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Volumn 23, Issue 1, 2005, Pages 46-57

Nonsteroidal progesterone receptor modulators: Structure activity relationships

Author keywords

Contraception; Endometriosis; Hormone therapy; PR agonists; PR antagonists; Progesterone receptor (PR); Uterine fibroids

Indexed keywords

ANTIGESTAGEN; BENZIMIDAZOLE 2 THIONES; BENZIMIDAZOLE DERIVATIVE; BENZOXAZINE DERIVATIVE; ESTROGEN; GESTAGEN; NONSTEROIDAL PROGESTERONE AGONIST; NONSTEROIDAL PROGESTERONE ANTAGONIST; PROGESTERONE; PROGESTERONE RECEPTOR; STEROID RECEPTOR; UNCLASSIFIED DRUG;

EID: 14744298376     PISSN: 15268004     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-864033     Document Type: Review
Times cited : (25)

References (46)
  • 3
    • 0034992739 scopus 로고    scopus 로고
    • Relief of vasomotor symptoms and vaginal atrophy with lower doses of conjugated equine estrogens and medroxyprogesterone acetate
    • Utian WH, Shoupe D, Bachmann G, Pinkerton JV, Pickar JH. Relief of vasomotor symptoms and vaginal atrophy with lower doses of conjugated equine estrogens and medroxyprogesterone acetate. Fertil Steril 2001;75:1065-1079
    • (2001) Fertil Steril , vol.75 , pp. 1065-1079
    • Utian, W.H.1    Shoupe, D.2    Bachmann, G.3    Pinkerton, J.V.4    Pickar, J.H.5
  • 4
    • 0035854025 scopus 로고    scopus 로고
    • Hormone replacement therapy and prevention of nonvertebral fractures: A metaanalysis of randomized trials
    • Torgerson DJ, Bell-Syer SEM. Hormone replacement therapy and prevention of nonvertebral fractures: a metaanalysis of randomized trials. JAMA 2001;285:2891-2897
    • (2001) JAMA , vol.285 , pp. 2891-2897
    • Torgerson, D.J.1    Bell-Syer, S.E.M.2
  • 5
    • 0029839856 scopus 로고    scopus 로고
    • Depot medroxyprogesterone acetate versus an oral contraceptive combined with very-low-dose danazol for long-term treatment of pelvic pain associated with endometriosis
    • Vercellini P, De Giorgi O, Oldani S, et al. Depot medroxyprogesterone acetate versus an oral contraceptive combined with very-low-dose danazol for long-term treatment of pelvic pain associated with endometriosis. Am J Obstet Gynecol 1996;175:396-401
    • (1996) Am J Obstet Gynecol , vol.175 , pp. 396-401
    • Vercellini, P.1    De Giorgi, O.2    Oldani, S.3
  • 6
    • 0032474679 scopus 로고    scopus 로고
    • The effects of self-administering emergency contraception
    • Glasier A, Baird D. The effects of self-administering emergency contraception. N Engl J Med 1998;339:1-4
    • (1998) N Engl J Med , vol.339 , pp. 1-4
    • Glasier, A.1    Baird, D.2
  • 7
    • 0027394348 scopus 로고
    • Mifepristone: A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential
    • Brogden RN, Goa KL, Faulds D. Mifepristone: a review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential. Drugs 1993;45:384-409
    • (1993) Drugs , vol.45 , pp. 384-409
    • Brogden, R.N.1    Goa, K.L.2    Faulds, D.3
  • 8
    • 0031913611 scopus 로고    scopus 로고
    • Chronic treatment of cycling rhesus monkeys with low doses of the antiprogestin ZK 137 316: Morphometric assessment of the uterus and oviduct
    • Slayden OD, Zelinski-Wooten MB, Chwalisz K, Stouffer RL, Brenner RM. Chronic treatment of cycling rhesus monkeys with low doses of the antiprogestin ZK 137 316: morphometric assessment of the uterus and oviduct. Hum Reprod 1998;13:269-277
