메뉴 건너뛰기




Volumn 43, Issue 6, 2000, Pages 1180-1186

Doubly homologated dihalovinyl and acetylene analogues of adenosine: Synthesis, interaction with S-adenosyl-L-homocysteine hydrolase, and antiviral and cytostatic effects

Author keywords

[No Author keywords available]

Indexed keywords

9 (5,6,7 TRIDEOXY BETA DEXTRO RIBO HEPT 6 YNFURANOSYL)ADENINE; 9 (7 BROMO 5,6,7 TRIDEOXY 7 FLUORO BETA DEXTRO RIBO HEPT 6 ENOFURANOSYL)ADENINE; 9 (7,7 DIBROMO 5,6,7 TRIDEOXY BETA DEXTRO RIBO HEPT 6 ENOFURANOSYL)ADENINE; ADENOSINE DERIVATIVE; ANTIVIRUS AGENT; UNCLASSIFIED DRUG;

EID: 0034704823     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990486y     Document Type: Article
Times cited : (19)

References (35)
  • 1
    • 77956844792 scopus 로고    scopus 로고
    • Design and synthesis of S-adenosylhomocysteine hydrolase inhibitors as broad-spectrum antiviral agents
    • De Clercq, E., Ed.; JAI Press: Greenwich
    • Yuan, C.-S.; Liu, S.; Wnuk, S. F.; Robins, M. J.; Borchardt, R. T. Design and Synthesis of S-Adenosylhomocysteine Hydrolase Inhibitors as Broad-Spectrum Antiviral Agents. In Advances in Antiviral Drug Design; De Clercq, E., Ed.; JAI Press: Greenwich, 1996; Vol. 2, pp 41-88.
    • (1996) Advances in Antiviral Drug Design , vol.2 , pp. 41-88
    • Yuan, C.-S.1    Liu, S.2    Wnuk, S.F.3    Robins, M.J.4    Borchardt, R.T.5
  • 2
    • 0020284631 scopus 로고
    • Pharmacological and biochemical aspects of S-adenosylhomocysteine and S-adenosylhomocysteine hydrolase
    • (a) Ueland, P. M. Pharmacological and Biochemical Aspects of S-Adenosylhomocysteine and S-Adenosylhomocysteine Hydrolase, Pharmacol. Rev. 1982, 34, 223-253.
    • (1982) Pharmacol. Rev. , vol.34 , pp. 223-253
    • Ueland, P.M.1
  • 3
    • 0031934077 scopus 로고    scopus 로고
    • Biological effects of inhibitors of S-adenosylhomocysteine hydrolase
    • (b) Chiang, P. K. Biological Effects of Inhibitors of S-Adenosylhomocysteine Hydrolase. Pharmacol. Ther. 1998, 77, 115-134.
    • (1998) Pharmacol. Ther. , vol.77 , pp. 115-134
    • Chiang, P.K.1
  • 4
    • 0028893446 scopus 로고
    • Plasma homocysteine and arterial occlusive disease: A mini-review
    • (a) Malinow, M. R. Plasma Homocysteine and Arterial Occlusive Disease: A Mini-review. Clin. Chem. 1995, 41, 173-176.
    • (1995) Clin. Chem. , vol.41 , pp. 173-176
    • Malinow, M.R.1
  • 5
    • 0031543485 scopus 로고    scopus 로고
    • Homocysteine as a risk factor for artherosclerosis: A review
    • (b) Nehler, M. R.; Taylor, L. M.; Porter, J. M. Homocysteine as a Risk Factor for Artherosclerosis: A review. Cardiovasc. Surg. 1997, 559-567.
    • (1997) Cardiovasc. Surg. , pp. 559-567
    • Nehler, M.R.1    Taylor, L.M.2    Porter, J.M.3
  • 9
    • 0027209984 scopus 로고
    • Mechanism of inactivation of S-adenosyl-L-homocysteine hydrolase by fluorine-containing adenosine analogues
    • (b) Yuan, C.-S.; Yeh, J.; Liu, S.; Borchardt, R. T. Mechanism of Inactivation of S-Adenosyl-L-homocysteine Hydrolase by Fluorine-containing Adenosine Analogues. J. Biol. Chem. 1993, 268, 17030-17037.
