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Volumn 40, Issue 26, 1997, Pages 4396-4405

Synthesis and structure-activity relationships of 3,7-dimethyl-1- propargylxanthine derivatives, A(2A)-selective adenosine receptor antagonists

Author keywords

[No Author keywords available]

Indexed keywords

3 PROPARGYL 5,6 DIAMINOURACIL; 3,7 DIMETHYL 1 PROPARGYLXANTHINE; 8 (3 CHLOROSTYRYL)CAFFEINE; 8 (3,4 DIMETHOXYSTYRYL) 7 METHYL 1,3 DIPROPYLXANTHINE; ADENOSINE A2 RECEPTOR; ADENOSINE RECEPTOR BLOCKING AGENT; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG; XANTHINE DERIVATIVE;

EID: 0031463493     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970515+     Document Type: Article
Times cited : (95)

References (57)
  • 1
    • 2842546966 scopus 로고    scopus 로고
    • Adenosine receptor antagonists: Structures and potential therapeutic applications
    • (a) Müller, C. E.; Stein, B. Adenosine receptor antagonists: structures and potential therapeutic applications. Curr. Pharm. Design 1996, 2, 501-530.
    • (1996) Curr. Pharm. Design , vol.2 , pp. 501-530
    • Müller, C.E.1    Stein, B.2
  • 2
    • 0031007914 scopus 로고    scopus 로고
    • 1-Adenosine receptor antagonists
    • 1-Adenosine receptor antagonists. Exp. Opin. Ther. Pat. 1997, 7, 419-440.
    • (1997) Exp. Opin. Ther. Pat. , vol.7 , pp. 419-440
    • Müller, C.E.1
  • 3
    • 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
  • 6
    • 0002328607 scopus 로고
    • Analogues of caffeine and theophylline: Activity as antagonists at adenosine receptors
    • Imai, S., Nakazawa, M., Eds.; Elsevier: Amsterdam
    • Daly, J. W. Analogues of caffeine and theophylline: activity as antagonists at adenosine receptors. In Role of adenosine and adenine nucleotides in the biological system; Imai, S., Nakazawa, M., Eds.; Elsevier: Amsterdam, 1991; pp 119-129.
    • (1991) Role of Adenosine and Adenine Nucleotides in the Biological System , pp. 119-129
    • Daly, J.W.1
  • 7
    • 0025925105 scopus 로고
    • 6,9-Disubstituted adenines: Potent, selective antagonists at the A1 adenosine receptor
    • 6,9-Disubstituted adenines: Potent, selective antagonists at the A1 adenosine receptor. J. Med. Chem. 1991, 34, 2877-2882.
    • (1991) J. Med. Chem. , vol.34 , pp. 2877-2882
    • Thompson, R.D.1    Secunda, S.2    Daly, J.W.3    Olsson, R.A.4
  • 8
    • 0030078102 scopus 로고    scopus 로고
    • 6-(5′-endohydroxy-endonorbomyl)-9-methyladenine (WRC-0571), a highly potent and selective, non-xanthine antagonist of A1 adenosine receptors
    • 6-(5′-endohydroxy-endonorbomyl)-9-methyladenine (WRC-0571), a highly potent and selective, non-xanthine antagonist of A1 adenosine receptors. J. Pharmacol. Exp. Ther. 1996, 276, 490-499.
    • (1996) J. Pharmacol. Exp. Ther. , vol.276 , pp. 490-499
    • Martin, P.L.1    Wysocki Jr., R.J.2    Barrett, R.J.3    May, J.M.4    Linden, J.5
  • 9
    • 0024989844 scopus 로고
    • 7-Deaza-2-phenyladenines: Structure-activity relationships of potent A1 selective adenosine receptor antagonists
    • (a) Müller, C. E.; Hide, I.; Daly, J. W.; Rothenhäusler, K.; Eger, K. 7-Deaza-2-phenyladenines: Structure-activity relationships of potent A1 selective adenosine receptor antagonists. J. Med. Chem. 1990, 33, 2822-2828.