    • (1998) Hum Reprod , vol.13 , pp. 269-277
    • Slayden, O.D.1    Zelinski-Wooten, M.B.2    Chwalisz, K.3    Stouffer, R.L.4    Brenner, R.M.5
  • 9
    • 0031913282 scopus 로고    scopus 로고
    • Chronic treatment of female rhesus monkeys with low doses of the antiprogestin ZK 137 316: Establishment of a regimen that permits normal menstrual cyclicity
    • Zelinski-Wooten MB, Slayden OD, Chwalisz K, et al. Chronic treatment of female rhesus monkeys with low doses of the antiprogestin ZK 137 316: establishment of a regimen that permits normal menstrual cyclicity. Hum Reprod 1998;13:259-267
    • (1998) Hum Reprod , vol.13 , pp. 259-267
    • Zelinski-Wooten, M.B.1    Slayden, O.D.2    Chwalisz, K.3
  • 10
    • 0028272514 scopus 로고
    • Clinical efficacy of the antiprogesterone RU486 in the treatment of endometriosis and uterine fibroids
    • Kettel LM, Murphy AA, Morales AJ, Yen SS. Clinical efficacy of the antiprogesterone RU486 in the treatment of endometriosis and uterine fibroids. Hum Reprod 1994;9(suppl 1):116-120
    • (1994) Hum Reprod , vol.9 , Issue.1 SUPPL. , pp. 116-120
    • Kettel, L.M.1    Murphy, A.A.2    Morales, A.J.3    Yen, S.S.4
  • 11
    • 0031777147 scopus 로고    scopus 로고
    • Preliminary report on the treatment of endometriosis with low-dose mifepristone (RU 486)
    • Kettel LM, Murphy AA, Morales AJ, Yen SS. Preliminary report on the treatment of endometriosis with low-dose mifepristone (RU 486). Am J Obstet Gynecol 1998;178:1151-1156
    • (1998) Am J Obstet Gynecol , vol.178 , pp. 1151-1156
    • Kettel, L.M.1    Murphy, A.A.2    Morales, A.J.3    Yen, S.S.4
  • 13
    • 0036050214 scopus 로고    scopus 로고
    • Anti-proliferative effects of progesterone antagonists in the primate endometrium: A potential role for the androgen receptor
    • Brenner RM, Slayden OD, Critchley HOD. Anti-proliferative effects of progesterone antagonists in the primate endometrium: a potential role for the androgen receptor. Reproduction 2002;124:167-172
    • (2002) Reproduction , vol.124 , pp. 167-172
    • Brenner, R.M.1    Slayden, O.D.2    Critchley, H.O.D.3
  • 14
    • 0037424683 scopus 로고    scopus 로고
    • Novel 6-aryl-1,4-dihydrobenzo[d]oxazine-2-thiones as potent, selective, and orally active nonsteroidal progesterone receptor agonists
    • Zhang P, Terefenko EA, Fensome A, et al. Novel 6-aryl-1,4-dihydrobenzo[d] oxazine-2-thiones as potent, selective, and orally active nonsteroidal progesterone receptor agonists. Bioorg Med Chem Lett 2003;13:1313-1316
    • (2003) Bioorg Med Chem Lett , vol.13 , pp. 1313-1316
    • Zhang, P.1    Terefenko, E.A.2    Fensome, A.3
  • 15
    • 0033673829 scopus 로고    scopus 로고
    • In vitro characterization of trimegestone: A new potent and selective progestin
    • Zhang Z, Lundeen SG, Zhu Y, Carver JM, Winneker RC. In vitro characterization of trimegestone: a new potent and selective progestin. Steroids 2000;65:637-643
    • (2000) Steroids , vol.65 , pp. 637-643
    • Zhang, Z.1    Lundeen, S.G.2    Zhu, Y.3    Carver, J.M.4    Winneker, R.C.5
  • 16
    • 0028922593 scopus 로고
    • Nonsteroidal human progesterone receptor modulators from the marine alga Cymopolia barbata
    • Pathirana C, Stein RB, Berger TS, et al. Nonsteroidal human progesterone receptor modulators from the marine alga Cymopolia barbata. Mol Pharmacol 1995;47:630-635