    • (1993) J. Biol. Chem. , vol.268 , pp. 17030-17037
    • Yuan, C.-S.1    Yeh, J.2    Liu, S.3    Borchardt, R.T.4
  • 10
    • 0028104514 scopus 로고
    • Nucleic acid related compounds. 84. Synthesis of 6′(E and Z)-halohomovinyl derivatives of adenosine, inactivation of S-adenosyl-L-homocysteine hydrolase, and correlation of anticancer and antiviral potencies with enzyme inhibition
    • (a) Wnuk, S. F.; Yuan, C.-S.; Borchardt, R. T.; Balzarini, J.; De Clercq, E.; Robins, M. J. Nucleic Acid Related Compounds. 84. Synthesis of 6′(E and Z)-Halohomovinyl Derivatives of Adenosine, Inactivation of S-Adenosyl-L-homocysteine Hydrolase, and Correlation of Anticancer and Antiviral Potencies with Enzyme Inhibition. J. Med. Chem. 1994, 37, 3579-3587.
    • (1994) J. Med. Chem. , vol.37 , pp. 3579-3587
    • Wnuk, S.F.1    Yuan, C.-S.2    Borchardt, R.T.3    Balzarini, J.4    De Clercq, E.5    Robins, M.J.6
  • 11
    • 0028268586 scopus 로고
    • Mechanism of inactivation of S-adenosylhomocysteine hydrolase by (E)-5′,6′-Didehydro-6′-deoxy-6′-halohomoadenosines
    • (b) Yuan, C.-S.; Liu, S.; Wnuk, S. F.; Robins, M. J.; Borchardt, R. T. Mechanism of Inactivation of S-Adenosylhomocysteine Hydrolase by (E)-5′,6′-Didehydro-6′-Deoxy-6′-Halohomoadenosines. Biochemistry 1994, 33, 3758-3765,
    • (1994) Biochemistry , vol.33 , pp. 3758-3765
    • Yuan, C.-S.1    Liu, S.2    Wnuk, S.F.3    Robins, M.J.4    Borchardt, R.T.5
  • 12
    • 0028079891 scopus 로고
    • (E)-5′,6′-didehydro-6′-deoxy-6′- fluorohomoadenosine: A substrate that measures the hydrolytic activity of S-adenosylhomocysteine hydrolase
    • (c) Yuan, C.-S.; Wnuk, S. F.; Liu, S.; Robins, M. J.; Borchardt, R. T. (E)-5′,6′-Didehydro-6′-Deoxy-6′-Fluorohomoadenosine: A Substrate That Measures The Hydrolytic Activity of S-Adenosylhomocysteine Hydrolase. Biochemistry 1994, 33, 12305-12311.
    • (1994) Biochemistry , vol.33 , pp. 12305-12311
    • Yuan, C.-S.1    Wnuk, S.F.2    Liu, S.3    Robins, M.J.4    Borchardt, R.T.5
  • 13
    • 0031006943 scopus 로고    scopus 로고
    • Anticancer and antiviral effects and inactivation of S-adenosyl-L-homocysteine hydrolase with 5′-carboxaldehydes and oximes synthesized from adenosine and sugar-modified analogues
    • (a) Wnuk, S. F.; Yuan, C.-S.; Borchardt, R. T.; Balzarini, J.; De Clercq, E.; Robins, M. J. Anticancer and Antiviral Effects and Inactivation of S-Adenosyl-L-homocysteine Hydrolase with 5′-Carboxaldehydes and Oximes Synthesized from Adenosine and Sugar-Modified Analogues. J. Med. Chem. 1997, 40, 1608-1618.
