of Testosterone 5α-Reductase in Mammalian Skin
    • (c) Mellin, T. N.; Busch, R. D.; Rasmusson, G. H. Azasteroids as Inhibitors of Testosterone 5α-Reductase in Mammalian Skin. J. Steroid Biochem. Mol. Biol. 1993, 44, 121-131.
    • (1993) J. Steroid Biochem. Mol. Biol. , vol.44 , pp. 121-131
    • Mellin, T.N.1    Busch, R.D.2    Rasmusson, G.H.3
  • 23
    • 0001040796 scopus 로고
    • Effect of Multiple Doses of Epristeride, a Steroid 5α-Reductase Inhibitor, on Serum Dihydrotestosterone in Older Male Subjects
    • (b) Audet, P.; Nurcombe, H.; Lamb, Y.; Yorkasky, D.; Loyd-Davies, K.; Morris, R. Effect of Multiple Doses of Epristeride, a Steroid 5α-Reductase Inhibitor, on Serum Dihydrotestosterone in Older Male Subjects. Clin. Pharmacol. Ther. 1993, 53, 231.
    • (1993) Clin. Pharmacol. Ther. , vol.53 , pp. 231
    • Audet, P.1    Nurcombe, H.2    Lamb, Y.3    Yorkasky, D.4    Loyd-Davies, K.5    Morris, R.6
  • 26
    • 0025366342 scopus 로고
    • Inhibition of Rat Liver Steroid 5α-Reductase by 3-Androstene-3-carboxylic Acid: Mechanism of Enzyme-Inhibitor Interaction
    • (b) Levy, M. A.; Brandt, M.; Heys, J. R.; Holt, D. A.; Metcalf, B. W. Inhibition of Rat Liver Steroid 5α-Reductase by 3-Androstene-3-carboxylic Acid: Mechanism of Enzyme-Inhibitor Interaction. Biochemistry 1990, 29, 2815-2824.
    • (1990) Biochemistry , vol.29 , pp. 2815-2824
    • Levy, M.A.1    Brandt, M.2    Heys, J.R.3    Holt, D.A.4    Metcalf, B.W.5
  • 27
    • 23444459401 scopus 로고
    • Drug Therapy: Finasteride
    • (a) Rittmaster, R. S. Drug Therapy: Finasteride. New Engl. J. Med. 1994, 330, 120-125.
    • (1994) New Engl. J. Med. , vol.330 , pp. 120-125
    • Rittmaster, R.S.1
  • 28
    • 0027965712 scopus 로고
    • Effect of Finasteride on Adrenal Steroidogenesis in Men
    • (b) Rittmaster, R. S.; Antonian, L.; New, M. I.; Stoner, E. Effect of Finasteride on Adrenal Steroidogenesis in Men. J. Androl. 1994, 15, 298-301.
    • (1994) J. Androl. , vol.15 , pp. 298-301
    • Rittmaster, R.S.1    Antonian, L.2    New, M.I.3    Stoner, E.4
  • 31
    • 0023185333 scopus 로고
    • The Effects of N,N-Diethyl-4-Methyl-3-Oxo-4-Aza-5α-Androstane-17β-Carboxamide, a 5α-Reductase Inhibitor and Antiandrogen, on the Development of Baldness in the Stumptail Macaque
    • (a) Rittmaster, R. S.; Uno, H.; Povar, M. L.; Mellin, T. N.; Loriaux, D. L. The Effects of N,N-Diethyl-4-Methyl-3-Oxo-4-Aza-5α-Androstane-17β-Carboxamide, a 5α-Reductase Inhibitor and Antiandrogen, on the Development of Baldness in the Stumptail Macaque. J. Clin. Endocrinol. Metab. 1987, 65, 188-193.
