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Volumn 49, Issue 11, 2006, Pages 3056-3059

Novel chromene-derived selective estrogen receptor modulators useful for alleviating hot flushes and vaginal dryness

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPYRAN DERIVATIVE; CHOLESTEROL; CHROMENE DERIVATIVE; ETHINYLESTRADIOL; LY 357489; RALOXIFENE; SELECTIVE ESTROGEN RECEPTOR MODULATOR; UNCLASSIFIED DRUG;

EID: 33744791784     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060353u     Document Type: Article
Times cited : (47)

References (43)
  • 1
    • 0037435046 scopus 로고    scopus 로고
    • Antiestrogens and selective estrogen receptor modulators as multifunctional medicines., receptor interactions
    • For recent reviews, see the following: (a) Jordan, V. C. Antiestrogens and Selective Estrogen Receptor Modulators as Multifunctional Medicines., Receptor Interactions. J. Med. Chem. 2003, 46, 883-908.
    • (2003) J. Med. Chem. , vol.46 , pp. 883-908
    • Jordan, V.C.1
  • 2
    • 0037468902 scopus 로고    scopus 로고
    • Antiestrogens and selective estrogen receptor modulators as multifunctional medicines, clinical considerations and new agents
    • (b) Jordan, V. C. Antiestrogens and Selective Estrogen Receptor Modulators as Multifunctional Medicines, Clinical Considerations and New Agents. J. Med. Chem. 2003, 46, 1081-1111.
    • (2003) J. Med. Chem. , vol.46 , pp. 1081-1111
    • Jordan, V.C.1
  • 3
    • 0037434618 scopus 로고    scopus 로고
    • Selective estrogen-receptor modulators-mechanisms of action and application to clinical practice
    • (c) Riggs, B. L.; Hartmann, L. C. Selective Estrogen-Receptor Modulators-Mechanisms of Action and Application to Clinical Practice. N. Engl. J. Med. 2003, 348, 618-629.
    • (2003) N. Engl. J. Med. , vol.348 , pp. 618-629
    • Riggs, B.L.1    Hartmann, L.C.2
  • 4
    • 0034954706 scopus 로고    scopus 로고
    • Physiology of hot flashes
    • (d) Freedman, R. R. Physiology of Hot Flashes. Am. J. Hum. Biol. 2001, 13, 454-464.
    • (2001) Am. J. Hum. Biol. , vol.13 , pp. 454-464
    • Freedman, R.R.1
  • 7
    • 0036373440 scopus 로고    scopus 로고
    • SERMs: Evolutionary chemistry, revolutionary biology
    • (b) Miller, C. P. SERMs: Evolutionary Chemistry, Revolutionary Biology. Curr. Pharm. Des. 2002, 8 (23), 2089-2111
    • (2002) Curr. Pharm. Des. , vol.8 , Issue.23 , pp. 2089-2111
    • Miller, C.P.1
  • 8
    • 18844458270 scopus 로고    scopus 로고
    • SERMs: Evolutionary chemistry, revolutionary biology
    • (c) Kenemans, P.; Speroff, L. SERMs: Evolutionary Chemistry, Revolutionary Biology. Maturitas 2005, 51 (1), 21-28
    • (2005) Maturitas , vol.51 , Issue.1 , pp. 21-28
    • Kenemans, P.1    Speroff, L.2
  • 9
    • 13144295008 scopus 로고    scopus 로고
    • Acta obstetrician a study on urogenital complaints of postmenopausal women aged 50 and over
    • (d) Oskay, U. Y.; Beji, N. K.; Yalcin, O. Acta obstetrician A study on urogenital complaints of postmenopausal women aged 50 and over. Gynecol. Scand. 2005, 84 (1), 72-78.
    • (2005) Gynecol. Scand. , vol.84 , Issue.1 , pp. 72-78
    • Oskay, U.Y.1    Beji, N.K.2    Yalcin, O.3
  • 10
    • 0029586198 scopus 로고
    • Urogenital aging: An old problem newly recognized
    • (e) Bachmann G. Urogenital aging: an old problem newly recognized. Maturitas 1995, 22 Suppl S1-S5.
    • (1995) Maturitas , vol.22 , Issue.SUPPL.
    • Bachmann, G.1
  • 12
    • 0033649898 scopus 로고    scopus 로고
    • Selective estrogen receptor modulators (SERMs) in clinical practice
    • (b) Plouffe, L., Jr.; Facoq, C. M. Selective Estrogen Receptor Modulators (SERMs) in Clinical Practice. J. Soc. Gynecol. Invest. 2000, 7, S38-S46.