    • (1997) J. Med. Chem. , vol.40 , pp. 1608-1618
    • Wnuk, S.F.1    Yuan, C.-S.2    Borchardt, R.T.3    Balzarini, J.4    De Clercq, E.5    Robins, M.J.6
  • 14
    • 0031195042 scopus 로고    scopus 로고
    • The mechanism of inactivation of human placental S-adenosylhomocysteine hydrolase by (E)-4′,5′-didehydro-5′-methoxyadenosine (DMAO) and adenosine 5′-carboxaldehyde oxime (ACAO)
    • (b) Huang, H.; Yuan, C.-S.; Wnuk, S. F.; Robins, M. J.; Borchardt, R. T. The Mechanism of Inactivation of Human Placental S-Adenosylhomocysteine Hydrolase by (E)-4′,5′-Didehydro-5′-methoxyadenosine (DMAO) and Adenosine 5′-carboxaldehyde Oxime (ACAO). Arch. Biochem. Biophys. 1997, 343, 109-117.
    • (1997) Arch. Biochem. Biophys. , vol.343 , pp. 109-117
    • Huang, H.1    Yuan, C.-S.2    Wnuk, S.F.3    Robins, M.J.4    Borchardt, R.T.5
  • 15
    • 0032548968 scopus 로고    scopus 로고
    • Nucleic acid related compounds. 101. S-adenosyl-L-homocysteine hydrolase does not hydrate (5′-fluoro)vinyl or (6′-halo)homovinyl analogues derived from 3′-deoxyadenosine or 3′-(chloro or fluoro)-3′-deoxyadenosine
    • Robins, M. J.; Neschadimenko, V.; Ro, B.-O.; Yuan, C.-S.; Borchardt, R. T.; Wnuk, S. F. Nucleic Acid Related Compounds. 101. S-Adenosyl-L-homocysteine Hydrolase Does Not Hydrate (5′-Fluoro)vinyl or (6′-Halo)homovinyl Analogues Derived from 3′-Deoxyadenosine or 3′-(Chloro or Fluoro)-3′-deoxyadenosine. J. Org. Chem. 1998, 63, 1205-1211.
    • (1998) J. Org. Chem. , vol.63 , pp. 1205-1211
    • Robins, M.J.1    Neschadimenko, V.2    Ro, B.-O.3    Yuan, C.-S.4    Borchardt, R.T.5    Wnuk, S.F.6
  • 16
    • 0032581608 scopus 로고    scopus 로고
    • Discovery of type II (covalent) inactivation of S-adenosyl-L-homocysteine hydrolase. Synthesis and evaluation of dihalohomovinyl nucleoside analogues derived from adenosine
    • (a) Wnuk, S. F.; Mao, Y.; Yuan, C.-S.; Borchardt, R. T.; Andrei, J.; Balzarini, J.; De Clercq, E.; Robins, M. J. Discovery of Type II (Covalent) Inactivation of S-Adenosyl-L-homocysteine Hydrolase. Synthesis and Evaluation of Dihalohomovinyl Nucleoside Analogues Derived from Adenosine. J. Med. Chem. 1998, 41, 3078-3083.
    • (1998) J. Med. Chem. , vol.41 , pp. 3078-3083
    • Wnuk, S.F.1    Mao, Y.2    Yuan, C.-S.3    Borchardt, R.T.4    Andrei, J.5    Balzarini, J.6    De Clercq, E.7    Robins, M.J.8
  • 17
    • 0032540945 scopus 로고    scopus 로고
    • A novel mechanism-based inhibitor (6′-bromo-5′,6′-didehydro-6′-deoxy-6′- fluorohomoadenosine) that covalently modifies human placental S-adenosylhomocysteine hydrolase
    • (b) Yuan, C.-S.; Wnuk, S. F.; Robins, M. J.; Borchardt, R. T. A Novel Mechanism-Based Inhibitor (6′-Bromo-5′,6′-didehydro-6′-deoxy-6′- fluorohomoadenosine) That Covalently Modifies Human Placental S-Adenosylhomocysteine Hydrolase. J. Biol. Chem. 1998, 273, 18191-18197.