    • (1987) J. Clin. Endocrinol. Metab. , vol.65 , pp. 188-193
    • Rittmaster, R.S.1    Uno, H.2    Povar, M.L.3    Mellin, T.N.4    Loriaux, D.L.5
  • 32
    • 0029101544 scopus 로고
    • Activity of the Type 1 5α-Reductase Exhibits Regional Differences in Isolated Sebaceous Glands and Whole Skin
    • (b) Thiboutot, D.; Harris, G.; Iles, V.; Cimis, G.; Gilliland, K.; Hagari, S. Activity of the Type 1 5α-Reductase Exhibits Regional Differences in Isolated Sebaceous Glands and Whole Skin. J. Invest. Dermatol. 1995, 105, 209-214.
    • (1995) J. Invest. Dermatol. , vol.105 , pp. 209-214
    • Thiboutot, D.1    Harris, G.2    Iles, V.3    Cimis, G.4    Gilliland, K.5    Hagari, S.6
  • 34
    • 0028806780 scopus 로고
    • Finasteride: A Clinical Review
    • Gormley, G. J. Finasteride: a Clinical Review. Biomed. Pharmacother. 1995, 49, 319-324.
    • (1995) Biomed. Pharmacother. , vol.49 , pp. 319-324
    • Gormley, G.J.1
  • 36
    • 0001053981 scopus 로고
    • Rearrangement of Isoxazoline-5-Spiro Derivatives. 1. Synthesis of 4,5-Dihydroisoxazole-5-spirocyclopropanes and Their Rearrangement to 5,6-Dihydro-4-pyridones
    • (a) Guarna, A.; Brandi, A.; De Sarlo, F.; Goti, A.; Pericciuoli, F. Rearrangement of Isoxazoline-5-Spiro Derivatives. 1. Synthesis of 4,5-Dihydroisoxazole-5-spirocyclopropanes and Their Rearrangement to 5,6-Dihydro-4-pyridones. J. Org. Chem. 1988, 53, 2426-2429.
    • (1988) J. Org. Chem. , vol.53 , pp. 2426-2429
    • Guarna, A.1    Brandi, A.2    De Sarlo, F.3    Goti, A.4    Pericciuoli, F.5
  • 37
    • 85023437495 scopus 로고
    • New Synthesis of Azaheterocycles by Rearrangement of Isoxazoline-5-Spirocycloalkane Compounds
    • (b) Brandi, A.; Cordero, F. M.; De Sarlo, F.; Goti, A.; Guarna, A. New Synthesis of Azaheterocycles by Rearrangement of Isoxazoline-5-Spirocycloalkane Compounds. Synlett 1993, 1-8.
    • (1993) Synlett , pp. 1-8
    • Brandi, A.1    Cordero, F.M.2    De Sarlo, F.3    Goti, A.4    Guarna, A.5
  • 39
    • 0001186945 scopus 로고
    • N-Bridgehead Polycyclic Compounds by Sequential Rearrangement-Annulation of Isoxazoline-5-Spirocyclopropanes. 6. A General Synthetic Method for 5,6-Dihydro-7(8H)- and 2,3,5,6-Tetrahydro-7(1H)-indolizinones
    • Occhiato, E.; Guarna, A.; Brandi, A.; Goti, A.; De Sarlo, F. N-Bridgehead Polycyclic Compounds by Sequential Rearrangement-Annulation of Isoxazoline-5-Spirocyclopropanes. 6. A General Synthetic Method for 5,6-Dihydro-7(8H)-and 2,3,5,6-Tetrahydro-7(1H)-indolizinones. J. Org. Chem. 1992, 57, 4206-4211.
    • (1992) J. Org. Chem. , vol.57 , pp. 4206-4211
    • Occhiato, E.1    Guarna, A.2    Brandi, A.3    Goti, A.4    De Sarlo, F.5
  • 41
    • 15144342865 scopus 로고
    • New Aspects of the Catalytic Hydrogenation of 2,3,5,6,7,7a-Hexahydro-1β-hydroxy-7aβ-methyl-5-oxo-1H-indene-4- Propionic Acid, an Important Intermediate in the Total Synthesis of Steroids
    • Belle, C.; Guarna, A.; Paoli, P.; Dapporto, P. New Aspects of the Catalytic Hydrogenation of 2,3,5,6,7,7a-Hexahydro-1β-hydroxy-7aβ-methyl-5-oxo-1H-indene-4- Propionic Acid, an Important Intermediate in the Total Synthesis of Steroids. J. Chem. Res. 1992, 122-123.
