메뉴 건너뛰기




Volumn 46, Issue 8, 2003, Pages 1449-1455

Synthesis and antiviral activity of novel erythrofuranosyl imidazo[1,2-α]pyridine C-nucleosides constructed via palladium coupling of iodoimidazo[1,2-α]pyridines and dihydrofuran

Author keywords

[No Author keywords available]

Indexed keywords

2,5,6 TRICHLORO 1 (BETA DEXTRO RIBOFURANOSYL)BENZIMIDAZOLE; C NUCLEOSIDE; IMIDAZO[1,2 A]PYRIDINE DERIVATIVE; OSMIUM TETRAOXIDE; UNCLASSIFIED DRUG;

EID: 0142133661     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020339r     Document Type: Article
Times cited : (152)

References (41)
  • 1
    • 0000457348 scopus 로고
    • The chemistry of C-nucleosides
    • Townsend, L. B., Ed.; Plenum Press: New York
    • Watanabe, K. A. The Chemistry of C-Nucleosides. Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, pp 421-535.
    • (1994) Chemistry of Nucleosides and Nucleotides , vol.3 , pp. 421-535
    • Watanabe, K.A.1
  • 2
    • 0022177192 scopus 로고
    • The chemistry and biochemistry of C-nucleosides and C-arylglycosides
    • Elsevier: Amsterdam; Chapter 1
    • Hacksell, U.; Daves, G. D., Jr. The Chemistry and Biochemistry of C-Nucleosides and C-Arylglycosides. Progress in Medicinal Chemistry; Elsevier: Amsterdam, 1985; Chapter 1, pp 1-65.
    • (1985) Progress in Medicinal Chemistry , pp. 1-65
    • Hacksell, U.1    Daves G.D., Jr.2
  • 3
    • 0023478634 scopus 로고
    • The occurrence of natural stable analogues: Implications for the design of therapeutic agents
    • Daves, G. D., Jr. The Occurrence of Natural Stable Analogues: Implications for the Design of Therapeutic Agents. Acta Pharm. Suec. 1987, 24, 275-288.
    • (1987) Acta Pharm. Suec. , vol.24 , pp. 275-288
    • Daves G.D., Jr.1
  • 4
    • 0014803750 scopus 로고
    • Benzimidazole nucleosides, nucleotides, and related derivatives
    • Townsend, L. B.; Revankar, G. R. Benzimidazole Nucleosides, Nucleotides, and Related Derivatives. Chem. Rev. 1970, 70, 389-438.
    • (1970) Chem. Rev. , vol.70 , pp. 389-438
    • Townsend, L.B.1    Revankar, G.R.2
  • 5
    • 84981856168 scopus 로고
    • The synthesis of 2-Chloro-1-(β-D-ribofuranosyl)benzimidazole and certain related derivatives
    • Revankar, G. R.; Townsend, L. B. The Synthesis of 2-Chloro-1-(β-D-ribofuranosyl)benzimidazole and Certain Related Derivatives. J. Heterocycl. Chem 1968, 5, 477-483.
    • (1968) J. Heterocycl. Chem. , vol.5 , pp. 477-483
    • Revankar, G.R.1    Townsend, L.B.2
  • 6
    • 0028853743 scopus 로고
    • Design, synthesis, and antiviral activity of certain 2,5,6-Trihalo-1-(β-D-ribofuranosyl)benzimidazoles
    • Townsend, L. B.; Devivar, R. V.; Turk, S. R.; Nassiri, M. R.; Drach, J. C. Design, Synthesis, and Antiviral Activity of Certain 2,5,6-Trihalo-1-(β-D-ribofuranosyl)benzimidazoles. J. Med. Chem. 1995, 38, 4098-4105.
    • (1995) J. Med. Chem. , vol.38 , pp. 4098-4105
    • Townsend, L.B.1    Devivar, R.V.2    Turk, S.R.3    Nassiri, M.R.4    Drach, J.C.5
  • 7
    • 0031052117 scopus 로고    scopus 로고
    • Synthesis and antiviral activity of certain 5′-modified analogues of 2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole
    • Gudmundsson, K. S.; Drach, J. C.; Wotring, L. L.; Townsend, L. B. Synthesis and Antiviral Activity of Certain 5′-Modified Analogues of 2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole. J. Med. Chem. 1997, 40, 785-793.