    • (1998) J. Biol. Chem. , vol.273 , pp. 18191-18197
    • Yuan, C.-S.1    Wnuk, S.F.2    Robins, M.J.3    Borchardt, R.T.4
  • 18
    • 0025941439 scopus 로고
    • 9-(5′,6′-dideoxy-β-D-ribo-hex-5′-ynofuranosyl) adenine, a novel irreversible inhibitor of S-adenosylhomocysteine hydrolase
    • (a) Parry, R. J.; Muscate, A.; Askonas, L. J. 9-(5′,6′-Dideoxy-β-D-ribo-hex-5′-ynofuranosyl)adenine, a Novel Irreversible Inhibitor of S-Adenosylhomocysteine Hydrolase. Biochemistry 1991, 30, 9988-9997.
    • (1991) Biochemistry , vol.30 , pp. 9988-9997
    • Parry, R.J.1    Muscate, A.2    Askonas, L.J.3
  • 19
    • 0029088339 scopus 로고
    • Nucleosides and nucleotides. 142. An alternative synthesis of 9-(5,6-dideoxy-β-D-ribo-hex-5-ynofuranosyl)adenine and its antiviral activity
    • (b) Matsuda, A.; Kosaki, H.; Yoshimura, Y.; Shuto, S.; Ashida, N.; Konno, K.; Shigeta, S. Nucleosides and Nucleotides. 142. An Alternative Synthesis of 9-(5,6-Dideoxy-β-D-ribo-hex-5-ynofuranosyl)adenine and its Antiviral Activity. Bioorg. Med. Chem. Lett. 1995, 5, 1685-1688.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 1685-1688
    • Matsuda, A.1    Kosaki, H.2    Yoshimura, Y.3    Shuto, S.4    Ashida, N.5    Konno, K.6    Shigeta, S.7
  • 20
    • 0032563907 scopus 로고    scopus 로고
    • Inactivation of S-adenosyl-L-homocysteine hydrolase and antiviral activitiy with 5′,5′,6′,6′-tetradehydro-6′-deoxy-6′- halohomoadenosine analogues (4′-haloacetylene analogues derived from adenosine)
    • Robins, M. J.; Wnuk, S. F.; Yang, X.; Yuan, C.-S.; Borchardt, R. T.; Balzarini, J.; De Clercq, E. Inactivation of S-Adenosyl-L-homocysteine Hydrolase and Antiviral Activitiy with 5′,5′,6′,6′-Tetradehydro-6′-Deoxy-6′- Halohomoadenosine Analogues (4′-Haloacetylene Analogues Derived from Adenosine). J. Med. Chem. 1998, 41, 3857-3864.
    • (1998) J. Med. Chem. , vol.41 , pp. 3857-3864
    • Robins, M.J.1    Wnuk, S.F.2    Yang, X.3    Yuan, C.-S.4    Borchardt, R.T.5    Balzarini, J.6    De Clercq, E.7
  • 21
    • 0031947190 scopus 로고    scopus 로고
    • Structure determination of seleno-methionyl S-adenosylhomocysteine hydrolase using data at a single wavelength
    • Turner, M. A.; Yuan, C.-S.; Borchardt, R. T.; Hershfield, M. S.; Smith, G. D.; Howell, P. L. Structure Determination of Seleno-methionyl S-Adenosylhomocysteine Hydrolase using data at a single wavelength. Nature Struct. Biol. 1998, 5, 369-376.
    • (1998) Nature Struct. Biol. , vol.5 , pp. 369-376
    • Turner, M.A.1    Yuan, C.-S.2    Borchardt, R.T.3    Hershfield, M.S.4    Smith, G.D.5    Howell, P.L.6
  • 22
    • 84985239894 scopus 로고
    • Darstellung and konformationszuordnung einiger 5′-homologer adenosinderivate
    • Hollmann, J.; Schlimme, E. Darstellung and Konformationszuordnung einiger 5′-homologer Adenosinderivate. (Synthesis and Conformational Analysis of Some 5′-Homoadenosine Derivatives.) Liebigs Ann. Chem. 1984, 98-107.