    • (1992) J. Chem. Res. , pp. 122-123
    • Belle, C.1    Guarna, A.2    Paoli, P.3    Dapporto, P.4
  • 42
    • 15144345203 scopus 로고    scopus 로고
    • U.S. Pat. 4 062 729, 1977
    • Biggs, C. B.; Pyke, T. R.; Wovcha, M. G. (Upjhon Co.). U.S. Pat. 4 062 729, 1977; Chem. Abstr. 1978, 88, 188129t.
    • Biggs, C.B.1    Pyke, T.R.2    Wovcha, M.G.3
  • 43
    • 15144353741 scopus 로고    scopus 로고
    • Biggs, C. B.; Pyke, T. R.; Wovcha, M. G. (Upjhon Co.). U.S. Pat. 4 062 729, 1977; Chem. Abstr. 1978, 88, 188129t.
    • Chem. Abstr. , vol.1978 , pp. 88
  • 44
    • 0006458732 scopus 로고
    • Perchloric Acid Catalyzed Acetylations. Enol Lactonization and Enol Acetylation of Steroids
    • Edward, B. E.; Rao, P. N. Perchloric Acid Catalyzed Acetylations. Enol Lactonization and Enol Acetylation of Steroids. J. Org. Chem. 1966, 3, 324-327.
    • (1966) J. Org. Chem. , vol.3 , pp. 324-327
    • Edward, B.E.1    Rao, P.N.2
  • 45
    • 15144342032 scopus 로고
    • Thiosteroids-XXXIH 10β-Methylsulfonyl and 10β-Phenylsulfonyl Des-A-Estr-9(11)-ene Derivatives and Their Alkylation Reaction: Synthesis of A-Furanosteroids
    • Komeno, T.; Ishihara, S.; Itani, H. Thiosteroids-XXXIH 10β-Methylsulfonyl and 10β-Phenylsulfonyl Des-A-Estr-9(11)-ene Derivatives and Their Alkylation Reaction: Synthesis of A-Furanosteroids. Tetrahedron 1972, 28, 4719-4736.
    • (1972) Tetrahedron , vol.28 , pp. 4719-4736
    • Komeno, T.1    Ishihara, S.2    Itani, H.3
  • 46
    • 84989044980 scopus 로고
    • Synthesis of 1-(Ethynyl)-vinyl Trifluoromethansulfonates
    • (a) Stang, P. J.; Fisk, T. E. Synthesis of 1-(Ethynyl)-vinyl Trifluoromethansulfonates. Synthesis 1979, 438-440.
    • (1979) Synthesis , pp. 438-440
    • Stang, P.J.1    Fisk, T.E.2
  • 47
    • 0000311627 scopus 로고
    • Palladium-catalyzed Carbonylation of Enol Triflates. A Novel Method for One-Carbon Homologation of Ketones to α,β-Unsaturated Carboxylic Acid
    • (b) Cacchi, S.; Morera, E.; Ortar, G. Palladium-catalyzed Carbonylation of Enol Triflates. A Novel Method for One-Carbon Homologation of Ketones to α,β-Unsaturated Carboxylic Acid. Tetrahedron Lett. 1985, 26, 2965, 2966.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 2965
    • Cacchi, S.1    Morera, E.2    Ortar, G.3
  • 48
    • 15144345002 scopus 로고
    • Wet Silica Gel; a Convenient Reagent for Deacetylization
    • Huet, F.; Lechevallier, A.; Pellet, M.; Conia, J. M. Wet Silica Gel; a Convenient Reagent for Deacetylization. Synthesis 1979, 725.
    • (1979) Synthesis , pp. 725
    • Huet, F.1    Lechevallier, A.2    Pellet, M.3    Conia, J.M.4
  • 49
    • 0000699576 scopus 로고
    • A Simplified Synthesis of Unsaturated Nitrogen-Heterocycles using Nitrile Betaines
    • Lee, G. A. A Simplified Synthesis of Unsaturated Nitrogen-Heterocycles using Nitrile Betaines. Synthesis 1982, 508.
