메뉴 건너뛰기




Volumn 45, Issue 22, 2002, Pages 4888-4898

Stereoselective synthesis and antiviral activity of d-2′,3′-didehydro-2′,3′-dideoxy-2′-fluoro-4 ′-thionucleosides

Author keywords

[No Author keywords available]

Indexed keywords

(2,3 DIDEOXY 2,3 DIDEHYDRO 2 FLUORO 4 THIO BETA DEXTRO RIBOFURANOSYL) 2 FLUOROADENOSINE; (2,3 DIDEOXY 2,3 DIDEHYDRO 2 FLUORO 4 THIO BETA DEXTRO RIBOFURANOSYL) 5 FLUOROCYTOSINE; (2,3 DIDEOXY 2,3 DIDEHYDRO 2 FLUORO 4 THIO BETA DEXTRO RIBOFURANOSYL)ADENINE; (2,3 DIDEOXY 2,3 DIDEHYDRO 2 FLUORO 4 THIO BETA DEXTRO RIBOFURANOSYL)CYTOSINE; ANTIVIRUS AGENT; LAMIVUDINE; METHIONINE; NUCLEOSIDE DERIVATIVE; SULFUR; UNCLASSIFIED DRUG;

EID: 0037168035     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020246+     Document Type: Article
Times cited : (48)

