메뉴 건너뛰기




Volumn 43, Issue 3, 2000, Pages 409-419

Syntheses and structure-activity relationships of 5,6,7,8-tetrahydro- 5,5,8,8-tetramethyl-2-quinoxaline derivatives with retinoic acid receptor α agonistic activity

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE; QUINOXALINE DERIVATIVE; RETINOIC ACID RECEPTOR;

EID: 0034628481     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990063w     Document Type: Article
Times cited : (43)

References (36)
  • 2
    • 0026742534 scopus 로고
    • Multiplicity generates diversity in the retinoic acid signaling pathways
    • Leid, M.; Kastner, P.; Chambon, P. Multiplicity Generates Diversity in the Retinoic Acid Signaling Pathways. Trends Biochem. Sci. 1992, 17, 427-433.
    • (1992) Trends Biochem. Sci. , vol.17 , pp. 427-433
    • Leid, M.1    Kastner, P.2    Chambon, P.3
  • 3
    • 0023193244 scopus 로고
    • The retinoids. A review of their clinical pharmacology and therapeutic use
    • (a) Orfanos, C. E.; Ehlert, R.; Gollnick, H. The Retinoids. A Review of Their Clinical Pharmacology and Therapeutic Use. Drugs 1987, 34, 459-503.
    • (1987) Drugs , vol.34 , pp. 459-503
    • Orfanos, C.E.1    Ehlert, R.2    Gollnick, H.3
  • 4
    • 0030887795 scopus 로고    scopus 로고
    • Current use and future potential role of retinoids in dermatology
    • (b) Orfanos, C. E.; Zouboulis, C. C.; Almond-Roesler, B.; Geilen, C. C. Current Use and Future Potential Role of Retinoids in Dermatology [Review]. Drugs 1997, 53, 358-388.
    • (1997) Drugs , vol.53 , pp. 358-388
    • Orfanos, C.E.1    Zouboulis, C.C.2    Almond-Roesler, B.3    Geilen, C.C.4
  • 7
  • 8
    • 0029796637 scopus 로고    scopus 로고
    • Retinoids in cancer chemoprevention
    • (d) Lotan, R. Retinoids in Cancer Chemoprevention. FASEB J. 1996, 10, 1031-1039.
    • (1996) FASEB J. , vol.10 , pp. 1031-1039
    • Lotan, R.1
  • 9
    • 0000147542 scopus 로고    scopus 로고
    • Recent advances in chemoprevention of cancer
    • (e) Hong, W. K.; Sporn, M. B. Recent Advances in Chemoprevention of Cancer. Science 1997, 278, 1073-1077.
    • (1997) Science , vol.278 , pp. 1073-1077
    • Hong, W.K.1    Sporn, M.B.2
  • 12
  • 13
    • 0025237258 scopus 로고
    • Structure-activity relationships of retinoids in developmental toxicology IV. Planar cisoid conformational restriction
    • (d) Willhite, C. C.; Dawson, M. I. Structure-Activity Relationships of Retinoids in Developmental Toxicology IV. Planar Cisoid Conformational Restriction. Toxicol. Appl. Pharmacol. 1990, 103, 324-344.
    • (1990) Toxicol. Appl. Pharmacol. , vol.103 , pp. 324-344
    • Willhite, C.C.1    Dawson, M.I.2
  • 14
    • 0023709173 scopus 로고
    • Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity
    • (a) Kagechika, H.; Kawachi, E.; Hashimoto, Y.; Himi, T.; Shudo, K. Retinobenzoic Acids. 1. Structure-Activity Relationships of Aromatic Amides with Retinoidal Activity. J. Med. Chem. 1988, 31, 2182-2192.
    • (1988) J. Med. Chem. , vol.31 , pp. 2182-2192
    • Kagechika, H.1    Kawachi, E.2    Hashimoto, Y.3    Himi, T.4    Shudo, K.5
  • 15
    • 0029761652 scopus 로고    scopus 로고
    • Identification of a retinoic acid receptor a subtype specific agonist
    • (b) Teng, M.; Duong, T. T.; Klein, E. S.; Chandraratna, R. A. S. Identification of a Retinoic Acid Receptor a Subtype Specific Agonist. J. Med. Chem. 1996, 39, 3035-3038.
    • (1996) J. Med. Chem. , vol.39 , pp. 3035-3038
    • Teng, M.1    Duong, T.T.2    Klein, E.S.3    Chandraratna, R.A.S.4
  • 16
    • 5544263313 scopus 로고    scopus 로고
    • Identification of retinoic acid receptor β subtype specific agonists
    • (c) Johnson, A. T.; Klein, E. S.; Wang, L.; Pino, M. E.; Chandraratna, R. A. S. Identification of Retinoic Acid Receptor β Subtype Specific Agonists. J. Med. Chem. 1996, 39, 5027-5030.
