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Volumn 50, Issue 17, 2007, Pages 4105-4112

Synthesis and antiviral and cytostatic evaluations of the new c-5 substituted pyrimidine and furo[2,3-d]pyrimidine 4′,5′-didehydro-L- ascorbic acid derivatives

Author keywords

[No Author keywords available]

Indexed keywords

1 (6 BUTYLFURO[2,3 D]PYRIMIDIN 2 ON 3 YL) 2 (2',3' DI O BENZYL 2' BUTEN 4' OLIDYLIDENE)ETHANE; 1 (6 HEXYLFURO[2,3 D]PYRIMIDIN 2 ON 3 YL) 2 (2',3' DI O BENZYL 2' BUTEN 4' OLIDYLIDENE)ETHANE; 1 [5 (4 BROMOPHENYLETHYN 1'' YL)URACIL 1 YL] 2 (2',3' DI O BENZYL 2' BUTEN 4' OLIDYLIDENE)ETHANE; 1 [5 (4'' PHENYLBUT 1'' YN 1'' YL)URACIL 1 YL] 2 (2',3' DI O BENZYL 2' BUTEN 4' OLIDYLIDENE)ETHANE; 1 [6 (4 BROMOPHENYL)FURO[2,3 D]PYRIMIDIN 2 ON 3 YL] 2 (2',3' DI O BENZYL 2' BUTEN 4' OLIDYLIDENE)ETHANE; 5 (2 BROMOVINYL) 2' DEOXYURIDINE; ACICLOVIR; ALKYNE DERIVATIVE; ALKYNYL GROUP; ASCORBIC ACID DERIVATIVE; BICYCLO COMPOUND; CIDOFOVIR; GANCICLOVIR; IODINE DERIVATIVE; PHENYLACETYLENE; PYRIMIDINE DERIVATIVE; RIBAVIRIN; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

EID: 34548136091     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070324z     Document Type: Article
Times cited : (47)

References (39)
  • 1
    • 0345118256 scopus 로고    scopus 로고
    • The Protective Effect of Ascorbic Acid Derivative on PC12 Cells: Involvement of Its ROS Scavenging Ability
    • Du, C.-B.; Liu, J.-W.; Su, W.; Ren, Y.-H.; Wei, D.-Z. The Protective Effect of Ascorbic Acid Derivative on PC12 Cells: Involvement of Its ROS Scavenging Ability. Life Sci. 2003, 74, 771-780.
    • (2003) Life Sci , vol.74 , pp. 771-780
    • Du, C.-B.1    Liu, J.-W.2    Su, W.3    Ren, Y.-H.4    Wei, D.-Z.5
  • 2
    • 0028071728 scopus 로고
    • Chemistry of L-Ascorbic Acid: Regioselective and Stereocontrolled 2-C- and 3-C-Allylation via Thermal Claisen Rearrangement
    • Wimalasena, K.; Mahindaratne, M. P. D. Chemistry of L-Ascorbic Acid: Regioselective and Stereocontrolled 2-C- and 3-C-Allylation via Thermal Claisen Rearrangement. J. Org. Chem. 1994, 59, 3427-3432.
    • (1994) J. Org. Chem , vol.59 , pp. 3427-3432
    • Wimalasena, K.1    Mahindaratne, M.P.D.2
  • 4
    • 0023013510 scopus 로고
    • A New Class of Synthetic Biological Response Modifiers: The Methylfurylbutyrolactones (Nafocare)
    • Veltri, R. W.; Fodor, G.; Liu, C. M.; Woolverton, C. J.; Baseler, M. W. A New Class of Synthetic Biological Response Modifiers: The Methylfurylbutyrolactones (Nafocare). J. Biol. Res. Mod. 1986, 5, 444-461.