    • (1997) J. Med. Chem. , vol.40 , pp. 785-793
    • Gudmundsson, K.S.1    Drach, J.C.2    Wotring, L.L.3    Townsend, L.B.4
  • 8
    • 0031985103 scopus 로고    scopus 로고
    • Inhibition of human cytomegalovirus DNA maturation by a benzimidazole nucleoside is mediated through the UL89 gene product
    • Underwood, M. R.; Harvey, R. J.; Stanat, S. C.; Hemphill, M. L.; Miller, T.; Drach, J. C.; Townsend, L. B.; Biron, K. K. Inhibition of Human Cytomegalovirus DNA Maturation by a Benzimidazole Nucleoside is Mediated Through the UL89 Gene Product. J. Virol. 1998, 72, 717-725.
    • (1998) J. Virol. , vol.72 , pp. 717-725
    • Underwood, M.R.1    Harvey, R.J.2    Stanat, S.C.3    Hemphill, M.L.4    Miller, T.5    Drach, J.C.6    Townsend, L.B.7    Biron, K.K.8
  • 9
    • 0000093809 scopus 로고
    • The disposition in rats and monkeys of 2-Bromo-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (BDCRB) and its 2,5,6-Trichloro Congener (TCRB)
    • Good, S. S.; Owens, B. S.; Townsend, L. B.; Drach, J. C. The Disposition in Rats and Monkeys of 2-Bromo-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (BDCRB) and its 2,5,6-Trichloro Congener (TCRB). Antiviral Res. 1994, 25(S), 103.
    • (1994) Antiviral Res. , vol.25 , Issue.S , pp. 103
    • Good, S.S.1    Owens, B.S.2    Townsend, L.B.3    Drach, J.C.4
  • 10
    • 0029991945 scopus 로고    scopus 로고
    • The condensation of 2,6-Dichloroimidazo[1,2-a]pyridine with ribonolactone gives a novel Imidazo[1,2-a]pyridine C-nucleoside with an unexpected site of ribosylation
    • Gudmundsson, K. S.; Drach, J. C.; Townsend, L. B. The Condensation of 2,6-Dichloroimidazo[1,2-a]pyridine with Ribonolactone Gives a Novel Imidazo[1,2-a]pyridine C-Nucleoside with an Unexpected Site of Ribosylation. Tetrahedron Lett. 1996, 37, 2365-2368.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2365-2368
    • Gudmundsson, K.S.1    Drach, J.C.2    Townsend, L.B.3
  • 11
    • 0030922260 scopus 로고    scopus 로고
    • Synthesis of Imidazo[1,2-a]pyridine C-nucleosides with an unexpected site of ribosylation
    • Gudmundsson, K. S.; Drach, J. C.; Townsend, L. B. Synthesis of Imidazo[1,2-a]pyridine C-Nucleosides with an Unexpected Site of Ribosylation. J. Org. Chem. 1997, 62, 3453-3459.
    • (1997) J. Org. Chem. , vol.62 , pp. 3453-3459
    • Gudmundsson, K.S.1    Drach, J.C.2    Townsend, L.B.3
  • 13
    • 0003624033 scopus 로고
    • Coupling of aryl halides with alkenes
    • Heck, R. F., Ed.; Academic Press: New York
    • Heck, R. F. Coupling of Aryl Halides with Alkenes. Palladium Reagents in Organic Synthesis; Heck, R. F., Ed.; Academic Press: New York, 1985; pp 276-287.
    • (1985) Palladium Reagents in Organic Synthesis , pp. 276-287
    • Heck, R.F.1
  • 14
    • 33645896595 scopus 로고
    • Paladium-catalyzed vinylic hydrogen substitution reactions with aryl, benzyl, and styryl halides
    • Heck, R. F.; Nolley, J. P., Jr. Paladium-Catalyzed Vinylic Hydrogen Substitution Reactions with Aryl, Benzyl, and Styryl Halides. J. Org. Chem. 1972, 37, 2320-2322.
    • (1972) J. Org. Chem. , vol.37 , pp. 2320-2322
    • Heck, R.F.1    Nolley J.P., Jr.2
  • 15
    • 9644285669 scopus 로고
    • A convenient synthesis of acetylenes catalytic substitutions of acetylenic hydrogen with bromoalkanes, iodoarenes, and bromopyridines
    • Sonogashira, K.; Tohda, Y.; Hagirara, N. A Convenient Synthesis of Acetylenes: catalytic Substitutions of Acetylenic Hydrogen with Bromoalkanes, Iodoarenes, and Bromopyridines. Tetrahedron Lett. 1975, 4467-4470.