References (46)
  • 4
    • 0029559244 scopus 로고
    • Viral resistance and the selection of antiretroviral combinations
    • Larder, B. A. Viral resistance and the selection of antiretroviral combinations. J. Acquir. Immune Defic. Syndr. Hum. Retrovirol. 1995, 10 (Suppl. 1), S28-S33.
    • (1995) J. Acquir. Immune Defic. Syndr. Hum. Retrovirol. , vol.10 , Issue.SUPPL. 1
    • Larder, B.A.1
  • 5
    • 0023267580 scopus 로고
    • Inhibitory effect of 2′,3′-didehydro-2′,3′-dideoxynucleosides on infectivity, cytopathic effects and replication of human immunodeficiency virus
    • Hamamoto, Y.; Yamamoto, N.; Matsui, T.; Matsuda, A.; Ueda, T.; Yamamoto, N. Inhibitory effect of 2′,3′-didehydro-2′,3′- dideoxynucleosides on infectivity, cytopathic effects and replication of human immunodeficiency virus. Antimicrob. Agents Chemother. 1987, 31, 907-910.
    • (1987) Antimicrob. Agents Chemother. , vol.31 , pp. 907-910
    • Hamamoto, Y.1    Yamamoto, N.2    Matsui, T.3    Matsuda, A.4    Ueda, T.5    Yamamoto, N.6
  • 6
    • 0023196616 scopus 로고
    • Potent and selective in vitro activity of 3′-deoxyadenosine, deoxythymidine-2′-ene (3′-deoxy-2′,3′-didehydrothymidine) against human immunodeficiency virus in vitro
    • Lin, T.-S.; Schinazi, R. F.; Prusoff, W. H. Potent and selective in vitro activity of 3′-deoxyadenosine, deoxythymidine-2′-ene (3′-deoxy-2′,3′-didehydrothymidine) against human immunodeficiency virus in vitro. Biochem. Pharmacol. 1987, 36, 2713-2718.
    • (1987) Biochem. Pharmacol. , vol.36 , pp. 2713-2718
    • Lin, T.-S.1    Schinazi, R.F.2    Prusoff, W.H.3
  • 8
    • 0029881506 scopus 로고    scopus 로고
    • Design and synthesis of 2′,3′-dideoxy-2′,3′-didehydro-(β-L-cytidine (β-L-d4C) and 2′,3′-dideoxy2′,3′-didehydro-β -L-5-fluorocytidine (β-L-Fd4C), two exceptionally potent inhibitors of hepatitis B virus (HBV) and potent inhibitors of human immunodeficiency virus (HIV) in vitro
    • Lin, T.-S.; Luo, M. Z.; Liu, M. C.; Zhu, Y. L.; Gullen, E.; Dutchman, G. E.; Cheng, Y.-C. Design and synthesis of 2′,3′-dideoxy-2′,3′-didehydro-(β-L-cytidine (β-L-d4C) and 2′,3′-dideoxy2′,3′-didehydro-β -L-5-fluorocytidine (β-L-Fd4C), two exceptionally potent inhibitors of hepatitis B virus (HBV) and potent inhibitors of human immunodeficiency virus (HIV) in vitro. J. Med. Chem. 1996, 39, 1757-1759.
    • (1996) J. Med. Chem. , vol.39 , pp. 1757-1759
    • Lin, T.-S.1    Luo, M.Z.2    Liu, M.C.3    Zhu, Y.L.4    Gullen, E.5    Dutchman, G.E.6    Cheng, Y.-C.7
  • 10
    • 0030945276 scopus 로고    scopus 로고
    • Combination of mutations in human immunodeficiency virus type 1 reverse transcriptase required for resistance to the carbocyclic nucleoside 1592U89
    • Tisdale, M.; Alnadaf, T.; Cousens, D. Combination of mutations in human immunodeficiency virus type 1 reverse transcriptase required for resistance to the carbocyclic nucleoside 1592U89. Antimicrob. Agents Chemother. 1997, 41, 1094-1098.
    • (1997) Antimicrob. Agents Chemother. , vol.41 , pp. 1094-1098
    • Tisdale, M.1    Alnadaf, T.2    Cousens, D.3
  • 11
    • 0033535597 scopus 로고    scopus 로고
    • Synthesis and anti-HIV and anti-HBV activities of 2′-fluoro-2′,3′-unsaturated L-nucleosides
    • (a) Lee, K.; Choi, Y.; Gullen, E.; Schlueter-Wirtz, S.; Schinazi, R. F.; Cheng, Y.-C.; Chu, C. K. Synthesis and anti-HIV and anti-HBV activities of 2′-fluoro-2′,3′-unsaturated L-nucleosides. J. Med. Chem. 1999, 42, 1320-1328.
    • (1999) J. Med. Chem. , vol.42 , pp. 1320-1328
    • Lee, K.1    Choi, Y.2    Gullen, E.3    Schlueter-Wirtz, S.4    Schinazi, R.F.5    Cheng, Y.-C.6    Chu, C.K.7
  • 12
    • 0037075785 scopus 로고    scopus 로고
    • Structure-activity relationships of 2′-fluoro-2′,3′-unsaturated D-nucleosides as anti-HIV-1 agents
    • (b) Lee, K.; Choi, Y.; Gumina, G.; Zhou, W.; Schinazi, R. F.; Chu, C. K. Structure-activity relationships of 2′-fluoro-2′,3′-unsaturated D-nucleosides as anti-HIV-1 agents. J. Med. Chem. 2002, 45, 1313-1320.
    • (2002) J. Med. Chem. , vol.45 , pp. 1313-1320
    • Lee, K.1    Choi, Y.2    Gumina, G.3    Zhou, W.4    Schinazi, R.F.5    Chu, C.K.6
  • 13
    • 0000306137 scopus 로고
    • Synthesis of 4-thio-D-&L-ribofuranose and corresponding adenine nucleosides
    • Reist, E. J.; Gueffroy, D. E.; Goodman, L. Synthesis of 4-thio-D-&L-ribofuranose and corresponding adenine nucleosides. J. Am. Chem. Soc. 1964, 86, 5658-5663.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 5658-5663
    • Reist, E.J.1    Gueffroy, D.E.2    Goodman, L.3
  • 14
    • 0015223917 scopus 로고
    • 4-Thio-D-arabinofuranosylpyrimidine nucleosides
    • (a) Whistler, R. L.; Doner, L. W.; Nayak, U. G. 4-Thio-D- arabinofuranosylpyrimidine nucleosides. J. Org. Chem. 1971, 36, 108-110.
    • (1971) J. Org. Chem. , vol.36 , pp. 108-110
    • Whistler, R.L.1    Doner, L.W.2    Nayak, U.G.3
  • 15
    • 0016723031 scopus 로고
    • Synthesis and biological activity of 5-fluoro-4′-thiouridine and some related nucleosides