    • (1986) J. Biol. Res. Mod , vol.5 , pp. 444-461
    • Veltri, R.W.1    Fodor, G.2    Liu, C.M.3    Woolverton, C.J.4    Baseler, M.W.5
  • 5
    • 0022858979 scopus 로고
    • Stimulation of Human Pmn in Vitro by a Succinimide Molecular Complex of Methylfurylbutyrolactones
    • Woolverton, C. J.; Veltri, R. W.; Snyder, I. S. Stimulation of Human Pmn in Vitro by a Succinimide Molecular Complex of Methylfurylbutyrolactones. J. Biol. Res. Mod. 1986, 5, 527-538.
    • (1986) J. Biol. Res. Mod , vol.5 , pp. 527-538
    • Woolverton, C.J.1    Veltri, R.W.2    Snyder, I.S.3
  • 6
    • 0025879537 scopus 로고
    • 3-O-Alkylascorbic Acids as Free-Radical Quenchers: Synthesis and Inhibitory Effect on Lipid Peroxidation
    • Nihro, Y.; Miyataka, H.; Sudo, T.; Matsumoto, H.; Satoh, T. J. 3-O-Alkylascorbic Acids as Free-Radical Quenchers: Synthesis and Inhibitory Effect on Lipid Peroxidation. J. Med. Chem. 1991, 34, 2152-2157.
    • (1991) J. Med. Chem , vol.34 , pp. 2152-2157
    • Nihro, Y.1    Miyataka, H.2    Sudo, T.3    Matsumoto, H.4    Satoh, T.J.5
  • 7
    • 25144450579 scopus 로고    scopus 로고
    • Stannous Chloride Induces Alterations in Enzyme Activities, Lipid Peroxidation and Histopathology in Male Rabbit: Antioxidant Role of Vitamin C
    • El-Demerdash, F. M.; Yousef, M. I.; Zoheir, M. A. Stannous Chloride Induces Alterations in Enzyme Activities, Lipid Peroxidation and Histopathology in Male Rabbit: Antioxidant Role of Vitamin C. Food Chem. Toxicol. 2005, 43, 1743-1752.
    • (2005) Food Chem. Toxicol , vol.43 , pp. 1743-1752
    • El-Demerdash, F.M.1    Yousef, M.I.2    Zoheir, M.A.3
  • 8
    • 4544245974 scopus 로고    scopus 로고
    • Manfredini, S.; Vertuani, S.; Pavan, B.; Vitali, F.; Scaglianti, M.; Bartolotti, F.; Biondi, C.; Scatturin, A.; Prasad, P.; Dalpiaz, A. Design, Synthesis and in Vitro Evaluation on HRPE Cells of Ascorbic and 6-Bromoascorbic Acid Conjugates with Neuroactive Molecules. Bioorg. Med. Chem. 2004, 12, 5453-5463.
    • Manfredini, S.; Vertuani, S.; Pavan, B.; Vitali, F.; Scaglianti, M.; Bartolotti, F.; Biondi, C.; Scatturin, A.; Prasad, P.; Dalpiaz, A. Design, Synthesis and in Vitro Evaluation on HRPE Cells of Ascorbic and 6-Bromoascorbic Acid Conjugates with Neuroactive Molecules. Bioorg. Med. Chem. 2004, 12, 5453-5463.
  • 9
    • 0023279665 scopus 로고
    • Targets for the Antiviral Activity of Pyrimidine and Purine Analogs
    • De Clercq, E. Targets for the Antiviral Activity of Pyrimidine and Purine Analogs. Nucleosides Nucleotides 1987, 6, 197-207.
    • (1987) Nucleosides Nucleotides , vol.6 , pp. 197-207
    • De Clercq, E.1
  • 10
    • 0021280232 scopus 로고
    • Biochemical Aspects of the Selective Antiherpes Activity of Nucleoside Analogues
    • De Clercq, E. Biochemical Aspects of the Selective Antiherpes Activity of Nucleoside Analogues. Biochem. Pharmacol. 1984, 33, 2159-2169.