    • (1975) Tetrahedron Lett. , pp. 4467-4470
    • Sonogashira, K.1    Tohda, Y.2    Hagirara, N.3
  • 16
    • 0000811585 scopus 로고
    • C-glycoside synthesis by palladium-mediated glycal-aglycon coupling reactions
    • Daves, G. D., Jr. C-Glycoside Synthesis by Palladium-Mediated Glycal-Aglycon Coupling Reactions. Acc. Chem. Res. 1990, 23, 201-206.
    • (1990) Acc. Chem. Res. , vol.23 , pp. 201-206
    • Daves G.D., Jr.1
  • 18
    • 0028323434 scopus 로고
    • Synthesis of aryl C-glycosides
    • Jaramillo, C.; Knapp, S. Synthesis of Aryl C-Glycosides. Synthesis 1994, 1-20.
    • (1994) Synthesis , pp. 1-20
    • Jaramillo, C.1    Knapp, S.2
  • 19
    • 0026714006 scopus 로고
    • Recent developments in the synthesis of C-glycosides
    • Postema, M. H. D. Recent Developments in the Synthesis of C-Glycosides. Tetrahedron 1992, 48, 8545-8599.
    • (1992) Tetrahedron , vol.48 , pp. 8545-8599
    • Postema, M.H.D.1
  • 20
    • 0026742776 scopus 로고
    • Synthesis of 2′-Deoxypseudouridine, 2′-Deoxyformycin B, and 2′, 3′-Dideoxyformycin B by palladium-mediated glycal-aglycon coupling
    • Zhang, H.-C.; Daves, G. D., Jr. Synthesis of 2′-Deoxypseudouridine, 2′-Deoxyformycin B, and 2′, 3′-Dideoxyformycin B by Palladium-Mediated Glycal-Aglycon Coupling. J. Org. Chem. 1992, 57, 4690-4696.
    • (1992) J. Org. Chem. , vol.57 , pp. 4690-4696
    • Zhang, H.-C.1    Daves G.D., Jr.2
  • 21
    • 0028866817 scopus 로고
    • An efficient and stereospecific synthesis of novel pyrazine C-nucleosides
    • Chen, J. J.; Walker, J. A., II; Liu, W.; Wise, D. S.; Townsend, L. B. An Efficient and Stereospecific Synthesis of Novel Pyrazine C-Nucleosides. Tetrahedron Lett. 1995, 36, 8363-8366.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 8363-8366
    • Chen, J.J.1    Walker J.A. II2    Liu, W.3    Wise, D.S.4    Townsend, L.B.5
  • 22
    • 0000427767 scopus 로고
    • Facile synthesis of 2′-Deoxy-3′-Keto- and 2′-Deoxypseudouridine derivatives and analogues. Palladium(II)-mediated coupling reactions of furanoid glycals
    • Cheng, J. C.-Y.; Hacksell, U.; Daves, G. D., Jr. Facile Synthesis of 2′-Deoxy-3′-Keto- and 2′-Deoxypseudouridine Derivatives and Analogues. Palladium(II)-Mediated Coupling Reactions of Furanoid Glycals. J. Org. Chem. 1986, 51, 3093-3098.
    • (1986) J. Org. Chem. , vol.51 , pp. 3093-3098
    • Cheng, J.C.-Y.1    Hacksell, U.2    Daves G.D., Jr.3
  • 23
    • 0027173719 scopus 로고
    • Enantio- and diastereoisomers of 2,4-Dimethoxy-5-(2,3-dideoxy-5-O-tritylribofuranosyl)pyrimidine. 2′,3′-Dideoxy pyrimidine C-nucleosides by palladium-mediated glycal-aglycon coupling
    • Zhang, H.-C.; Daves, G. D., Jr. Enantio- and Diastereoisomers of 2,4-Dimethoxy-5-(2,3-dideoxy-5-O-tritylribofuranosyl)pyrimidine. 2′,3′-Dideoxy Pyrimidine C-Nucleosides by Palladium-Mediated Glycal-Aglycon Coupling. J. Org. Chem. 1993, 58, 2557-2560.