    • (1995) Mol Pharmacol , vol.47 , pp. 630-635
    • Pathirana, C.1    Stein, R.B.2    Berger, T.S.3
  • 17
    • 0032576697 scopus 로고    scopus 로고
    • Aryl-1,2-dihydrochromeno[3,4-f]quinolines: A novel class of nonsteroidal human progesterone receptor agonists
    • Zhi L, Tegley CM, Kallel EA, et al. Aryl-1,2-dihydrochromeno[3,4-f] quinolines: a novel class of nonsteroidal human progesterone receptor agonists. J Med Chem 1998;41:291-302
    • (1998) J Med Chem , vol.41 , pp. 291-302
    • Zhi, L.1    Tegley, C.M.2    Kallel, E.A.3
  • 18
    • 0034484857 scopus 로고    scopus 로고
    • Nonsteroidal progesterone receptor ligands with unprecedented receptor selectivity
    • Palmer S, Campen CA, Allan GF, et al. Nonsteroidal progesterone receptor ligands with unprecedented receptor selectivity. J Steroid Biochern Mol Biol 2000;75:33-42
    • (2000) J Steroid Biochern Mol Biol , vol.75 , pp. 33-42
    • Palmer, S.1    Campen, C.A.2    Allan, G.F.3
  • 19
    • 0019512134 scopus 로고
    • Differential effects of estradiol-17b and progesterone on the proliferation of glandular and luminal cells of rabbit uterine epithelium
    • Conti CJ, Gimenez-Conti IB, Zerbe GO, Gerschenson LE. Differential effects of estradiol-17b and progesterone on the proliferation of glandular and luminal cells of rabbit uterine epithelium. Biol Reprod 1981;24:643-648
    • (1981) Biol Reprod , vol.24 , pp. 643-648
    • Conti, C.J.1    Gimenez-Conti, I.B.2    Zerbe, G.O.3    Gerschenson, L.E.4
  • 20
    • 84944495442 scopus 로고
    • The assay of progestin
    • McPhail MK. The assay of progestin. J Physiol London 1934;83:145-156
    • (1934) J Physiol London , vol.83 , pp. 145-156
    • McPhail, M.K.1
  • 21
    • 0027964256 scopus 로고
    • Progesterone regulation of heparin-binding epidermal growth factor-like growth factor gene expression during sensitization and decidualization in the rat uterus: Effects of the antiprogestin, ZK 98. 99
    • Zhang Z, Funk C, Glasser SR, Mulholland J. Progesterone regulation of heparin-binding epidermal growth factor-like growth factor gene expression during sensitization and decidualization in the rat uterus: effects of the antiprogestin, ZK 98. 99. Endocrinology 1994;135:1256-1263
    • (1994) Endocrinology , vol.135 , pp. 1256-1263
    • Zhang, Z.1    Funk, C.2    Glasser, S.R.3    Mulholland, J.4
  • 22
    • 0034822884 scopus 로고    scopus 로고
    • Rat uterine complement C3 expression as a model for progesterone receptor modulators: Characterization of the new progestin trimegestone
    • Lundeen SG, Zhang Z, Zhu Y, Carver JM, Winneker RC. Rat uterine complement C3 expression as a model for progesterone receptor modulators: characterization of the new progestin trimegestone. J Steroid Biochem Mol Biol 2001;78:137-143
    • (2001) J Steroid Biochem Mol Biol , vol.78 , pp. 137-143
    • Lundeen, S.G.1    Zhang, Z.2    Zhu, Y.3    Carver, J.M.4    Winneker, R.C.5
  • 23
    • 0024363218 scopus 로고
    • Contraceptive potential of RU 486 by ovulation inhibition: I. Pituitary versus ovarian action with blockade of estrogen-induced endometrial proliferation
    • Van Uem JFHM, Hsiu JG, Chillik CF, et al. Contraceptive potential of RU 486 by ovulation inhibition: I. Pituitary versus ovarian action with blockade of estrogen-induced endometrial proliferation. Contraception 1989;40:171-184
    • (1989) Contraception , vol.40 , pp. 171-184