    • (1984) Liebigs Ann. Chem. , pp. 98-107
    • Hollmann, J.1    Schlimme, E.2
  • 23
    • 0030947640 scopus 로고    scopus 로고
    • Elimination of chlorine (radical) or tosylate (anion) from C2′ of nucleoside C3′ free radicals as model reactions postulated to occur at the active site of ribonucleotide reductases
    • (a) Robins, M. J.; Guo, Z.; Wnuk, S. F. Elimination of Chlorine (Radical) or Tosylate (Anion) from C2′ of Nucleoside C3′ Free Radicals as Model Reactions Postulated To Occur at the Active Site of Ribonucleotide Reductases. J. Am. Chem. Soc. 1997, 119, 3637-3638.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 3637-3638
    • Robins, M.J.1    Guo, Z.2    Wnuk, S.F.3
  • 24
    • 0033599335 scopus 로고    scopus 로고
    • Biomimetic simulation of free radical-initiated cascade reactions postulated to occur at the active site of ribonucleotide reductases
    • (b) Robins, M. J.; Guo, Z.; Samano, M. C.; Wnuk, S. F. Biomimetic Simulation of Free Radical-Initiated Cascade Reactions Postulated to Occur at the Active Site of Ribonucleotide Reductases. J. Am. Chem. Soc. 1999, 121, 1425-1433.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1425-1433
    • Robins, M.J.1    Guo, Z.2    Samano, M.C.3    Wnuk, S.F.4
  • 25
    • 0033617228 scopus 로고    scopus 로고
    • Biomimetic modeling of the abstraction of H3′ by ribonucleotide reductases. 1,5-hydrogen atom transfer of H3 to aminyl and oxyl, but not thiyl, free radicals in homoribofuranose derivatives
    • (c) Guo, Z.; Samano, M. C.; Krzykawski J. W.; Wnuk, S. F.; Ewing, G. J.; Robins, M. J. Biomimetic Modeling of the Abstraction of H3′ by Ribonucleotide Reductases. 1,5-Hydrogen Atom Transfer of H3 to Aminyl and Oxyl, but not Thiyl, Free Radicals in Homoribofuranose Derivatives. Tetrahedron 1999, 55, 5705-5718.
    • (1999) Tetrahedron , vol.55 , pp. 5705-5718
    • Guo, Z.1    Samano, M.C.2    Krzykawski J, W.3    Wnuk, S.F.4    Ewing, G.J.5    Robins, M.J.6
  • 26
    • 85008105974 scopus 로고
    • Regioselective mono-oxidation of nonprotected carbohydrates by brominolysis of the tin intermediates
    • Tsuda, Y.; Hanajima, M.; Matsuhira, N.; Okuno, Y.; Kanemitsu, K. Regioselective Mono-oxidation of Nonprotected Carbohydrates by Brominolysis of the Tin Intermediates. Chem. Pharm. Bull. 1989, 37, 2344-2350.
    • (1989) Chem. Pharm. Bull. , vol.37 , pp. 2344-2350
    • Tsuda, Y.1    Hanajima, M.2    Matsuhira, N.3    Okuno, Y.4    Kanemitsu, K.5
  • 27
    • 0016375205 scopus 로고
    • Novel analogues of nucleoside 3′,5′-cyclic phosphates. I. 5′-mono-and dimethyl analogues of adenosine 3′,5′-cyclic phosphate
    • Ranganathan, R. S.; Jones, G. H.; Moffatt, J. G. Novel Analogues of Nucleoside 3′,5′-Cyclic Phosphates. I. 5′-Mono-and Dimethyl Analogues of Adenosine 3′,5′-Cyclic Phosphate. J. Org. Chem. 1974, 39, 290-298.