    • (1984) Biochem. Pharmacol , vol.33 , pp. 2159-2169
    • De Clercq, E.1
  • 11
    • 0000393677 scopus 로고    scopus 로고
    • De Clercq, E.; Descamps, J.; De Somer, P.; Barr, P. J.; Jones, A. S.; Walker, R. T. (E)-5-(2-Bromovinyl)-2′-deoxyuridine: A Potent and Selective Anti-Herpes Agent. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 2947-2951.
    • De Clercq, E.; Descamps, J.; De Somer, P.; Barr, P. J.; Jones, A. S.; Walker, R. T. (E)-5-(2-Bromovinyl)-2′-deoxyuridine: A Potent and Selective Anti-Herpes Agent. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 2947-2951.
  • 13
    • 0028260962 scopus 로고
    • 5-Substituted-2′-Deoxyuridines as Anti-HSV-1 Agents: Synthesis and Structure-Activity Relationship
    • Herdewijn, P. 5-Substituted-2′-Deoxyuridines as Anti-HSV-1 Agents: Synthesis and Structure-Activity Relationship. Antiviral Chem. Chemother. 1994, 5, 131-146.
    • (1994) Antiviral Chem. Chemother , vol.5 , pp. 131-146
    • Herdewijn, P.1
  • 15
    • 0022545923 scopus 로고
    • Synthesis and Antitumor and Activiral Properties of 5-Alkyl-2′- deoxyuridines, 3′,5′-Cyclic Monophosphates, and Neutral Cyclic Triesters
    • Beres, J.; Bentrude, W. G.; Balzarini, J.; De Clercq, E.; Otvos, L. Synthesis and Antitumor and Activiral Properties of 5-Alkyl-2′- deoxyuridines, 3′,5′-Cyclic Monophosphates, and Neutral Cyclic Triesters. J. Med. Chem. 1986, 29, 494-499.
    • (1986) J. Med. Chem , vol.29 , pp. 494-499
    • Beres, J.1    Bentrude, W.G.2    Balzarini, J.3    De Clercq, E.4    Otvos, L.5
  • 16
    • 0020529728 scopus 로고    scopus 로고
    • De Clercq, E.; Descamps, J.; Balzarini, J.; Giziewicz, J.; Barr, P. J.; Robins, M. J. Synthesis and Biological Activities of 5-Alkynyluracil Nucleosides. J. Med. Chem. 1983, 26, 661-666.
    • De Clercq, E.; Descamps, J.; Balzarini, J.; Giziewicz, J.; Barr, P. J.; Robins, M. J. Synthesis and Biological Activities of 5-Alkynyluracil Nucleosides. J. Med. Chem. 1983, 26, 661-666.
  • 19
    • 0034727849 scopus 로고    scopus 로고
    • Highly Potent and Selective Inhibition of Varicella-Zoster Virus (VZV) by Bicyclic Furo Pyrimidine Nucleosides Bearing an Aryl Side Chain
    • McGuigan, C.; Barucki, H.; Blewett, S.; Carangio, A.; Erichsen, J. T.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Highly Potent and Selective Inhibition of Varicella-Zoster Virus (VZV) by Bicyclic Furo Pyrimidine Nucleosides Bearing an Aryl Side Chain. J. Med. Chem. 2000, 43, 4993-4997.
    • (2000) J. Med. Chem , vol.43 , pp. 4993-4997
    • McGuigan, C.1    Barucki, H.2    Blewett, S.3    Carangio, A.4    Erichsen, J.T.5    Andrei, G.6    Snoeck, R.7    De Clercq, E.8    Balzarini, J.9
  • 21
    • 0037130292 scopus 로고    scopus 로고
    • Chemotherapy of Varicella-Zoster Virus by a Novel Class of Highly Specific Anti-VZV Bicyclic Pyrimidine Nucleosides
    • Balzarini, J.; McGuigan, C. Chemotherapy of Varicella-Zoster Virus by a Novel Class of Highly Specific Anti-VZV Bicyclic Pyrimidine Nucleosides. Biochim. Biophys. Acta 2002, 1587, 287-295.
