메뉴 건너뛰기




Volumn 39, Issue 13, 1996, Pages 2482-2491

Chiral pyrrolo[2,3-d]pyrimidine and pyrimido[4,5-b]indole derivatives: Structure-activity relationships of potent, highly stereoselective A1-adenosine receptor antagonists

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINO 5,6 DIMETHYL 2 (3 CHLOROPHENYL) 7H PYRROLO[2,3 D]PYRIMIDINE; ADENINE DERIVATIVE; ADENOSINE A1 RECEPTOR ANTAGONIST; HYPOXANTHINE DERIVATIVE; INDOLE DERIVATIVE; N (1 PHENYLETHYL) 4 AMINO 5,6 DIMETHYL 2 PHENYL 7H PYRROLO[2,3 D]PYRIMIDINE; PYRIMIDINE DERIVATIVE; PYRIMIDO[4,5 B]INDOLE DERIVATIVE; PYRROLO[2,3 D]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0029896075     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960011w     Document Type: Article
Times cited : (46)

References (50)
  • 2
    • 0027661421 scopus 로고
    • Signal transduction via P2-purinergic receptors for extracellular ATP and other nucleotides
    • (a) Dubyak, G. R.; El-Moatassim, C. Signal transduction via P2-purinergic receptors for extracellular ATP and other nucleotides. Am. J. Physiol. 1993, 265, C577-C606.
    • (1993) Am. J. Physiol. , vol.265
    • Dubyak, G.R.1    El-Moatassim, C.2
  • 3
    • 0028277941 scopus 로고
    • Identification of a Uridine Nucleotide-selective G-protein-linked Receptor That Activates Phospholipase C
    • (b) Lazarowski, E. R.; Harden, T. K. Identification of a Uridine Nucleotide-selective G-protein-linked Receptor That Activates Phospholipase C. J. Biol. Chem. 1994, 269, 11830-11836.
    • (1994) J. Biol. Chem. , vol.269 , pp. 11830-11836
    • Lazarowski, E.R.1    Harden, T.K.2
  • 4
    • 0024470467 scopus 로고
    • Involvement of pyrimidinoceptors in the regulation of cell function by uridine and by uracil nucleotides
    • (c) Seifert, R.; Schultz, G. Involvement of pyrimidinoceptors in the regulation of cell function by uridine and by uracil nucleotides. Trends Pharmacol. Sci. 1989, 10, 365-369.
    • (1989) Trends Pharmacol. Sci. , vol.10 , pp. 365-369
    • Seifert, R.1    Schultz, G.2
  • 5
    • 0027426937 scopus 로고
    • Adenosine receptors and their modulators
    • Müller, C. E.; Scior, T. Adenosine receptors and their modulators. Pharm. Acta Helv. 1993, 68, 77-111.
    • (1993) Pharm. Acta Helv. , vol.68 , pp. 77-111
    • Müller, C.E.1    Scior, T.2
  • 7
    • 0028169223 scopus 로고
    • Cloned adenosine A3 receptors: Pharmacological properties, species differences and receptor function
    • Linden, J. Cloned adenosine A3 receptors: pharmacological properties, species differences and receptor function. Trends Pharmacol. Sci. 1994, 15, 298-306.
    • (1994) Trends Pharmacol. Sci. , vol.15 , pp. 298-306
    • Linden, J.1
  • 13
    • 0027420881 scopus 로고
    • Synthesis of paraxanthine analogs (1,7-disubstituted xanthines) and other xanthines unsubstituted at the 3-position: Structure-activity relationships at adenosine receptors
    • (a) Müller, C. E.; Shi, D.; Manning, M., Jr.; Daly, J. W. Synthesis of paraxanthine analogs (1,7-disubstituted xanthines) and other xanthines unsubstituted at the 3-position: structure-activity relationships at adenosine receptors. J. Med. Chem. 1993, 36, 3341-3349.