    • Van Uem, J.F.H.M.1    Hsiu, J.G.2    Chillik, C.F.3
  • 24
    • 0029073473 scopus 로고
    • Pharmacological properties of a new selective antiprogestagen: Org 33628
    • Kloosterboer HJ, Deckers GH, de Gooyer ME, et al. Pharmacological properties of a new selective antiprogestagen: Org 33628. Ann N Y Acad Sci 1995;761:192-201
    • (1995) Ann N Y Acad Sci , vol.761 , pp. 192-201
    • Kloosterboer, H.J.1    Deckers, G.H.2    De Gooyer, M.E.3
  • 25
    • 0033645769 scopus 로고    scopus 로고
    • Preclinical experience with two selective progesterone receptor modulators on breast and endometrium
    • Kloosterboer HJ, Deckers GH, Schoonen WGEJ, et al. Preclinical experience with two selective progesterone receptor modulators on breast and endometrium. Steroids 2000;65:733-740
    • (2000) Steroids , vol.65 , pp. 733-740
    • Kloosterboer, H.J.1    Deckers, G.H.2    Schoonen, W.G.E.J.3
  • 27
    • 0034611152 scopus 로고    scopus 로고
    • Nonsteroidal progesterone receptor antagonists based on 6-thiophenylhydroquinolines
    • Zhi L, Tegley CM, Pio B, et al. Nonsteroidal progesterone receptor antagonists based on 6-thiophenylhydroquinolines. Bioorg Med Chem Lett 2000;10:415-418
    • (2000) Bioorg Med Chem Lett , vol.10 , pp. 415-418
    • Zhi, L.1    Tegley, C.M.2    Pio, B.3
  • 28
    • 0037060909 scopus 로고    scopus 로고
    • Potent nonsteroidal progesterone receptor agonists: Synthesis and SAR study of 6-aryl benzoxazines
    • Zhang P, Terefenko EA, Fensome A, et al. Potent nonsteroidal progesterone receptor agonists: synthesis and SAR study of 6-aryl benzoxazines. Bioorg Med Chem Lett 2002;12:787-790
    • (2002) Bioorg Med Chem Lett , vol.12 , pp. 787-790
    • Zhang, P.1    Terefenko, E.A.2    Fensome, A.3
  • 29
    • 0027191140 scopus 로고
    • The progesterone antagonist RU486 acquires agonist activity upon stimulation of cAMP signaling pathways
    • Beck CA, Weigel NL, Moyer ML, Nordeen SK, Edwards DP. The progesterone antagonist RU486 acquires agonist activity upon stimulation of cAMP signaling pathways. Proc Natl Acad Sci USA 1993;90:4441-4445
    • (1993) Proc Natl Acad Sci USA , vol.90 , pp. 4441-4445
    • Beck, C.A.1    Weigel, N.L.2    Moyer, M.L.3    Nordeen, S.K.4    Edwards, D.P.5
  • 30
    • 0037424718 scopus 로고    scopus 로고
    • Novel 5-aryl-1,3-dihydro-indole-2-thiones: Potent, orally active progesterone receptor agonists
    • Fensome A, Koko M, Wrobel J, et al. Novel 5-aryl-1,3-dihydro-indole-2- thiones: potent, orally active progesterone receptor agonists. Bioorg Med Chem Lett 2003;13:1317-1320
    • (2003) Bioorg Med Chem Lett , vol.13 , pp. 1317-1320
    • Fensome, A.1    Koko, M.2    Wrobel, J.3
  • 31
    • 11144354665 scopus 로고    scopus 로고
    • Novel pyrrole-containing progesterone receptor modulators
    • Coffins MA, Hudak V, Bender R, et al. Novel pyrrole-containing progesterone receptor modulators. Bioorg Med Chem Lett 2004;14:2185-2189
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 2185-2189
    • Coffins, M.A.1    Hudak, V.2    Bender, R.3
  • 32
    • 0141678846 scopus 로고    scopus 로고
    • Benzylidene-1,2-dihydrochromeno[3,4-f]quinolines as selective progesterone receptor modulators
    • Zhi L, Tegley CM, Pio B, et al. Benzylidene-1,2-dihydrochromeno[3,4-f] quinolines as selective progesterone receptor modulators. J Med Chem 2003;46:4104-4112