    • (1974) J. Org. Chem. , vol.39 , pp. 290-298
    • Ranganathan, R.S.1    Jones, G.H.2    Moffatt, J.G.3
  • 28
    • 0000344537 scopus 로고
    • A synthetic method for formyl → ethynyl conversion (RCHO → RC≡CH or RC≡CR′)
    • Corey, E. J.; Fuchs, P. L. A Synthetic Method for Formyl → Ethynyl Conversion (RCHO → RC≡CH or RC≡CR′). Tetrahedron Lett. 1972, 3769-3772.
    • (1972) Tetrahedron Lett. , pp. 3769-3772
    • Corey, E.J.1    Fuchs, P.L.2
  • 29
    • 0018707351 scopus 로고
    • Synthetic nucleosides and nucleotides. XIII. Stannic chloride catalyzed ribosylation of several 6-substituted purines
    • Saneyoshi, M.; Satoh, E. Synthetic Nucleosides and Nucleotides. XIII. Stannic Chloride Catalyzed Ribosylation of Several 6-Substituted Purines. Chem. Pharm. Bull. 1979, 27, 2518-2521.
    • (1979) Chem. Pharm. Bull. , vol.27 , pp. 2518-2521
    • Saneyoshi, M.1    Satoh, E.2
  • 30
    • 0018272938 scopus 로고
    • Acetylenic nucleosides. 1. Synthesis of 1-(5,6-dideoxy-β-D-ribo-hex-5-ynofuranosyl)uracil and 1-(2,5,6-trideoxy-β-D-erythro-hex-5-ynofuranosyl)-5-methyluracil
    • Sharma, R. A.; Bobek, M. Acetylenic Nucleosides. 1. Synthesis of 1-(5,6-Dideoxy-β-D-ribo-hex-5-ynofuranosyl)uracil and 1-(2,5,6-Trideoxy-β-D-erythro-hex-5-ynofuranosyl)-5-methyluracil. J. Org. Chem. 1978, 43, 367-369.
    • (1978) J. Org. Chem. , vol.43 , pp. 367-369
    • Sharma, R.A.1    Bobek, M.2
  • 31
    • 0023235758 scopus 로고
    • S-adenosylhomocysteine hydrolase inhibitors as broad spectrum antiviral agents
    • De Clercq, E. S-Adenosylhomocysteine Hydrolase Inhibitors as Broad Spectrum Antiviral Agents. Biochem. Pharmacol. 1987, 36, 2567-2575.
    • (1987) Biochem. Pharmacol. , vol.36 , pp. 2567-2575
    • De Clercq, E.1
  • 32
    • 0029961930 scopus 로고    scopus 로고
    • Chemical modification and site-directed mutagenesis of cysteine residues in human placental S-adenosylhomocysteine hydrolase
    • Yuan, C.-S.; Ault-Riche, D.; Borchardt, R. T. Chemical Modification and Site-directed Mutagenesis of Cysteine Residues in Human Placental S-Adenosylhomocysteine Hydrolase. J. Biol. Chem. 1996, 271, 28009-28016.
    • (1996) J. Biol. Chem. , vol.271 , pp. 28009-28016
    • Yuan, C.-S.1    Ault-Riche, D.2    Borchardt, R.T.3
  • 35
    • 0027174364 scopus 로고
    • Inhibitory activity of S-adenosylhomocysteine hydrolase inhibitors against human cytomegalovirus replication
    • (c) Snoeck, R.; Andrei, G.; Neyts, J.; Schols, D.; Cools, M.; Balzarini, J.; De Clercq, E. Inhibitory Activity of S-Adenosylhomocysteine Hydrolase Inhibitors against Human Cytomegalovirus Replication. Antiviral Res. 1993, 21, 197-216.
    • (1993) Antiviral Res. , vol.21 , pp. 197-216
    • Snoeck, R.1    Andrei, G.2    Neyts, J.3    Schols, D.4    Cools, M.5    Balzarini, J.6    De Clercq, E.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.