    • (1993) J. Med. Chem. , vol.36 , pp. 3341-3349
    • Müller, C.E.1    Shi, D.2    Manning Jr., M.3    Daly, J.W.4
  • 16
    • 0029009599 scopus 로고
    • Tricyclic theophylline derivatives with high water solubility: Structure-activity relationships at adenosine receptors, phosphodiesterases, and benzodiazepine binding sites
    • (d) Geis, U.; Grahner, B.; Pawlowski, M.; Drabczynska, A.; Gorczyca, M.; Müller, C. E. Tricyclic theophylline derivatives with high water solubility: structure-activity relationships at adenosine receptors, phosphodiesterases, and benzodiazepine binding sites. Pharmazie 1995, 50, 333-336.
    • (1995) Pharmazie , vol.50 , pp. 333-336
    • Geis, U.1    Grahner, B.2    Pawlowski, M.3    Drabczynska, A.4    Gorczyca, M.5    Müller, C.E.6
  • 18
    • 0027097122 scopus 로고
    • Adenosine A1 antagonists; A new therapeutic approach to cognitive deficits and acute renal failure
    • (b) Suzuki, F. Adenosine A1 antagonists; A new therapeutic approach to cognitive deficits and acute renal failure. Drug News Perspect. 1992, 5, 587-591.
    • (1992) Drug News Perspect. , vol.5 , pp. 587-591
    • Suzuki, F.1
  • 20
    • 0023680323 scopus 로고
    • 7-Deaza-9-phenyladenines a New Class of Adenosine Receptor Antagonists
    • Daly, J. W.; Padgett, W. L.; Eger, K. 7-Deaza-9-phenyladenines a New Class of Adenosine Receptor Antagonists. Biochem. Pharmacol. 1988, 37, 3749-3753.
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 3749-3753
    • Daly, J.W.1    Padgett, W.L.2    Eger, K.3
  • 22
    • 0016612023 scopus 로고
    • Synthese von 2-Amino-3-cyano-pyrrolen
    • (a) Roth, H. J.; Eger, K. Synthese von 2-Amino-3-cyano-pyrrolen. (Synthesis of 2-amino-3-cyanopyrroles.) Arch. Pharm. (Weinheim, Ger.) 1975, 308, 179-185.
    • (1975) Arch. Pharm. (Weinheim, Ger.) , vol.308 , pp. 179-185
    • Roth, H.J.1    Eger, K.2
  • 23
    • 0016799296 scopus 로고
    • Synthese von Pyrrolo[2,3-d]pyrimidinen
    • (b) Roth, H. J.; Eger, K. Synthese von Pyrrolo[2,3-d]pyrimidinen. (Synthesis of pyrrolo[2,3-d]pyrimidines.) Arch. Pharm. (Weinheim, Ger.) 1975, 308, 252-258.
    • (1975) Arch. Pharm. (Weinheim, Ger.) , vol.308 , pp. 252-258
    • Roth, H.J.1    Eger, K.2
  • 24
    • 84985264907 scopus 로고
    • Synthese von 7-unsubstituierten 7H-Pyrrolo[2,3-d]pyrimidinen
    • Pichler, H.; Folkers, G.; Roth, H. J.; Eger, K. Synthese von 7-unsubstituierten 7H-Pyrrolo[2,3-d]pyrimidinen. (Synthesis of 7-unsubstituted 7H-pyrrolo[2,3-d]pyrimidines.) Liebigs Ann. Chem. 1986, 1485-1505.
    • (1986) Liebigs Ann. Chem. , pp. 1485-1505
    • Pichler, H.1    Folkers, G.2    Roth, H.J.3    Eger, K.4
  • 25
    • 84986495375 scopus 로고
    • Selected reactions on the o-aminonitrile system of substituted pyrroles
    • Eger, K.; Pfahl, J. G.; Folkers, G.; Roth, H. J. Selected reactions on the o-aminonitrile system of substituted pyrroles. J. Heterocycl. Chem. 1987, 24, 425-430.