    • (2003) J Med Chem , vol.46 , pp. 4104-4112
    • Zhi, L.1    Tegley, C.M.2    Pio, B.3
  • 33
    • 15144355008 scopus 로고    scopus 로고
    • Preparation, resolution, and biological evaluation of 5-aryl-1,2-dihydro-5H-chromeno[3,4-f]quinolines: Potent, orally active, nonsteroidal progesterone receptor agonists
    • Edwards JP, Zhi L, Pooley CLF, et al. Preparation, resolution, and biological evaluation of 5-aryl-1,2-dihydro-5H-chromeno[3,4-f]quinolines: potent, orally active, nonsteroidal progesterone receptor agonists. J Med Chem 1998;41:2779-2785
    • (1998) J Med Chem , vol.41 , pp. 2779-2785
    • Edwards, J.P.1    Zhi, L.2    Pooley, C.L.F.3
  • 34
    • 0032401093 scopus 로고    scopus 로고
    • Alkyl-1,2-dihydrochromeno[3,4-f]quinolines: A novel class of nonsteroidal progesterone receptor modulators
    • Zhi L, Tegley CM, Edwards JP, et al. Alkyl-1,2-dihydrochromeno[3,4-f] quinolines: a novel class of nonsteroidal progesterone receptor modulators. Bioorg Med Chem Lett 1998;8:3365-3370
    • (1998) Bioorg Med Chem Lett , vol.8 , pp. 3365-3370
    • Zhi, L.1    Tegley, C.M.2    Edwards, J.P.3
  • 35
    • 0038778433 scopus 로고    scopus 로고
    • Synthesis and biological activity of 5-methylidene 1,2-dihydrochromeno[3, 4-f]quinoline derivatives as progesterone receptor modulators
    • Zhi L, Tegley CM, Pio B, et al. Synthesis and biological activity of 5-methylidene 1,2-dihydrochromeno[3,4-f]quinoline derivatives as progesterone receptor modulators. Bioorg Med Chem Lett 2003;13:2071-2074
    • (2003) Bioorg Med Chem Lett , vol.13 , pp. 2071-2074
    • Zhi, L.1    Tegley, C.M.2    Pio, B.3
  • 36
    • 14444285263 scopus 로고    scopus 로고
    • PF1092A, B and C, new nonsteroidal progesterone receptor ligands produced by Penicillium oblatum. I. Taxonomy of producing strain, fermentation, isolation and biological activities
    • Tabata Y, Miike N, Hatsu M, et al. PF1092A, B and C, new nonsteroidal progesterone receptor ligands produced by Penicillium oblatum. I. Taxonomy of producing strain, fermentation, isolation and biological activities. J Antibiotics 1997;50:304-308
    • (1997) J Antibiotics , vol.50 , pp. 304-308
    • Tabata, Y.1    Miike, N.2    Hatsu, M.3
  • 37
    • 0037423075 scopus 로고    scopus 로고
    • CP8668, a novel orally active nonsteroidal progesterone receptor modulator with tetrahydrobenzindolone skeleton
    • Tabata Y, Iizuka Y, Shinei R, et al. CP8668, a novel orally active nonsteroidal progesterone receptor modulator with tetrahydrobenzindolone skeleton. Eur J Pharmacol 2003;461:73-78
    • (2003) Eur J Pharmacol , vol.461 , pp. 73-78
    • Tabata, Y.1    Iizuka, Y.2    Shinei, R.3
  • 38
    • 11144354332 scopus 로고    scopus 로고
    • Characterization of a new class of selective nonsteroidal progesterone receptor agonists
    • Dong Y, Roberge JY, Wang Z, et al. Characterization of a new class of selective nonsteroidal progesterone receptor agonists. Steroids 2004;69:201-217
    • (2004) Steroids , vol.69 , pp. 201-217
    • Dong, Y.1    Roberge, J.Y.2    Wang, Z.3
  • 39
    • 0032572837 scopus 로고    scopus 로고
    • Discovery and preliminary SAR studies of a novel, nonsteroidal progesterone receptor antagonist pharmacophore
    • Pooley CLF, Edwards JP, Goldman ME, et al. Discovery and preliminary SAR studies of a novel, nonsteroidal progesterone receptor antagonist pharmacophore. J Med Chem 1998;41:3461-3466