    • (1982) Synthesis , pp. 508
    • Lee, G.A.1
  • 50
    • 0008529757 scopus 로고
    • The Influence of Steric and Torsional Strain on the Steric Course of Additions to Cyclohexanones. The Reaction between 4-t-Butylcyclohexanone and t-Butylallyl Magnesium Bromide
    • Cherest, M.; Felkin, H. The Influence of Steric and Torsional Strain on the Steric Course of Additions to Cyclohexanones. The Reaction between 4-t-Butylcyclohexanone and t-Butylallyl Magnesium Bromide. Tetrahedron Lett. 1971, 383.
    • (1971) Tetrahedron Lett. , pp. 383
    • Cherest, M.1    Felkin, H.2
  • 51
    • 15144355727 scopus 로고
    • Berlin, Germany, Sept. 29-Oct 1
    • Results presented at the Second European Congress of Pharmaceutical Sciences, Berlin, Germany, Sept. 29-Oct 1, 1994. Guarna, A.; Marrucci, A.; Danza, G.; Serio, M. Structure-Activity Relationship of Inhibitors for Steroid 5α-Reductase. Eur. J. Pharm. Sci. 1994, 2, 91.
    • (1994) Second European Congress of Pharmaceutical Sciences
  • 52
    • 15144355727 scopus 로고
    • Structure-Activity Relationship of Inhibitors for Steroid 5α-Reductase
    • Results presented at the Second European Congress of Pharmaceutical Sciences, Berlin, Germany, Sept. 29-Oct 1, 1994. Guarna, A.; Marrucci, A.; Danza, G.; Serio, M. Structure-Activity Relationship of Inhibitors for Steroid 5α-Reductase. Eur. J. Pharm. Sci. 1994, 2, 91.
    • (1994) Eur. J. Pharm. Sci. , vol.2 , pp. 91
    • Guarna, A.1    Marrucci, A.2    Danza, G.3    Serio, M.4
  • 53
    • 0027436151 scopus 로고
    • Enantioselective Synthesis of Indolizine Derivatives by Rearrangement-Cyclization of Isoxazoline-5-spirocyclopropanes
    • and references cited therein
    • Oechiato, E. G.; Guarna, A.; Spinetti, L. M. Enantioselective Synthesis of Indolizine Derivatives by Rearrangement-Cyclization of Isoxazoline-5-spirocyclopropanes. Tetrahedron 1993, 49, 10629-10642 and references cited therein.
    • (1993) Tetrahedron , vol.49 , pp. 10629-10642
    • Oechiato, E.G.1    Guarna, A.2    Spinetti, L.M.3
  • 54
    • 0001694460 scopus 로고
    • Stereochemical Studies of Nitrogen Bridgehead Compounds by Spectral Means
    • (a) Crabb, T. A.; Newton, R. F.; Jackson, D. Stereochemical Studies of Nitrogen Bridgehead Compounds by Spectral Means. Chem. Rev. 1971, 71, 109-126.
    • (1971) Chem. Rev. , vol.71 , pp. 109-126
    • Crabb, T.A.1    Newton, R.F.2    Jackson, D.3
  • 55
    • 0000491729 scopus 로고
    • Stereochemistry, Conformational Analysis and Transannular Cyclisation of Nine-Membered Ring Azaolefins
    • (b) Wilson, S. R.; Sawicki, R. A. Stereochemistry, Conformational Analysis and Transannular Cyclisation of Nine-Membered Ring Azaolefins. J. Org. Chem. 1979, 44, 330-336.