    • (1987) J. Heterocycl. Chem. , vol.24 , pp. 425-430
    • Eger, K.1    Pfahl, J.G.2    Folkers, G.3    Roth, H.J.4
  • 26
    • 69249187641 scopus 로고
    • Synthesis of Substituted Indoles and Pyrimido[4,5-b]indoles by Dehydrogenation of Tetrahydroindoles and Tetrahydro-pyrimidoindoles
    • Eger, K.; Lanzner, W.; Rothenhäusler, K. Synthesis of Substituted Indoles and Pyrimido[4,5-b]indoles by Dehydrogenation of Tetrahydroindoles and Tetrahydro-pyrimidoindoles. Liebigs Ann. Chem. 1993, 465-470.
    • (1993) Liebigs Ann. Chem. , pp. 465-470
    • Eger, K.1    Lanzner, W.2    Rothenhäusler, K.3
  • 27
    • 84986429632 scopus 로고
    • Phosphorus Pentoxide in Organic Synthesis; XI. A New Synthetic Approach to 7-Deazahypoxanthines
    • Girgis, N. S.; Jörgensen, A.; Pedersen, E. B. Phosphorus Pentoxide in Organic Synthesis; XI. A New Synthetic Approach to 7-Deazahypoxanthines. Synthesis 1985, 101-104.
    • (1985) Synthesis , pp. 101-104
    • Girgis, N.S.1    Jörgensen, A.2    Pedersen, E.B.3
  • 28
    • 0007710567 scopus 로고
    • 6,9-Disubstituted adenines: Effect on affinity for adenosine receptors of a chiral center in the 9-substituent
    • 6,9-Disubstituted adenines: effect on affinity for adenosine receptors of a chiral center in the 9-substituent. Med. Chem. Res. 1992, 2, 474.
    • (1992) Med. Chem. Res. , vol.2 , pp. 474
    • Thompson, R.D.1    Manning Jr., M.2    Daly, J.W.3    Olsson, R.A.4
  • 30
    • 0018831826 scopus 로고
    • Adenosine receptor activation in human fibroblasts: Nucleoside agonists and antagonists
    • Bruns, R. F. Adenosine receptor activation in human fibroblasts: nucleoside agonists and antagonists. Can. J. Physiol. Pharmacol. 1980, 58, 673-691.
    • (1980) Can. J. Physiol. Pharmacol. , vol.58 , pp. 673-691
    • Bruns, R.F.1
  • 31
    • 0025244943 scopus 로고
    • A novel synthesis of xanthines: Support for a new binding mode for xanthines with respect to adenosine at adenosine receptors
    • Peet, N. P.; Lentz, N. L.; Meng, E. C.; Dudley, M. W.; Ogden, A.-M. L.; Demeter, D. A.; Weintraub, H. J. R.; Bey, P. A novel synthesis of xanthines: support for a new binding mode for xanthines with respect to adenosine at adenosine receptors. J. Med. Chem. 1990, 33, 3127-3130.
    • (1990) J. Med. Chem. , vol.33 , pp. 3127-3130
    • Peet, N.P.1    Lentz, N.L.2    Meng, E.C.3    Dudley, M.W.4    Ogden, A.-M.L.5    Demeter, D.A.6    Weintraub, H.J.R.7    Bey, P.8
  • 32
    • 0026536910 scopus 로고
    • The three binding domain model of adenosine receptors: Molecular modeling aspects
    • Dooley, M. J.; Quinn, R. J. The three binding domain model of adenosine receptors: molecular modeling aspects. J. Med. Chem. 1992, 35, 211-216.