    • (1998) J Med Chem , vol.41 , pp. 3461-3466
    • Pooley, C.L.F.1    Edwards, J.P.2    Goldman, M.E.3
  • 40
    • 12444262282 scopus 로고    scopus 로고
    • Development of progesterone receptor antagonists from 1,2-dihydrochromeno[3,4-f]quinoline agonist pharmacophore
    • Zhi L, Ringgenberg JD, Edwards JP, et al. Development of progesterone receptor antagonists from 1,2-dihydrochromeno[3,4-f]quinoline agonist pharmacophore. Bioorg Med Chem Lett 2003;13:2075-2078
    • (2003) Bioorg Med Chem Lett , vol.13 , pp. 2075-2078
    • Zhi, L.1    Ringgenberg, J.D.2    Edwards, J.P.3
  • 41
    • 0032491268 scopus 로고    scopus 로고
    • Nonsteroidal progesterone receptor antagonists based on a conformationally-restricted subseries of 6-aryl-1,2-dihydro-2,2,4- trimethylquinolines
    • Hamann LG, Winn DT, Pooley CLF, et al. Nonsteroidal progesterone receptor antagonists based on a conformationally-restricted subseries of 6-aryl-1,2-dihydro-2,2,4-trimethylquinolines. Bioorg Med Chem Lett 1998;8:2731-2736
    • (1998) Bioorg Med Chem Lett , vol.8 , pp. 2731-2736
    • Hamann, L.G.1    Winn, D.T.2    Pooley, C.L.F.3
  • 42
    • 0035935207 scopus 로고    scopus 로고
    • Synthesis and progesterone receptor antagonist activities of 6-aryl benzimidazolones and benzothiazolones
    • Zhang P, Terefenko EA, Wrobel J, et al. Synthesis and progesterone receptor antagonist activities of 6-aryl benzimidazolones and benzothiazolones. Bioorg Med Chem Lett 2001;11:2747-2750
    • (2001) Bioorg Med Chem Lett , vol.11 , pp. 2747-2750
    • Zhang, P.1    Terefenko, E.A.2    Wrobel, J.3
  • 43
    • 18644369735 scopus 로고    scopus 로고
    • New progesterone receptor antagonists: 3,3-Disubstituted-S-aryloxindoles
    • Fensome A, Bender R, Cohen J, et al. New progesterone receptor antagonists: 3,3-disubstituted-S-aryloxindoles. Bioorg Med Chem Lett 2002;12:3487-3490
    • (2002) Bioorg Med Chem Lett , vol.12 , pp. 3487-3490
    • Fensome, A.1    Bender, R.2    Cohen, J.3
  • 44
    • 0037179638 scopus 로고    scopus 로고
    • Aryl-1,4-dihydrobenzo[d][1,3]oxazin-2-ones: A novel class of potent, selective, and orally active nonsteroidal progesterone receptor antagonists
    • Zhang P, Terefenko EA, Fensome A, et al. Aryl-1,4-dihydrobenzo[d][1,3] oxazin-2-ones: a novel class of potent, selective, and orally active nonsteroidal progesterone receptor antagonists. J Med Chem 2002;45:4379-4382
    • (2002) J Med Chem , vol.45 , pp. 4379-4382
    • Zhang, P.1    Terefenko, E.A.2    Fensome, A.3
  • 45
    • 0345735759 scopus 로고    scopus 로고
    • The preclinical biology of a new potent and selective progestin: Trimegestone
    • Winneker RC, Bitran D, Zhang Z. The preclinical biology of a new potent and selective progestin: trimegestone. Steroids 2003;68:915-920
    • (2003) Steroids , vol.68 , pp. 915-920
    • Winneker, R.C.1    Bitran, D.2    Zhang, Z.3
  • 46
    • 0028916048 scopus 로고
    • Anxiolytic effect of progesterone is mediated by the neurosteroid allopregnanolone at brain GABAA receptors
    • Bitran D, Shiekh M, McLeod M. Anxiolytic effect of progesterone is mediated by the neurosteroid allopregnanolone at brain GABAA receptors. J Neuroendocrinol 1995;7:171-177
    • (1995) J Neuroendocrinol , vol.7 , pp. 171-177
    • Bitran, D.1    Shiekh, M.2    McLeod, M.3


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