    • (2002) Biochim. Biophys. Acta , vol.1587 , pp. 287-295
    • Balzarini, J.1    McGuigan, C.2
  • 24
    • 0034649613 scopus 로고    scopus 로고
    • Synthesis and Antitumor Activities of Novel Pyrimidine Derivatives of 2,3-O,O-Dibenzyl-6-deoxy-L-ascorbic Acid and 4,5-Didehydro-5,6-dideoxy-L-ascorbic Acid
    • Raić-Malić, S.; Svedružić, D.; Gazivoda, T.; Marunović, A.; Hergold-Brundić, A.; Nagl, A.; Balzarini, J.; De Clercq, E.; Mintas, M. Synthesis and Antitumor Activities of Novel Pyrimidine Derivatives of 2,3-O,O-Dibenzyl-6-deoxy-L-ascorbic Acid and 4,5-Didehydro-5,6-dideoxy-L-ascorbic Acid. J. Med. Chem. 2000, 43, 4806-4811.
    • (2000) J. Med. Chem , vol.43 , pp. 4806-4811
    • Raić-Malić, S.1    Svedružić, D.2    Gazivoda, T.3    Marunović, A.4    Hergold-Brundić, A.5    Nagl, A.6    Balzarini, J.7    De Clercq, E.8    Mintas, M.9
  • 25
    • 33845296975 scopus 로고    scopus 로고
    • The Novel C-5 Aryl, Alkenyl, and Alkynyl Substituted Uracil Derivatives of L-Ascorbic Acid: Synthesis, Cytostatic, and Antiviral Activity Evaluations
    • Gazivoda, T.; Raić-Malić, S.; Marjanović, M.; Kralj, M.; Pavelić, K.; Balzarini, J.; De Clercq, E.; Mintas, M. The Novel C-5 Aryl, Alkenyl, and Alkynyl Substituted Uracil Derivatives of L-Ascorbic Acid: Synthesis, Cytostatic, and Antiviral Activity Evaluations. Bioorg. Med. Chem. 2007, 15, 749-758.
    • (2007) Bioorg. Med. Chem , vol.15 , pp. 749-758
    • Gazivoda, T.1    Raić-Malić, S.2    Marjanović, M.3    Kralj, M.4    Pavelić, K.5    Balzarini, J.6    De Clercq, E.7    Mintas, M.8
  • 28
    • 0025283720 scopus 로고
    • Solvent, Not Palladium Oxidadon State, Is the Primary Determinant for Successful Coupling of Terminal Alkynes with Iodo-nucleosides
    • Robins, M. J.; Vinayak, R. V.; Wood, S. G. Solvent, Not Palladium Oxidadon State, Is the Primary Determinant for Successful Coupling of Terminal Alkynes with Iodo-nucleosides Tetrahedron Lett. 1990, 26, 3731-3734.
    • (1990) Tetrahedron Lett , vol.26 , pp. 3731-3734
    • Robins, M.J.1    Vinayak, R.V.2    Wood, S.G.3
  • 30
    • 27544440920 scopus 로고
    • Efficient Conversion of 5-Iodo to 5-Alkynyl and Derived 5-Subsdtuted Uracil Bases and Nucleosides
    • Robins, M. J.; Barr, P. J. Efficient Conversion of 5-Iodo to 5-Alkynyl and Derived 5-Subsdtuted Uracil Bases and Nucleosides. J. Org. Chem. 1983, 48, 1854-1862.
    • (1983) J. Org. Chem , vol.48 , pp. 1854-1862
    • Robins, M.J.1    Barr, P.J.2
  • 31
    • 0019381631 scopus 로고
    • Smooth and Efficient Palladium-Copper Catalyzed Coupling of Terminal Alkynes with 5-Iodouracil Nucleosides
    • Robins, M. J.; Barr, P. J. Smooth and Efficient Palladium-Copper Catalyzed Coupling of Terminal Alkynes with 5-Iodouracil Nucleosides. Tetrahedron Lett. 1981, 22, 421-424.