    • (2000) J. Soc. Gynecol. Invest. , vol.7
    • Plouffe Jr., L.1    Facoq, C.M.2
  • 13
    • 0032547326 scopus 로고    scopus 로고
    • Randomized trial of estrogen plus progestin for secondary prevention of coronary heart disease in postmenopausal women
    • (a) Hulley, S.; Grady, D.; Bush, T.; et al. Randomized Trial of Estrogen plus Progestin for Secondary Prevention of Coronary Heart Disease in Postmenopausal Women. J. Am. Med. Assoc. 1998, 280, 605-613.
    • (1998) J. Am. Med. Assoc. , vol.280 , pp. 605-613
    • Hulley, S.1    Grady, D.2    Bush, T.3
  • 14
    • 0030843969 scopus 로고    scopus 로고
    • Breast cancer and hormone replacement therapy
    • (b) Collaborative Group on Hormonal Factors in Breast Cancer. Breast Cancer and Hormone Replacement Therapy. Lancet 1997, 350, 1047-1059
    • (1997) Lancet , vol.350 , pp. 1047-1059
  • 17
    • 0033013227 scopus 로고    scopus 로고
    • Adverse events reported by postmenopausal women in controlled trials with raloxifene
    • (a) Davies, G. C.; Huster, M. W. J.; Lu, Y.; Plouffe, L., Jr.; Lakshmanan, M. Adverse Events Reported by Postmenopausal Women in Controlled Trials with Raloxifene. Obstet. Gynecol. 1999, 93, 558-565.
    • (1999) Obstet. Gynecol. , vol.93 , pp. 558-565
    • Davies, G.C.1    Huster, M.W.J.2    Lu, Y.3    Plouffe Jr., L.4    Lakshmanan, M.5
  • 19
    • 33744816435 scopus 로고    scopus 로고
    • Preparation of tetracyclic heterocycles as selective estrogen receptor modulators (SERMs) WO 2003053977, 2003. US 71997520031121, 2004
    • Kanojia, R. M.; Jain, N. F.; Ng, R.; Sui, Z.; Xu, J. Preparation of tetracyclic heterocycles as selective estrogen receptor modulators (SERMs) WO 2003053977, 2003. US 71997520031121, 2004.
    • Kanojia, R.M.1    Jain, N.F.2    Ng, R.3    Sui, Z.4    Xu, J.5
  • 20
    • 3242810437 scopus 로고    scopus 로고
    • Preparation of tetracyclic heterocycles as selective estrogen receptor modulators (SERMs)
    • For synthesis of the tetracyclic core structure, see (a) Kanojia, R. M.; Jain, N.; Xu, J.; Sui, Z. Preparation of tetracyclic heterocycles as selective estrogen receptor modulators (SERMs). Tetrahedron Lett. 2004, 45, 5837-5839.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 5837-5839
    • Kanojia, R.M.1    Jain, N.2    Xu, J.3    Sui, Z.4
  • 21
    • 28644446613 scopus 로고    scopus 로고
    • A novel approach to the synthesis of 11,11-diinethyl-bisbenzopyran-5-ones
    • (b) Jain, N.; Xu, J.; Chen, N.; Sui, Z. A novel approach to the synthesis of 11,11-diinethyl-bisbenzopyran-5-ones. Tetrahedron Lett. 2006, 47, 225-228.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 225-228
    • Jain, N.1    Xu, J.2    Chen, N.3    Sui, Z.4
  • 22
    • 33744804499 scopus 로고    scopus 로고
    • note
    • (a) The absolute configuration of 1-(R) and 1-(S) has been determined by VCD spectroscopy data.
  • 23
    • 33744802570 scopus 로고    scopus 로고
    • note
    • (b) ee values were > 95; optical purities were determined by chiral Pak AD column.
  • 24
    • 0033571579 scopus 로고    scopus 로고
    • An ultrahigh-throughput screening assay for estrogen receptor ligands
    • Allan, G. F.; Hutchins, A.; Clancy, J. An ultrahigh-throughput screening assay for estrogen receptor ligands. Anal. Biochem. 1999, 275, 243-247.