    • (1990) J. Med. Chem. , vol.33 , pp. 2822-2828
    • Müller, C.E.1    Hide, I.2    Daly, J.W.3    Rothenhäusler, K.4    Eger, K.5
  • 10
    • 0029896075 scopus 로고    scopus 로고
    • Chiral pyrrolo[2,3-d]pyrimidine and pyrimido[4,5-b]indole derivatives: Structure-activity relationships of potent, highly stereoselective A1-adenosine receptor antagonists
    • (b) Müller, C. E.; Geis, U.; Grahner, B.; Lanzner, B.; Eger, K. Chiral pyrrolo[2,3-d]pyrimidine and pyrimido[4,5-b]indole derivatives: structure-activity relationships of potent, highly stereoselective A1-adenosine receptor antagonists. J. Med. Chem. 1996, 39, 2482-2491.
    • (1996) J. Med. Chem. , vol.39 , pp. 2482-2491
    • Müller, C.E.1    Geis, U.2    Grahner, B.3    Lanzner, B.4    Eger, K.5
  • 11
    • 0029947382 scopus 로고    scopus 로고
    • Pyrazolo[3,4-d]pyrimidines: C4, C6 substitution leads to adenosine A1 receptor selectivity
    • (a) Poulsen, S.-A.; Quinn, R. J. Pyrazolo[3,4-d]pyrimidines: C4, C6 substitution leads to adenosine A1 receptor selectivity. Bioorg. Med. Chem. Lett. 1996, 6, 357-360.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 357-360
    • Poulsen, S.-A.1    Quinn, R.J.2
  • 12
    • 0026641583 scopus 로고
    • Conformationally restrained, chiral (phenylisopropyl)amino-substituted pyrazolo[3,4-d]pyrimidines and purines with selectivity for adenosine A1 and A2 receptors
    • (b) Peet, N. P.; Lentz, N. L.; Sunder, S.; Dudley, M. W.; Ogden, A. M. L. Conformationally restrained, chiral (phenylisopropyl)amino-substituted pyrazolo[3,4-d]pyrimidines and purines with selectivity for adenosine A1 and A2 receptors. J. Med. Chem. 1992, 35, 3263-3269.
    • (1992) J. Med. Chem. , vol.35 , pp. 3263-3269
    • Peet, N.P.1    Lentz, N.L.2    Sunder, S.3    Dudley, M.W.4    Ogden, A.M.L.5
  • 13
    • 0025306964 scopus 로고
    • 4-Amino1,2,4triazolo[4,3-a]quinoxalines. A novel class of potent adenosine receptor antagonists and potential rapid-onset antidepressants
    • (a) Sarges, R.; Howard, H. R.; Browne, R. G.; Lebel, L. A.; Seymour, P. A.; Koe, B. K. 4-Amino[1,2,4)triazolo[4,3-a]quinoxalines. A novel class of potent adenosine receptor antagonists and potential rapid-onset antidepressants. J. Med. Chem. 1990, 33, 2240-2254.
    • (1990) J. Med. Chem. , vol.33 , pp. 2240-2254
    • Sarges, R.1    Howard, H.R.2    Browne, R.G.3    Lebel, L.A.4    Seymour, P.A.5    Koe, B.K.6
  • 16
    • 0028289758 scopus 로고
    • The effect of theophylline on parkinsonian symptoms
    • (a) Mally, J.; Stone, T. W. The effect of theophylline on parkinsonian symptoms. J. Pharm. Pharmacol. 1994, 46, 515-517.
    • (1994) J. Pharm. Pharmacol. , vol.46 , pp. 515-517
    • Mally, J.1    Stone, T.W.2
  • 18
    • 0022544144 scopus 로고    scopus 로고
    • Analogues of caffeine and theophylline: Effect of structural alterations on affinity at adenosine receptors
    • Daly, J. W.; Padgett, W. L.; Shamim, M. T. Analogues of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors. J. Med. Chem. 1996, 29, 1305-1308.
    • (1996) J. Med. Chem. , vol.29 , pp. 1305-1308
    • Daly, J.W.1    Padgett, W.L.2    Shamim, M.T.3
  • 19
    • 0023794288 scopus 로고
    • 3,7-Dimethyl-1-propargylxanthine: A potent and selective in vivo antagonist of adenosine analogues
    • Seale, T. W.; Abla, K. A.; Shamim, M. T.; Carney, J. M.; Daly, J. W. 3,7-Dimethyl-1-propargylxanthine: a potent and selective in vivo antagonist of adenosine analogues. Life Sci. 1988, 43, 1671-1684.