    • (1993) J. Org. Chem. , vol.58 , pp. 2557-2560
    • Zhang, H.-C.1    Daves G.D., Jr.2
  • 24
    • 0030925803 scopus 로고    scopus 로고
    • An improved synthesis of 2-Chlorinated Imidazo[1,2-α]pyridines and the application of this procedure for the synthesis of several polychlorinated Imidazo[1,2-α]pylidines
    • Gudmundsson, K. S.; Drach, J. C.; Townsend, L. B. An Improved Synthesis of 2-Chlorinated Imidazo[1,2-α]pyridines and the Application of this Procedure for the Synthesis of Several Polychlorinated Imidazo[1,2-α]pylidines. Synth. Commun. 1997, 27, 1763-1776.
    • (1997) Synth. Commun. , vol.27 , pp. 1763-1776
    • Gudmundsson, K.S.1    Drach, J.C.2    Townsend, L.B.3
  • 25
    • 0001025730 scopus 로고
    • New applications of palladium in organic syntheses
    • Heck, R. F. New Applications of Palladium in Organic Syntheses. Pure Appl. Chem. 1978, 50, 691-701.
    • (1978) Pure Appl. Chem. , vol.50 , pp. 691-701
    • Heck, R.F.1
  • 26
    • 0001127732 scopus 로고
    • A kinetic investigation of some electronic ligand effects in the heck reaction with allylic alcohols
    • Benhaddou, R.; Czerneski, S.; Ville, G.; Zegar, A. A Kinetic Investigation of Some Electronic and Ligand Effects in the Heck Reaction with Allylic Alcohols. Organometallics 1988, 7, 2435-2439.
    • (1988) Organometallics , vol.7 , pp. 2435-2439
    • Benhaddou, R.1    Czerneski, S.2    Ville, G.3    Zegar, A.4
  • 27
    • 0000131734 scopus 로고
    • Large rate accelerations in the stille reaction with tri-2-furylphosphine and triphenylarsine as palladium ligands: Mechanistic and synthetic implications
    • Farina, V.; Krishnan, B. Large Rate Accelerations in the Stille Reaction with Tri-2-furylphosphine and Triphenylarsine as Palladium Ligands: Mechanistic and Synthetic Implications. J. Am. Chem. Soc. 1991, 113, 9585-9595.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 9585-9595
    • Farina, V.1    Krishnan, B.2
  • 28
    • 0001366523 scopus 로고
    • Palladium-catalyzed arylation of unsaturated acetals and ketals
    • Zebovitz, T. C.; Heck, R. F. Palladium-Catalyzed Arylation of Unsaturated Acetals and Ketals. J. Org. Chem. 1977, 42, 3907-3909.
    • (1977) J. Org. Chem. , vol.42 , pp. 3907-3909
    • Zebovitz, T.C.1    Heck, R.F.2
  • 29
    • 0001541185 scopus 로고
    • The effect of added silver nitrate on the palladium-catalyzed arylation of allyltrimethylsilanes
    • Karabelas, K.; Westerlund, C.; Hallberg, A. The Effect of Added Silver Nitrate on the Palladium-Catalyzed Arylation of Allyltrimethylsilanes. J. Org. Chem. 1985, 50, 3896-3900.
    • (1985) J. Org. Chem. , vol.50 , pp. 3896-3900
    • Karabelas, K.1    Westerlund, C.2    Hallberg, A.3
  • 30
    • 0025190548 scopus 로고
    • Palladium-catalyzed synthesis of trans-2,5-Diaryltetrahydrofurans, potent platelet activating factor antagonists
    • Larock, R. C.; Gong, W. H. Palladium-Catalyzed Synthesis of trans-2,5-Diaryltetrahydrofurans, Potent Platelet Activating Factor Antagonists. J. Org. Chem. 1990, 55, 407-408.
    • (1990) J. Org. Chem. , vol.55 , pp. 407-408
    • Larock, R.C.1    Gong, W.H.2
  • 31
    • 0000155224 scopus 로고
    • Improved procedure for the palladium-catalyzed intermolecular arylation of cyclic alkenes
    • Larock, R. C.; Gong, W. H.; Baker, B. E. Improved Procedure for the Palladium-Catalyzed Intermolecular Arylation of Cyclic Alkenes. Tetrahedron Lett. 1989, 30, 2603-2606.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 2603-2606
    • Larock, R.C.1    Gong, W.H.2    Baker, B.E.3
  • 32
    • 0000554041 scopus 로고
    • Catalytic osmium tetroxide oxidation of olenfins: cis-1,2-Cyclohexanediol
    • Noland, W., Ed.; John Wiley and Sons: New York
    • VanRheenen, V.; Cha, D. Y.; Hartley, W. M. Catalytic Osmium Tetroxide Oxidation of Olenfins: cis-1,2-Cyclohexanediol. Organic Syntheses; Noland, W., Ed.; John Wiley and Sons: New York, 1988; Collective Vol. 6; pp 342-348.