    • (1979) J. Org. Chem. , vol.44 , pp. 330-336
    • Wilson, S.R.1    Sawicki, R.A.2
  • 57
    • 0014439944 scopus 로고
    • Synthèse de Stéroides Hétérocycliques. L'Aza-10 nor-19 Testostérone de Configuration Naturelle
    • Bertin, D.; Perronet, J. Synthèse de Stéroides Hétérocycliques. L'Aza-10 nor-19 Testostérone de Configuration Naturelle. (Synthesis of Heterocycle Steroids. 19-Nor-10-aza-Testosterone with Natural Configuration.) Bull. Soc. Chim. (France) 1969, 117-122.
    • (1969) Bull. Soc. Chim. (France) , pp. 117-122
    • Bertin, D.1    Perronet, J.2
  • 58
    • 0022390704 scopus 로고
    • Species Differences in Prostatic Steroid 5α-Reductases of Rat, Dog, and Human
    • (a) Liang, T.; Cascieri, M. A.; Cheung, A. H.; Reynolds, G. F.; Rasmusson, G. H. Species Differences in Prostatic Steroid 5α-Reductases of Rat, Dog, and Human. Endocrinology 1985, 117, 571-579.
    • (1985) Endocrinology , vol.117 , pp. 571-579
    • Liang, T.1    Cascieri, M.A.2    Cheung, A.H.3    Reynolds, G.F.4    Rasmusson, G.H.5
  • 59
    • 0024851536 scopus 로고
    • 4-3-Ketosteroid (5α) Reductase Inhibitors
    • 4-3-Ketosteroid (5α) Reductase Inhibitors. Chem. Pharm. Bull. 1989, 37, 3128-3130.
    • (1989) Chem. Pharm. Bull. , vol.37 , pp. 3128-3130
    • Komoda, Y.1
  • 61
    • 0023680233 scopus 로고
    • Kinetic Parameters of 5α-Reductase Activity in Stroma and Epithelium of Normal, Hyperplastic and Carcinomatous Human Prostates
    • (a) Bruchovsky, N.; Rennie, P. S.; Batzold, F. K.; Goldenberg, S. L.; Fletcher, T.; McLoughlin, M. G. Kinetic Parameters of 5α-Reductase Activity in Stroma and Epithelium of Normal, Hyperplastic and Carcinomatous Human Prostates. J. Clin. Endocrinol. Metab. 1988, 67, 806-816.
    • (1988) J. Clin. Endocrinol. Metab. , vol.67 , pp. 806-816
    • Bruchovsky, N.1    Rennie, P.S.2    Batzold, F.K.3    Goldenberg, S.L.4    Fletcher, T.5    McLoughlin, M.G.6
  • 62
    • 0023624754 scopus 로고
    • A Kinetic Analysis of the 5α-Reductases from Human Prostate and Liver
    • (b) Houston, B.; Chisholm, G. D.; Habib, F. K. A Kinetic Analysis of the 5α-Reductases from Human Prostate and Liver. Steroids 1987, 49, 355-369.
    • (1987) Steroids , vol.49 , pp. 355-369
    • Houston, B.1    Chisholm, G.D.2    Habib, F.K.3
  • 63
    • 0028670397 scopus 로고
    • Purification of Testosterone 5α-Reductase from Human Prostate by a Four-Step Chromatographic Procedure
    • (c) Quemener, E.; Amet, Y.; di Stefano, S.; Fournier, G.; Floch, H. H.; Abalain, J. H. Purification of Testosterone 5α-Reductase from Human Prostate by a Four-Step Chromatographic Procedure. Steroids 1994, 59, 712-718.
    • (1994) Steroids , vol.59 , pp. 712-718
    • Quemener, E.1    Amet, Y.2    Di Stefano, S.3    Fournier, G.4    Floch, H.H.5    Abalain, J.H.6
  • 64
    • 0030005247 scopus 로고    scopus 로고
    • Kinetic Analysis of Steroid 5α-Reductase Activity at Neutral pH in Benign Prostatic Hyperplastic Tissue: Evidence for Type I Isoenzyme Activity in the Human Prostate
    • Span, P. N.; Benraad, T. J.; Sweep, C. G. J.; Smals, A. G. H. Kinetic Analysis of Steroid 5α-Reductase Activity at Neutral pH In Benign Prostatic Hyperplastic Tissue: Evidence for Type I Isoenzyme Activity in the Human Prostate. J. Steroid Biochem. Mol. Biol. 1996, 57, 103-108.