    • (1988) Life Sci. , vol.43 , pp. 1671-1684
    • Seale, T.W.1    Abla, K.A.2    Shamim, M.T.3    Carney, J.M.4    Daly, J.W.5
  • 20
    • 0024323119 scopus 로고
    • Effects of 8-phenyl and 8-cycloalkyl substituents on activity of mono-, di-, and trisubstituted alkylxanthines with substituion at the 1-, 3-, and 7-positions
    • Shamim, M. T.; Ukena, D.; Padgett, W.; Daly, J. W. Effects of 8-phenyl and 8-cycloalkyl substituents on activity of mono-, di-, and trisubstituted alkylxanthines with substituion at the 1-, 3-, and 7-positions. J. Med. Chem. 1989, 32, 1231-1237.
    • (1989) J. Med. Chem. , vol.32 , pp. 1231-1237
    • Shamim, M.T.1    Ukena, D.2    Padgett, W.3    Daly, J.W.4
  • 21
    • 0026690401 scopus 로고
    • (E)-1,3-Dialkyl-7-methyl-8-(3,4,5-trimethoxystyryl)xanthines: Potent and selective adenosine A2 antagonists
    • Shimada, J.; Suzuki, F.; Nonaka, H.; Ishii, A.; Ichikawa, S. (E)-1,3-Dialkyl-7-methyl-8-(3,4,5-trimethoxystyryl)xanthines: potent and selective adenosine A2 antagonists. J. Med. Chem. 1992, 35, 2342-2345.
    • (1992) J. Med. Chem. , vol.35 , pp. 2342-2345
    • Shimada, J.1    Suzuki, F.2    Nonaka, H.3    Ishii, A.4    Ichikawa, S.5
  • 25
    • 0027179838 scopus 로고
    • Synthesis of imidazo[1,2-c]pyrazolo[4,3-e]pyrimidines, pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines and 1,2,4-triazolo[5,1-i]purines: New potent A2 receptor antagonists
    • (c) Gatta, F.; Del Giudice, M. R.; Borioni, A.; Borea, P. A.; Dionisotti, S.; Ongini, E. Synthesis of imidazo[1,2-c]pyrazolo[4,3-e]pyrimidines, pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines and 1,2,4-triazolo[5,1-i]purines: new potent A2 receptor antagonists. Eur. J. Med. Chem. 1993, 28, 569-576.
    • (1993) Eur. J. Med. Chem. , vol.28 , pp. 569-576
    • Gatta, F.1    Del Giudice, M.R.2    Borioni, A.3    Borea, P.A.4    Dionisotti, S.5    Ongini, E.6
  • 28
    • 0006226187 scopus 로고
    • Structure-activity relationships for adenosine antagonists
    • Jacobson, K. A., Daly, J. W., Manganiello, V., Eds.; Springer: New York
    • (a) Bruns, R. F. Structure-activity relationships for adenosine antagonists. In Purines in cellular signaling: targets for new drugs; Jacobson, K. A., Daly, J. W., Manganiello, V., Eds.; Springer: New York, 1990.
    • (1990) Purines in Cellular Signaling: Targets for New Drugs
    • Bruns, R.F.1
  • 30
    • 0028939029 scopus 로고
    • 2A adenosine binding activities of some 1-aryl-1,4-dihydro-3-methyl-[1]benzopyrano[2,3-c]pyrazol-4-ones, 1-aryl-4,9-dihydro-3-methyl-1H-pyrazolo[3,4-6]quinolin-4-ones, and 1-aryl-1H-imidazo[4,5-b]quinoxalines
    • 2A adenosine binding activities of some 1-aryl-1,4-dihydro-3-methyl-[1]benzopyrano[2,3-c]pyrazol-4-ones, 1-aryl-4,9-dihydro-3-methyl-1H-pyrazolo[3,4-6]quinolin-4-ones, and 1-aryl-1H-imidazo[4,5-b]quinoxalines. J. Med. Chem. 1995, 38, 1330-1336.
    • (1995) J. Med. Chem. , vol.38 , pp. 1330-1336
    • Catarzi, D.1    Cecchi, L.2    Colotta, V.3    Filacchioni, G.4    Martini, C.5    Tacchi, P.6    Lucacchini, A.7
  • 31
    • 0017640061 scopus 로고
    • Selective inhibition of cyclic nucleotide phosphodiesterases by analogues of 1-methyl-3-isobutylxanthine
    • Kramer, G. L.; Garst, J. E.; Mitchel, S. S.; Wells, J. N. Selective inhibition of cyclic nucleotide phosphodiesterases by analogues of 1-methyl-3-isobutylxanthine. Biochemistry 1977, 16, 3316-3321.