    • (1992) J. Med. Chem. , vol.35 , pp. 211-216
    • Dooley, M.J.1    Quinn, R.J.2
  • 34
    • 5244299704 scopus 로고
    • Pyrrolo[2,3-d]pyrimidines and pyrimido[4,5-b]indoles: Structure-activity relationships of potent adenosine receptor antagonists
    • Abstract
    • Müller, C. E.; Geis, U.; Grahner, B.; Lanzner, W.; Eger, K. Pyrrolo[2,3-d]pyrimidines and pyrimido[4,5-b]indoles: Structure-activity relationships of potent adenosine receptor antagonists. Drug Dev. Res. 1994, 31, 301 (Abstract).
    • (1994) Drug Dev. Res. , vol.31 , pp. 301
    • Müller, C.E.1    Geis, U.2    Grahner, B.3    Lanzner, W.4    Eger, K.5
  • 39
    • 0024449710 scopus 로고
    • Solubilities of adenosine antagonists determined by radioreceptor assay
    • Bruns, R. F.; Fergus, J. H. Solubilities of adenosine antagonists determined by radioreceptor assay. J. Pharm. Pharmacol. 1989, 41, 590-594.
    • (1989) J. Pharm. Pharmacol. , vol.41 , pp. 590-594
    • Bruns, R.F.1    Fergus, J.H.2
  • 40
    • 5244375382 scopus 로고
    • Solubility relationships among optically isomeric salts II. The camphorates of α para tolylethylamine
    • (a) Ingersoll, A. W.; Burns, F. B. Solubility relationships among optically isomeric salts II. The camphorates of α para tolylethylamine. J. Am. Chem. Soc. 1932, 54, 4712-4715.
    • (1932) J. Am. Chem. Soc. , vol.54 , pp. 4712-4715
    • Ingersoll, A.W.1    Burns, F.B.2
  • 41
    • 85171971723 scopus 로고
    • Die Konfiguration der Ephedrin-Basen
    • (b) Leithe, W. Die Konfiguration der Ephedrin-Basen. (The configuration of the ephedrine bases.) Chem. Ber. 1932, 65, 660-666.
    • (1932) Chem. Ber. , vol.65 , pp. 660-666
    • Leithe, W.1
  • 42
    • 5244360397 scopus 로고
    • Azione di Alcune Basi Otticamente Attive sugli Acidi Canfocarbonici Enantiomorfi: L'Inversione di Effetto cinetico
    • (c) Pratesi, P.; La Manna, A. Azione di Alcune Basi Otticamente Attive sugli Acidi Canfocarbonici Enantiomorfi: L'Inversione di Effetto cinetico. (Actions of Some Optically Active Bases on Enantiomeric Camphoric Acids: The Inversion of the Kinetic Effect.) Farmaco Ed. Sci. 1956, 11, 33-45.
    • (1956) Farmaco Ed. Sci. , vol.11 , pp. 33-45
    • Pratesi, P.1    La Manna, A.2
  • 45
    • 0022544512 scopus 로고
    • 3H]Xanthine amine congener of 1,3-dipropyl-8-phenylxanthine, an antagonist radioligand for adenosine receptors
    • 3H]Xanthine amine congener of 1,3-dipropyl-8-phenylxanthine, an antagonist radioligand for adenosine receptors. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 4089-4093.
    • (1986) Proc. Natl. Acad. Sci. U.S.A. , vol.83 , pp. 4089-4093
    • Jacobson, K.A.1    Ukena, D.2    Kirk, K.L.3    Daly, J.W.4
  • 49
    • 0021349111 scopus 로고
    • Molecular structures: Perception, autocorrelation descriptor and sar studies. System of atomic contributions for the calculation of the n-octanol/water partition coefficients
    • Broto, P.; Moreau, G.; Vandycke, C. Molecular structures: perception, autocorrelation descriptor and sar studies. System of atomic contributions for the calculation of the n-octanol/water partition coefficients. Eur. J. Med. Chem. 1984, 19, 71-78.
    • (1984) Eur. J. Med. Chem. , vol.19 , pp. 71-78
    • Broto, P.1    Moreau, G.2    Vandycke, C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.