    • (1996) J. Steroid Biochem. Mol. Biol. , vol.57 , pp. 103-108
    • Span, P.N.1    Benraad, T.J.2    Sweep, C.G.J.3    Smals, A.G.H.4
  • 65
    • 15144344526 scopus 로고    scopus 로고
    • note
    • 37a,44,48 For a recent comparison of finasteride inhibition potency toward types 1 and 2 isozymes expressed in a different system, see ref 48.
  • 66
    • 0028053885 scopus 로고
    • 5α-Reductase Inhibition by Finasteride (Proscar) in Epithelium and Stroma of Human Benign Prostatic Hyperplasia
    • Weisser, H.; Tunn, S.; Debus, M.; Krieg, M. 5α-Reductase Inhibition by Finasteride (Proscar) in Epithelium and Stroma of Human Benign Prostatic Hyperplasia. Steroids 1994, 59, 616-620.
    • (1994) Steroids , vol.59 , pp. 616-620
    • Weisser, H.1    Tunn, S.2    Debus, M.3    Krieg, M.4
  • 68
    • 0026055914 scopus 로고
    • Deletion of Steroid 5α-Reductase 2 Gene in Male Pseudohermaphroditism
    • Andersson, S.; Berman, D. M.; Jenkins, E. P.; Russell, D. W. Deletion of Steroid 5α-Reductase 2 Gene in Male Pseudohermaphroditism. Nature (London) 1991, 354, 159-161.
    • (1991) Nature (London) , vol.354 , pp. 159-161
    • Andersson, S.1    Berman, D.M.2    Jenkins, E.P.3    Russell, D.W.4
  • 70
    • 0027248515 scopus 로고
    • Characterization of Chinese Hamster Ovary Cell Lines Expressing Human Steroid 5α-Reductase Isozymes
    • Thigpen, A. E.; Cala, K. M.; Russell, D. W. Characterization of Chinese Hamster Ovary Cell Lines Expressing Human Steroid 5α-Reductase Isozymes. J. Biol. Chem. 1993, 268, 17404-17412.
    • (1993) J. Biol. Chem. , vol.268 , pp. 17404-17412
    • Thigpen, A.E.1    Cala, K.M.2    Russell, D.W.3
  • 72
    • 0029926673 scopus 로고    scopus 로고
    • 5α-Reductase Expression by Prostate Cancer Cell Lines and Benign Prostatic Hyperplasia in Vitro
    • Smith, C. M.; Ballard, S. A.; Worman, N.; Buettner, R.; Masters, J. R. W. 5α-Reductase Expression by Prostate Cancer Cell Lines and Benign Prostatic Hyperplasia in Vitro. J. Clin. Endocrinol. Metab. 1996, 81, 1361-1366.
    • (1996) J. Clin. Endocrinol. Metab. , vol.81 , pp. 1361-1366
    • Smith, C.M.1    Ballard, S.A.2    Worman, N.3    Buettner, R.4    Masters, J.R.W.5
  • 73
    • 0028301655 scopus 로고
    • Inhibition of the Activity of 'Basic' 5α- Reductase (Type 1) Detected in du 145 Cells and Expressed in Insect Cells
    • Delos, S.; Iehlé, C.; Martin, M.; Raynaud, J.-P. Inhibition of the Activity of 'Basic' 5α-Reductase (Type 1) Detected in DU 145 Cells and Expressed in Insect Cells. J. Steroid Biochem. Mol. Biol. 1994, 48, 347-352.
    • (1994) J. Steroid Biochem. Mol. Biol. , vol.48 , pp. 347-352
    • Delos, S.1    Iehlé, C.2    Martin, M.3    Raynaud, J.-P.4
  • 74
    • 3042981033 scopus 로고    scopus 로고
    • Characterization of Type I 5α-Reductase Activity in DU145 Human Prostatic Adenocarcinoma Cells
    • Kaefer, M.; Audia, J. E.; Bruchovsky, N.; et al. Characterization of Type I 5α-Reductase Activity in DU145 Human Prostatic Adenocarcinoma Cells. J. Steroid Biochem. Mol. Biol. 1996, 58, 195-205.