    • (1977) Biochemistry , vol.16 , pp. 3316-3321
    • Kramer, G.L.1    Garst, J.E.2    Mitchel, S.S.3    Wells, J.N.4
  • 32
    • 33947452031 scopus 로고
    • Synthesis of 1-mono- And 1,3-disubstituted 6-aminouracils. Diuretic activity
    • Papesch, V.; Schroeder, E. F. Synthesis of 1-mono- and 1,3-disubstituted 6-aminouracils. Diuretic activity. J. Org. Chem. 1951, 1879-1890.
    • (1951) J. Org. Chem. , pp. 1879-1890
    • Papesch, V.1    Schroeder, E.F.2
  • 33
    • 0027420881 scopus 로고
    • Synthesis of paraxanthine analogues (1,7-disubstituted xanthines) and other xanthines unsubstituted at the 3-position: Structure-activity relationships at adenosine receptors
    • Müller, C. E.; Shi, D.; Manning, M., Jr.; Daly, J. W. Synthesis of paraxanthine analogues (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
  • 34
    • 0028363237 scopus 로고
    • Formation of oxazolo[3,2-a]purinones from propynyluracils
    • Müller, C. E. Formation of oxazolo[3,2-a]purinones from propynyluracils. J. Org. Chem. 1994, 59, 1928-1929.
    • (1994) J. Org. Chem. , vol.59 , pp. 1928-1929
    • Müller, C.E.1
  • 35
    • 0027531507 scopus 로고
    • General synthesis and properties of 1-monosubstituted xanthines
    • Müller, C. E. General synthesis and properties of 1-monosubstituted xanthines. Synthesis 1993, 125-128.
    • (1993) Synthesis , pp. 125-128
    • Müller, C.E.1
  • 36
    • 0028841206 scopus 로고
    • A new versatile synthesis of xanthines with variable substituents in the 1-, 3-, 7-, and 8-positions
    • Müller, C. E.; Sandoval-Ramírez, J. A new versatile synthesis of xanthines with variable substituents in the 1-, 3-, 7-, and 8-positions. Synthesis 1995, 1295-1299.
    • (1995) Synthesis , pp. 1295-1299
    • Müller, C.E.1    Sandoval-Ramírez, J.2
  • 37
    • 84920332297 scopus 로고
    • Über die Einwirkung von Aldehyden auf Orthodiamine der Pyrimidinreihe. (On the reaction of aldehydes with orthodiamine derivatives of pyrimidines)
    • Traube, W.; Nithack, W. Über die Einwirkung von Aldehyden auf Orthodiamine der Pyrimidinreihe. (On the reaction of aldehydes with orthodiamine derivatives of pyrimidines). Chem. Ber. 1906, 39, 227-235.
    • (1906) Chem. Ber. , vol.39 , pp. 227-235
    • Traube, W.1    Nithack, W.2
  • 38
    • 0017355354 scopus 로고
    • Oxidative cyclization of 6-amino-5-benzylidene-amino-1,3-dimethyluracils with thionyl chloride. A convenient synthesis of 8-substituted theophyllines
    • Senga, K.; Shimizu, K.; Nishigaki, S. Oxidative cyclization of 6-amino-5-benzylidene-amino-1,3-dimethyluracils with thionyl chloride. A convenient synthesis of 8-substituted theophyllines. Chem. Pharm. Bull. 1977, 25, 495-497.
    • (1977) Chem. Pharm. Bull. , vol.25 , pp. 495-497
    • Senga, K.1    Shimizu, K.2    Nishigaki, S.3
  • 41
    • 0025833464 scopus 로고
    • Caffeine analogues: Structure-activity relationships at adenosine receptors
    • Daly, J. W.; Hide, I.; Müller, C. E.; Shamim, M. Caffeine analogues: structure-activity relationships at adenosine receptors. Pharmacology 1991, 42, 309-321.