    • (1999) Anal. Biochem. , vol.275 , pp. 243-247
    • Allan, G.F.1    Hutchins, A.2    Clancy, J.3
  • 25
    • 0037090988 scopus 로고    scopus 로고
    • Characterization of selective estrogen receptor modulator (SERM) activity in two triarylethylene oxybutyric acids
    • (b) Rufbin, V. N.; Ruenitz, P. C.; Boyd, J. L.; Boudinot, F. D.; Wiese, T. E. Characterization of Selective Estrogen Receptor Modulator (SERM) Activity in Two Triarylethylene Oxybutyric Acids. Biochem. Pharmacol. 2002, 63, 1517-1525.
    • (2002) Biochem. Pharmacol. , vol.63 , pp. 1517-1525
    • Rufbin, V.N.1    Ruenitz, P.C.2    Boyd, J.L.3    Boudinot, F.D.4    Wiese, T.E.5
  • 26
    • 0029947174 scopus 로고    scopus 로고
    • Molecular effects of genistein on estrogen receptor mediated pathways
    • Wang, T. T.; Sathyamoorthy, N.; Phang, J. M. Molecular Effects of Genistein on Estrogen Receptor Mediated Pathways. Carcinogenesis 1996, 17, 271-275.
    • (1996) Carcinogenesis , vol.17 , pp. 271-275
    • Wang, T.T.1    Sathyamoorthy, N.2    Phang, J.M.3
  • 27
    • 33744803126 scopus 로고    scopus 로고
    • note
    • Possible path way for auto oxidation is described in ref 8b.
  • 28
    • 0022547861 scopus 로고
    • Estrogen regulation of protein synthesis in the immature rat uterus: The analysis of proteins released into the medium during in vitro incubation
    • (a) Komm B. S.; Rusling D. J.; Lyttle C. R. Estrogen regulation of protein synthesis in the immature rat uterus: the analysis of proteins released into the medium during in vitro incubation. Endocrinology 1986, 118, 2411-2416.
    • (1986) Endocrinology , vol.118 , pp. 2411-2416
    • Komm, B.S.1    Rusling, D.J.2    Lyttle, C.R.3
  • 29
    • 23844531615 scopus 로고    scopus 로고
    • Bazedoxifene acetate: A selective estrogen receptor modulator with improved selectivity
    • (b) Komm, B. S.; Kharode, Y. P.; Bodine, P. V. N.; Harris, H. A.; Miller, C. P.; Lyttle, C. R. Bazedoxifene acetate: a selective estrogen receptor modulator with improved selectivity. Endocrinology 2005, 146 (9), 3999-4008.
    • (2005) Endocrinology , vol.146 , Issue.9 , pp. 3999-4008
    • Komm, B.S.1    Kharode, Y.P.2    Bodine, P.V.N.3    Harris, H.A.4    Miller, C.P.5    Lyttle, C.R.6
  • 30
    • 0035686794 scopus 로고    scopus 로고
    • Developing a SERM: Stringent preclinical selection criteria leading to an acceptable candidate (WAY-140424) for clinical evaluation
    • (a) Komm, B. S.; Lyttle, C. R. Developing a SERM: Stringent preclinical selection criteria leading to an acceptable candidate (WAY-140424) for clinical evaluation. Ann. N.Y. Acad. Sci. 2001, 949, 317-326.
    • (2001) Ann. N.Y. Acad. Sci. , vol.949 , pp. 317-326
    • Komm, B.S.1    Lyttle, C.R.2
  • 31
    • 0031171316 scopus 로고    scopus 로고
    • Activity of raloxifene in immature and ovariectomized rat uterotrophic assays
    • (b) Ashby J.; Odum, J.; Foster, J. R. Activity of raloxifene in immature and ovariectomized rat uterotrophic assays. Toxicol Pharmacol 1997, 25, 226-231.
    • (1997) Toxicol Pharmacol , vol.25 , pp. 226-231
    • Ashby, J.1    Odum, J.2    Foster, J.R.3
  • 32
    • 17744368482 scopus 로고    scopus 로고
    • Selective estrogenic effects of a novel triphenylethylene compound, FC1271a, on bone, cholesterol level, and reproductive tissues in intact and ovariectomized rats
    • (c) Qu, Q.; Zheng, H.; Dahllund, J.; Laine, A.; Cockcroft, N.; Peng, Z.; Koskinen, M.; Hemminki, K.; Kangas, L.; Väänänen, K.; Härkönen, P. Selective estrogenic effects of a novel triphenylethylene compound, FC1271a, on bone, cholesterol level, and reproductive tissues in intact and ovariectomized rats. Endocrinology 2000, 141, 809-820.