    • (1996) J. Steroid Biochem. Mol. Biol. , vol.58 , pp. 195-205
    • Kaefer, M.1    Audia, J.E.2    Bruchovsky, N.3
  • 75
    • 0028906285 scopus 로고
    • Synthesis and in Vitro Activity of 17β-(N-Alkyl/arylformamido) and 17β-(N-alkyl/arylalkyl/arylamido)-4-methyl-4-aza-3-oxo-5α-androstan- 3-ones as Inhibitors of Human 5α-Reductases and Antagonists of the Androgen Receptor
    • Li, X.; Singh, S. M.; Labrie, F. Synthesis and in Vitro Activity of 17β-(N-Alkyl/arylformamido) and 17β-(N-alkyl/arylalkyl/arylamido)-4-methyl-4-aza-3-oxo-5α-androstan- 3-ones as Inhibitors of Human 5α-Reductases and Antagonists of the Androgen Receptor. J. Med. Chem. 1995, 38, 1158-1173.
    • (1995) J. Med. Chem. , vol.38 , pp. 1158-1173
    • Li, X.1    Singh, S.M.2    Labrie, F.3
  • 76
    • 0002903441 scopus 로고
    • Analog Approaches to the Structure of the Transition Sate in Enzyme Reactions
    • Wolfenden, R. Analog Approaches to the Structure of the Transition Sate in Enzyme Reactions. Acc. Chem. Res. 1972, 5, 10-18.
    • (1972) Acc. Chem. Res. , vol.5 , pp. 10-18
    • Wolfenden, R.1
  • 77
    • 0029937631 scopus 로고    scopus 로고
    • Mechanism-Based Inhibition of Human Steroid 5α-Reductase by Finasteride: Enzyme-Catalyzed Formation of NADP-Dihydrofinasteride, a Potent Bisubstrate Analog Inhibitor
    • Bull, H. G.; Garcia-Calvo, M.; Andersson, S.; et al. Mechanism-Based Inhibition of Human Steroid 5α-Reductase by Finasteride: Enzyme-Catalyzed Formation of NADP-Dihydrofinasteride, a Potent Bisubstrate Analog Inhibitor. J. Am. Chem. Soc. 1996, 118, 2359-2365.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 2359-2365
    • Bull, H.G.1    Garcia-Calvo, M.2    Andersson, S.3
  • 78
    • 0029986010 scopus 로고    scopus 로고
    • Vinyl Fluoride as a Mimic of the 'Intermediate' Enol Form in the 5α-Reductase Transformation: Synthesis and in Vitro Activity of (N-1′,1′-Dimethylethyl)-3-haloandrosta-3,5-diene-17β- Carboxamides
    • Li, X.; Singh, S. M.; Luu-The, V.; Côté, J.; Laplante, S.; Labrie, F. Vinyl Fluoride as a Mimic of the 'Intermediate' Enol Form In The 5α-Reductase Transformation: Synthesis and in Vitro Activity of (N-1′,1′-Dimethylethyl)-3-haloandrosta-3,5-diene-17β- Carboxamides. Bioorg. Med. Chem. 1996, 4, 55-60.
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 55-60
    • Li, X.1    Singh, S.M.2    Luu-The, V.3    Côté, J.4    Laplante, S.5    Labrie, F.6
  • 79
    • 15144350531 scopus 로고    scopus 로고
    • note
    • HF-STO3-21G* basis set calculations were performed by using the program SPARTAN, version 3.1, Wavefunction Inc., 18401 Von Karman Ave, 370, Irvine, CA 92715.
  • 80
    • 15144352992 scopus 로고    scopus 로고
    • note
    • 8(9)-19-nor-10-azasteroids are quite flexible molecules having four low-energy conformers within the 3 kcal/mol range above the global energy minimum.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.