    • (1991) Pharmacology , vol.42 , pp. 309-321
    • Daly, J.W.1    Hide, I.2    Müller, C.E.3    Shamim, M.4
  • 44
    • 0015809706 scopus 로고
    • Photo-induced isomerization of 8-(3,4,5-trimethoxystyryl)caffeine as possible route of drug decomposition
    • Philip, J.; Szulczewski, D. H. Photo-induced isomerization of 8-(3,4,5-trimethoxystyryl)caffeine as possible route of drug decomposition. J. Pharm. Sci. 1973, 62, 1885-1887.
    • (1973) J. Pharm. Sci. , vol.62 , pp. 1885-1887
    • Philip, J.1    Szulczewski, D.H.2
  • 45
    • 0027141973 scopus 로고
    • Photoisomerization of a potent and selective adenosine A2 antagonist, (E)-1,3-dipropyl-8-(3,4-dimethoxystyryl)-7-methylxanthine
    • Nonaka, Y.; Shimada, J.; Nonaka, H.; Koike, N.; Aoki, N.; Kobayashi, H.; Kase, H.; Yamaguchi, K.; Suzuki, F. Photoisomerization of a potent and selective adenosine A2 antagonist, (E)-1,3-dipropyl-8-(3,4-dimethoxystyryl)-7-methylxanthine. J. Med. Chem. 1993, 36, 3731-3733.
    • (1993) J. Med. Chem. , vol.36 , pp. 3731-3733
    • Nonaka, Y.1    Shimada, J.2    Nonaka, H.3    Koike, N.4    Aoki, N.5    Kobayashi, H.6    Kase, H.7    Yamaguchi, K.8    Suzuki, F.9
  • 46
    • 0028036427 scopus 로고
    • Structure-activity relationships of 1,3-dialkylxanthine derivatives at rat A3 adenosine receptors
    • Kim, H. O.; Ji, X.-d.; Melman, N.; Olah, M. E.; Stiles, G. L.; Jacobson, K. A. Structure-activity relationships of 1,3-dialkylxanthine derivatives at rat A3 adenosine receptors. J. Med. Chem. 1994, 37, 3373-3382.
    • (1994) J. Med. Chem. , vol.37 , pp. 3373-3382
    • Kim, H.O.1    Ji, X.-D.2    Melman, N.3    Olah, M.E.4    Stiles, G.L.5    Jacobson, K.A.6
  • 47
    • 0029670366 scopus 로고    scopus 로고
    • Adenosine A2b receptors mediate an increase in interleukin (IL)-6 mRNA and IL-6 protein synthesis in human astroglioma cells
    • Fiebich, B. L.; Biber, K.; Gyufko, K,; Berger, M.; Bauer, J.; van Calker, D. Adenosine A2b receptors mediate an increase in interleukin (IL)-6 mRNA and IL-6 protein synthesis in human astroglioma cells. J. Neurochem. 1996, 66, 1426-1431.
    • (1996) J. Neurochem. , vol.66 , pp. 1426-1431
    • Fiebich, B.L.1    Biber, K.2    Gyufko, K.3    Berger, M.4    Bauer, J.5    Van Calker, D.6
  • 50
    • 0025939086 scopus 로고
    • Methylxanthines block antigen-induced responses in RBL-2H3 cells independently of adenosine receptors or cyclic AMP: Evidence for inhibition of antigen binding to IgE
    • Ali, H.; Müller, C. E.; Daly, J. W.; Beaven, M. A. Methylxanthines block antigen-induced responses in RBL-2H3 cells independently of adenosine receptors or cyclic AMP: evidence for inhibition of antigen binding to IgE. J. Pharmacol. Exp. Ther. 1991, 258, 954-962.
    • (1991) J. Pharmacol. Exp. Ther. , vol.258 , pp. 954-962
    • Ali, H.1    Müller, C.E.2    Daly, J.W.3    Beaven, M.A.4
  • 57
    • 0021957234 scopus 로고
    • 1,3-Dialkyl-8-(p-sulfophenyl)xanthines: Potent water-soluble antagonists for Al- And A2-adensosine receptors
    • Daly, J. W.; Padgett, W.; Shamim, M. T.; Butts-Lamb, P.; Waters, J. 1,3-Dialkyl-8-(p-sulfophenyl)xanthines: potent water-soluble antagonists for Al- and A2-adensosine receptors. J. Med. Chem. 1985, 28, 487-492.
    • (1985) J. Med. Chem. , vol.28 , pp. 487-492
    • Daly, J.W.1    Padgett, W.2    Shamim, M.T.3    Butts-Lamb, P.4    Waters, J.5


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