    • (2000) Endocrinology , vol.141 , pp. 809-820
    • Qu, Q.1    Zheng, H.2    Dahllund, J.3    Laine, A.4    Cockcroft, N.5    Peng, Z.6    Koskinen, M.7    Hemminki, K.8    Kangas, L.9    Väänänen, K.10    Härkönen, P.11
  • 33
    • 0032462194 scopus 로고    scopus 로고
    • U. J. LY353381.HCl: A novel raloxifene analogue with improved SERM potency and efficacy in vivo
    • (d) Sato, M.; Turner, C. H.; Wang, T.; Adrian, M. D.; Rowley, E.; Bryant, H. U. J. LY353381.HCl: a novel raloxifene analogue with improved SERM potency and efficacy in vivo. Pharmacol. Exp. Ther. 1998, 287, 1-7.
    • (1998) Pharmacol. Exp. Ther. , vol.287 , pp. 1-7
    • Sato, M.1    Turner, C.H.2    Wang, T.3    Adrian, M.D.4    Rowley, E.5    Bryant, H.6
  • 35
    • 0020530703 scopus 로고
    • Chronic hyperprolactinemia reduces peripheral beta-adrenergic responsiveness in male rats
    • (a) Simpkins, J. W.; Katovich, M. J.; Song, I.-C. Chronic hyperprolactinemia reduces peripheral beta-adrenergic responsiveness in male rats. Life Sci. 1983, 32, 1957-1966.
    • (1983) Life Sci. , vol.32 , pp. 1957-1966
    • Simpkins, J.W.1    Katovich, M.J.2    Song, I.-C.3
  • 36
    • 0022602272 scopus 로고
    • Regional skin temperature changes in a rat model for the menopausal hot flush
    • (b) Katovich, M. J.; Simpkins, J. W.; Berglund, L. A.; O'Meara, J. Regional skin temperature changes in a rat model for the menopausal hot flush. Maturitas 1986, 8, 67-76.
    • (1986) Maturitas , vol.8 , pp. 67-76
    • Katovich, M.J.1    Simpkins, J.W.2    Berglund, L.A.3    O'Meara, J.4
  • 38
    • 33744824306 scopus 로고    scopus 로고
    • note
    • Both 1-(R) and 1-(S) have similar pharmacokinetic properties in rats. The active metabolites 2d-(R) and 2d-(S) were detected in plasma predominantly with similar exposures as compared to the parent compounds 1-(R) and 1-(S), respectively. The total bioavailability calculated for 1-(R) and 1-(S) was about 11% and 9%, respectively. The partial hydrolyzed products were not detected in rat plasma.
  • 39
    • 33744824865 scopus 로고    scopus 로고
    • note
    • (a) The concentration of these compounds in blood was not determined in the immature uterotropic assays.
  • 40
    • 33744821574 scopus 로고    scopus 로고
    • note
    • (b) From our PK study, we have shown that 1-(R) and 1-(S) are extensively metabolized to 2d-(R) and 2d-(S), respectively. To correct the molecular weight change, a 1.4 mg/kg dose was chosen as standard screening dose.
  • 41
    • 33744822405 scopus 로고    scopus 로고
    • Selective estrogen receptor modulators
    • Matsumoto, T.; Morii, H.; Yazaki, Y.; Ouchi, Y., Eds.
    • (a) Matsumoto, T.; Morii, H.; Yazaki, Y.; Ouchi, Y., Eds. Selective Estrogen Receptor Modulators. Clin. Calcium 2002, 12 (12), 102 pp.
    • (2002) Clin. Calcium , vol.12 , Issue.12 , pp. 102
  • 42
    • 0030071445 scopus 로고    scopus 로고
    • Tripartite steroid hormone receptor pharmacology: Interaction with multiple effector sites as a basis for the cell- and promoter-specific action of these hormones
    • (b) For a detailed description of the current understanding of tissue-specific steroid hormone activities, see Katzenellenbogen, J. A.; O'Malley, B. W.; Katzenellenbogen, B. S. Tripartite steroid hormone receptor pharmacology: Interaction with multiple effector sites as a basis for the cell- and promoter-specific action of these hormones. Mol. Endocrinol. 1996, 10, 119-131.
    • (1996) Mol. Endocrinol. , vol.10 , pp. 119-131
    • Katzenellenbogen, J.A.1    O'Malley, B.W.2    Katzenellenbogen, B.S.3
  • 43
    • 33744798968 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.