    • (1996) J. Med. Chem. , vol.39 , pp. 5027-5030
    • Johnson, A.T.1    Klein, E.S.2    Wang, L.3    Pino, M.E.4    Chandraratna, R.A.S.5
  • 19
    • 0029562846 scopus 로고
    • Synthesis, structure-activity relationships, and biological activities of ligands binding to retinoic acid receptor subtypes
    • (f) Charpentier, B.; Bernardon, J.-M.; Eustache, J.; Millois, C.; Martin, B.; Michel, S.; Shroot, B. Synthesis, Structure-Activity Relationships, and Biological Activities of Ligands Binding to Retinoic Acid Receptor Subtypes. J. Med. Chem. 1995, 38, 4993-5006.
    • (1995) J. Med. Chem. , vol.38 , pp. 4993-5006
    • Charpentier, B.1    Bernardon, J.-M.2    Eustache, J.3    Millois, C.4    Martin, B.5    Michel, S.6    Shroot, B.7
  • 24
    • 0001202818 scopus 로고
    • Efficacy of Am-80 ointment on psoriasis -A bilateral-paired comparative study with betamethasone valerate ointment (phase III study)-
    • (b) Ishibashi, Y. Efficacy of Am-80 Ointment on Psoriasis -A Bilateral-paired Comparative Study with Betamethasone Valerate Ointment (Phase III Study)-. Rinshouiyaku 1995, 11, 733-759.
    • (1995) Rinshouiyaku , vol.11 , pp. 733-759
    • Ishibashi, Y.1
  • 25
    • 0030052170 scopus 로고    scopus 로고
    • Novel synthetic retinoic acid inhibits rat collagen arthritis and differentially affects serum immunoglobulin subclass levels
    • Kuwabara, K.; Shudo, K.; Hori, Y. Novel Synthetic Retinoic Acid Inhibits Rat Collagen Arthritis and Differentially Affects Serum Immunoglobulin Subclass Levels. FEBS Lett. 1996, 378, 153-156.
    • (1996) FEBS Lett. , vol.378 , pp. 153-156
    • Kuwabara, K.1    Shudo, K.2    Hori, Y.3
  • 26
    • 0029133493 scopus 로고
    • A novel type of retinoic acid receptor antagonist: Synthesis and structure-activity relationships of heterocyclic ring-containing benzoic acid derivatives
    • (a) Yoshimura, H.; Nagai, M.; Hibi, S.; Kikuchi, K.; Abe, S.; Hida, T.; Higashi, S.; Hishinuma, I.; Yamanaka, T. A Novel Type of Retinoic Acid Receptor Antagonist: Synthesis and Structure-Activity Relationships of Heterocyclic Ring-Containing Benzoic Acid Derivatives. J. Med. Chem. 1995, 38, 3163-3173.
    • (1995) J. Med. Chem. , vol.38 , pp. 3163-3173
    • Yoshimura, H.1    Nagai, M.2    Hibi, S.3    Kikuchi, K.4    Abe, S.5    Hida, T.6    Higashi, S.7    Hishinuma, I.8    Yamanaka, T.9
  • 27
    • 0032514549 scopus 로고    scopus 로고
    • Syntheses and structure-activity relationships of novel retinoid X receptor agonists
    • (b) Hibi, S.; Kikuchi, K.; Yoshimura, H.; Nagai, M.; Tai, K.; Hida, T. Syntheses and Structure-Activity Relationships of Novel Retinoid X Receptor Agonists. J. Med. Chem. 1998, 41, 3245-3252.
    • (1998) J. Med. Chem. , vol.41 , pp. 3245-3252
    • Hibi, S.1    Kikuchi, K.2    Yoshimura, H.3    Nagai, M.4    Tai, K.5    Hida, T.6
  • 28
    • 0343572407 scopus 로고    scopus 로고
    • WO 97/02244
    • This compound was originally synthesized in our laboratory. A patent application was filed in June 1996 and opened in January 1997. Kikuchi, K.; Tagami, K.; Yoshimura, H.; Hibi, S.; Nagai, M.; Abe, S.; Okita, M.; Hida, T.; Higashi, S.; Tokuhara, N.; Kobayashi, S. Heterocyclic Carboxylic Acid Derivatives and Drugs Containing the Same. WO 97/02244. Recently Dr. P. Jones et al. reported a new route for the synthesis of ER-33635 and described the retinoidal activity of this compound. Jones, P.; Villeneuve, G. B.; Fei, C.; DeMarte, J.; Haggarty, A. J.; Nwe, K. T.; Martin, D. A.; Lebuis, A.-M.; Finkelstein, J. M.; Gour-Salin, B. J.; Chan, T. H.; Leyland-Jones, B. R. Synthesis and Structure-Activity Relationships of 2-Pyrazinylcarboxamidobenzoates and β-Ionylideneacetamidobenzoates with Retinoidal Activity. J. Med. Chem. 1998, 41, 3062-3077.
    • (1996) Heterocyclic Carboxylic Acid Derivatives and Drugs Containing the Same