    • (1988) Organic Syntheses , vol.6 , pp. 342-348
    • VanRheenen, V.1    Cha, D.Y.2    Hartley, W.M.3
  • 34
    • 0000183327 scopus 로고
    • Nuclear magnetic respnance spectroscopy in the study of nucleic acid components and certain related derivatives
    • Zorbach, W. W., Tipson, R. S., Eds.; Wiley-Interscience: New York
    • Townsend, L. B. Nuclear Magnetic Respnance Spectroscopy in the Study of Nucleic Acid Components and Certain Related Derivatives. Synthetic Procedures in Nucleic Acid Chemistry; Zorbach, W. W., Tipson, R. S., Eds.; Wiley-Interscience: New York, 1973; Vol. 2; pp 267-398.
    • (1973) Synthetic Procedures in Nucleic Acid Chemistry , vol.2 , pp. 267-398
    • Townsend, L.B.1
  • 35
    • 0000139675 scopus 로고
    • Synthesis of 5-Methyluridine and its 5′-Mercapto-, 2-Amino-, and 4′,5′-unsaturated analogues
    • Skaric, V.; Matulic-Adamic, J. Synthesis of 5-Methyluridine and Its 5′-Mercapto-, 2-Amino-, and 4′,5′-Unsaturated Analogues. Helv. Chim. Acta 1980, 63, 2179-2186.
    • (1980) Helv. Chim. Acta , vol.63 , pp. 2179-2186
    • Skaric, V.1    Matulic-Adamic, J.2
  • 37
    • 0017073707 scopus 로고
    • Anti-viral activity of arabinofuranosyladenine and arabinofuranosylhypoxanthine in herpes simplex virus-infected KB cells. Selective inhibition of viral DNA synthesis in synchronized suspension cultures
    • Shipman, C., Jr.; Smith, S. H.; Carlson, R. H.; Drach, J. C. Anti-viral Activity of Arabinofuranosyladenine and Arabinofuranosylhypoxanthine in Herpes Simplex Virus-Infected KB Cells. Selective Inhibition of Viral DNA Synthesis in Synchronized Suspension Cultures. Antimicrob. Agents Chemother. 1976, 9, 120-127.
    • (1976) Antimicrob. Agents Chemother. , vol.9 , pp. 120-127
    • Shipman C., Jr.1    Smith, S.H.2    Carlson, R.H.3    Drach, J.C.4
  • 39
    • 0025304011 scopus 로고
    • A mictotiter virus yield reduction assay for the evaluation of antiviral compounds against human cytomegalovirus and herpes simplex virus
    • Prichard, M. N.; Turk, S. R.; Coleman, L. A.; Engelhardt, S. L.; Shipman, C., Jr., Drach, J. C. A Mictotiter Virus Yield Reduction Assay for the Evaluation of Antiviral Compounds Against Human Cytomegalovirus and Herpes Simplex Virus. J. Virol. Methods 1990, 28, 101-106.
    • (1990) J. Virol. Methods , vol.28 , pp. 101-106
    • Prichard, M.N.1    Turk, S.R.2    Coleman, L.A.3    Engelhardt, S.L.4    Shipman C., Jr.5    Drach, J.C.6
  • 40
    • 0024993530 scopus 로고
    • A three-dimensional model to analyze drug-drug interactions
    • Prichard, M. N.; Shipman, C., Jr. A Three-Dimensional Model to Analyze Drug-Drug Interactions. Antiviral Res. 1990, 14, 181-206.
    • (1990) Antiviral Res. , vol.14 , pp. 181-206
    • Prichard, M.N.1    Shipman C., Jr.2
  • 41
    • 0025756141 scopus 로고
    • Three-dimensional analysis of the synergistic cytotoxicity of ganciclovir and zidovudine
    • Prichard, M. N.; Prichard, L. E.; Baguley, W. A.; Nassiri, M. R.; Shipman, C., Jr. Three-Dimensional Analysis of the Synergistic Cytotoxicity of Ganciclovir and Zidovudine. Antiviral Res. 1991, 35, 1060-1065.
    • (1991) Antiviral Res. , vol.35 , pp. 1060-1065
    • Prichard, M.N.1    Prichard, L.E.2    Baguley, W.A.3    Nassiri, M.R.4    Shipman C., Jr.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.