    • (1981) Tetrahedron Lett , vol.22 , pp. 421-424
    • Robins, M.J.1    Barr, P.J.2
  • 32
    • 0006498768 scopus 로고
    • Incorporation of 5-Substituted Uracil Derivatives into Nucleic Acids. III. Synthesis of 5-Substituted Uracil Derivatives from 5-Acetyluracil
    • Bleackley, R. C.; Jones, A.; Walker, R. T. Incorporation of 5-Substituted Uracil Derivatives into Nucleic Acids. III. Synthesis of 5-Substituted Uracil Derivatives from 5-Acetyluracil. Tetrahedron 1976, 32, 2795-2797.
    • (1976) Tetrahedron , vol.32 , pp. 2795-2797
    • Bleackley, R.C.1    Jones, A.2    Walker, R.T.3
  • 33
    • 22244433929 scopus 로고    scopus 로고
    • Janeba, Z.; Balzarini, J.; Andrei, G.; Snoeck, R.; De Clercq, E.; Robins, M. J. Synthesis and Biological Evaluation of Acyclic 3-[(2-Hydroxyethoxy) methyl] Analogues of Antiviral Furo- and Pyrrolo-[2,3-d]pyrimidine Nucleosides. J. Med. Chem. 2005, 48, 4690-4696.
    • Janeba, Z.; Balzarini, J.; Andrei, G.; Snoeck, R.; De Clercq, E.; Robins, M. J. Synthesis and Biological Evaluation of Acyclic 3-[(2-Hydroxyethoxy) methyl] Analogues of Antiviral Furo- and Pyrrolo-[2,3-d]pyrimidine Nucleosides. J. Med. Chem. 2005, 48, 4690-4696.
  • 34
    • 30444456685 scopus 로고    scopus 로고
    • Robins, M. J.; Miranda, K.; Rajwanshi, V. K.; Peterson, M. A.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Synthesis and Biological Evaluation of 6-(Alkyn-1-yl)furo[2,3-d]pyrimidin-2(3H)-one Base and Nucleoside Derivatives. J. Med. Chem. 2006, 49, 391-398.
    • Robins, M. J.; Miranda, K.; Rajwanshi, V. K.; Peterson, M. A.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Synthesis and Biological Evaluation of 6-(Alkyn-1-yl)furo[2,3-d]pyrimidin-2(3H)-one Base and Nucleoside Derivatives. J. Med. Chem. 2006, 49, 391-398.
  • 35
    • 0022450584 scopus 로고    scopus 로고
    • De Clercq, E.; Holý, A.; Rosenberg, I.; Sakuma, T.; Balzarini, J.; Maudgal, P. C. A Novel Selective Broad-Spectrum Anti-DNA Virus Agent. Nature 1986, 323, 464-467.
    • De Clercq, E.; Holý, A.; Rosenberg, I.; Sakuma, T.; Balzarini, J.; Maudgal, P. C. A Novel Selective Broad-Spectrum Anti-DNA Virus Agent. Nature 1986, 323, 464-467.
  • 36
    • 0025979184 scopus 로고
    • 9-(2-Phosphonyl- methoxyethyl) Adenine (PMEA) Effectively Inhibits Retrovirus Replication in Vitro and Simian Immunodeficiency Virus Infection in Rhesus Monkeys
    • Balzarini, J.; Naesens, L.; Slachmuylders, J.; Niphuis, H.; Rosenberg, I.; Holý, A.; Schellekens, H.; De Clercq, E. 9-(2-Phosphonyl- methoxyethyl) Adenine (PMEA) Effectively Inhibits Retrovirus Replication in Vitro and Simian Immunodeficiency Virus Infection in Rhesus Monkeys. AIDS 1991, 5, 21-28.
    • (1991) AIDS , vol.5 , pp. 21-28
    • Balzarini, J.1    Naesens, L.2    Slachmuylders, J.3    Niphuis, H.4    Rosenberg, I.5    Holý, A.6    Schellekens, H.7    De Clercq, E.8


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