    • Kikuchi, K.1    Tagami, K.2    Yoshimura, H.3    Hibi, S.4    Nagai, M.5    Abe, S.6    Okita, M.7    Hida, T.8    Higashi, S.9    Tokuhara, N.10    Kobayashi, S.11
  • 29
    • 0342702162 scopus 로고    scopus 로고
    • reported a new route for the synthesis of ER-33635 and described the retinoidal activity of this compound
    • This compound was originally synthesized in our laboratory. A patent application was filed in June 1996 and opened in January 1997. Kikuchi, K.; Tagami, K.; Yoshimura, H.; Hibi, S.; Nagai, M.; Abe, S.; Okita, M.; Hida, T.; Higashi, S.; Tokuhara, N.; Kobayashi, S. Heterocyclic Carboxylic Acid Derivatives and Drugs Containing the Same. WO 97/02244. Recently Dr. P. Jones et al. reported a new route for the synthesis of ER-33635 and described the retinoidal activity of this compound. Jones, P.; Villeneuve, G. B.; Fei, C.; DeMarte, J.; Haggarty, A. J.; Nwe, K. T.; Martin, D. A.; Lebuis, A.-M.; Finkelstein, J. M.; Gour-Salin, B. J.; Chan, T. H.; Leyland-Jones, B. R. Synthesis and Structure-Activity Relationships of 2-Pyrazinylcarboxamidobenzoates and β-Ionylideneacetamidobenzoates with Retinoidal Activity. J. Med. Chem. 1998, 41, 3062-3077.
    • Jones, P.1
  • 30
    • 15144358849 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships of 2-pyrazinylcarboxamidobenzoates and β-ionylideneacetamidobenzoates with retinoidal activity
    • This compound was originally synthesized in our laboratory. A patent application was filed in June 1996 and opened in January 1997. Kikuchi, K.; Tagami, K.; Yoshimura, H.; Hibi, S.; Nagai, M.; Abe, S.; Okita, M.; Hida, T.; Higashi, S.; Tokuhara, N.; Kobayashi, S. Heterocyclic Carboxylic Acid Derivatives and Drugs Containing the Same. WO 97/02244. Recently Dr. P. Jones et al. reported a new route for the synthesis of ER-33635 and described the retinoidal activity of this compound. Jones, P.; Villeneuve, G. B.; Fei, C.; DeMarte, J.; Haggarty, A. J.; Nwe, K. T.; Martin, D. A.; Lebuis, A.-M.; Finkelstein, J. M.; Gour-Salin, B. J.; Chan, T. H.; Leyland-Jones, B. R. Synthesis and Structure-Activity Relationships of 2-Pyrazinylcarboxamidobenzoates and β-Ionylideneacetamidobenzoates with Retinoidal Activity. J. Med. Chem. 1998, 41, 3062-3077.
    • (1998) J. Med. Chem. , vol.41 , pp. 3062-3077
    • Jones, P.1    Villeneuve, G.B.2    Fei, C.3    DeMarte, J.4    Haggarty, A.J.5    Nwe, K.T.6    Martin, D.A.7    Lebuis, A.-M.8    Finkelstein, J.M.9    Gour-Salin, B.J.10    Chan, T.H.11    Leyland-Jones, B.R.12
  • 32
    • 0001165143 scopus 로고    scopus 로고
    • The synthesis of o-Di-t-butyl heteroaromatic compounds
    • Groot, A. A.; Wynberg, H. The Synthesis of o-Di-t-butyl Heteroaromatic Compounds. J. Org. Chem. 1996, 31, 3954-3958.
    • (1996) J. Org. Chem. , vol.31 , pp. 3954-3958
    • Groot, A.A.1    Wynberg, H.2
  • 33
    • 84982417601 scopus 로고
    • Catalyzed addition of aldehydes to activated double bonds- A new synthetic approach
    • Steter, H. Catalyzed Addition of Aldehydes to Activated Double Bonds- A New Synthetic Approach, Angew. Chem., Int. Ed. Engl. 1976, 15, 639-647.
    • (1976) Angew. Chem., Int. Ed. Engl. , vol.15 , pp. 639-647
    • Steter, H.1
  • 36
    • 0029872796 scopus 로고    scopus 로고
    • Inhibitory effect of E3330, a novel quinone derivative able to suppress tumor necrosis factor-α generation, on activation of nuclear facter-κB
    • Goto, M.; Yamada, K.; Katayama, K.; Tanaka, I. Inhibitory Effect of E3330, a Novel Quinone Derivative able to Suppress Tumor Necrosis Factor-α Generation, on Activation of Nuclear Facter-κB. Mol. Pharmacol. 1996, 49, 860-873.
    • (1996) Mol. Pharmacol. , vol.49 , pp. 860-873
    • Goto, M.1    Yamada, K.2    Katayama, K.3    Tanaka, I.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.