    • (b) Bobek, M.; Bloch, A.; Parthasarathy, R.; Whistler, R. L. Synthesis and biological activity of 5-fluoro-4′-thiouridine and some related nucleosides. J. Med. Chem. 1975, 18, 784-787.
    • (1975) J. Med. Chem. , vol.18 , pp. 784-787
    • Bobek, M.1    Bloch, A.2    Parthasarathy, R.3    Whistler, R.L.4
  • 16
    • 0014231434 scopus 로고
    • Neighboring-group participation. Preparation of dithiopentose sugars via a thioacylonium ion intermediate
    • Reist, E. J.; Fisher, L. V.; Gueffroy, E.; Goodman, L. Neighboring-group participation. Preparation of dithiopentose sugars via a thioacylonium ion intermediate. J. Org. Chem. 1968, 33, 189-192.
    • (1968) J. Org. Chem. , vol.33 , pp. 189-192
    • Reist, E.J.1    Fisher, L.V.2    Gueffroy, E.3    Goodman, L.4
  • 17
    • 0016366112 scopus 로고
    • Preparation and antitumor activity of 4′-thio analogues of 2,2′-anhydro-1-β-D-arabinofuranosylcytosine
    • Ototani, N.; Whistler, R. L. Preparation and antitumor activity of 4′-thio analogues of 2,2′-anhydro-1-β-D-arabinofuranosylcytosine. J. Med. Chem. 1974, 17, 535-537.
    • (1974) J. Med. Chem. , vol.17 , pp. 535-537
    • Ototani, N.1    Whistler, R.L.2
  • 18
    • 0011125471 scopus 로고
    • Townsend, L.; Tipson, R. S., Eds.; John Wiley & Sons: New York
    • Fu, Y.-L.; Bobek, M. In Nucleic Aicd Chemistry; Townsend, L.; Tipson, R. S., Eds.; John Wiley & Sons: New York, 1978; pp 317-323.
    • (1978) Nucleic Aicd Chemistry , pp. 317-323
    • Fu, Y.-L.1    Bobek, M.2
  • 19
    • 0025827985 scopus 로고
    • The synthesis and antiviral properties of E-5-(2-bromovinyl)-4′-thio-2′-deoxyuridine
    • (a) Dyson, M. R.; Coe, P. L.; Walker, R. T. The synthesis and antiviral properties of E -5-(2-bromovinyl)-4′-thio-2′-deoxyuridine. J. Chem. Soc., Chem. Commun. 1991, 741-742.
    • (1991) J. Chem. Soc., Chem. Commun. , pp. 741-742
    • Dyson, M.R.1    Coe, P.L.2    Walker, R.T.3
  • 20
    • 0026012222 scopus 로고
    • The synthesis and antiviral activity of some 4′-thio-2′-deoxy nucleoside analogues
    • (b) Dyson, M. R.; Coe, P. L.; Walker, R. T. The synthesis and antiviral activity of some 4′-thio-2′-deoxy nucleoside analogues. J. Med. Chem. 1991, 34, 2782-2786.
    • (1991) J. Med. Chem. , vol.34 , pp. 2782-2786
    • Dyson, M.R.1    Coe, P.L.2    Walker, R.T.3
  • 21
    • 0026045160 scopus 로고
    • Synthesis and biological activity of 2′-deoxy-4′-thiopyrimidine nucleosides
    • Secrist, J. A.; Tiwari, K. N.; Riordan, J. M.; Montgomery, J. A. Synthesis and biological activity of 2′-deoxy-4′-thiopyrimidine nucleosides. J. Med. Chem. 1991, 34, 2361-2366.
    • (1991) J. Med. Chem. , vol.34 , pp. 2361-2366
    • Secrist, J.A.1    Tiwari, K.N.2    Riordan, J.M.3    Montgomery, J.A.4
  • 22
    • 0026095737 scopus 로고
    • Stereocontrolled preparation of cyclic xanthate - A novel synthetic route to 4-thiofuranose and 4′-thionucleoside
    • (a) Uenishi, J.; Motoyama, M.; Nishiyama, Y.; Wakabayashi, S. Stereocontrolled preparation of cyclic xanthate - A novel synthetic route to 4-thiofuranose and 4′-thionucleoside. J. Chem. Soc., Chem. Commun. 1991, 1421-1422.
    • (1991) J. Chem. Soc., Chem. Commun. , pp. 1421-1422
    • Uenishi, J.1    Motoyama, M.2    Nishiyama, Y.3    Wakabayashi, S.4
  • 23
    • 0028245909 scopus 로고
    • Syntheses and antitumor activities of D-2′-deoxy-4′-thio and L-2′-deoxy-4′-thio pyrimidine nucleosides
    • (b) Uenishi, J.; Takahashi, K.; Motoyama, M.; Akashi, H.; Sasaki, T. Syntheses and antitumor activities of D-2′-deoxy-4′-thio and L-2′-deoxy-4′-thio pyrimidine nucleosides. Nucleosides Nucleotides 1994, 13, 1347-1361.
    • (1994) Nucleosides Nucleotides , vol.13 , pp. 1347-1361
    • Uenishi, J.1    Takahashi, K.2    Motoyama, M.3    Akashi, H.4    Sasaki, T.5
  • 24
    • 0026551053 scopus 로고
    • Synthesis and anti-HIV activity of 4′-thio-2′,3′- dideoxynucleosides
    • Secrist, J. A.; Riggs, R. M.; Tiwari, K. N.; Montgomery, J. A. Synthesis and anti-HIV activity of 4′-thio-2′,3′- dideoxynucleosides. J. Med. Chem. 1992, 35, 533-538.
    • (1992) J. Med. Chem. , vol.35 , pp. 533-538
    • Secrist, J.A.1    Riggs, R.M.2    Tiwari, K.N.3    Montgomery, J.A.4
  • 29
    • 0021019292 scopus 로고
    • Phosphorolysis of (E)-5-(2-bromovinyl)-2′-deoxyuridine (BVDU) and other 5-substituted-2′-deoxyuridines by purified human thymidine phosphorylase and intact blood-platelets
    • (a) Desgranges, C.; Razaka, G.; Rabaud, M.; Bricaud, H.; Balzarini, J.; De Clercq, E. Phosphorolysis of (E)-5-(2-bromovinyl)-2′-deoxyuridine (BVDU) and other 5-substituted-2′-deoxyuridines by purified human thymidine phosphorylase and intact blood-platelets. Biochem. Pharmacol. 1983, 32, 3583-3590.
    • (1983) Biochem. Pharmacol. , vol.32 , pp. 3583-3590
    • Desgranges, C.1    Razaka, G.2    Rabaud, M.3    Bricaud, H.4    Balzarini, J.5    De Clercq, E.6
  • 31
    • 0028811637 scopus 로고
    • Synthesis and antiviral evaluation of enantiomeric 2′,3′-dideoxy- and 2′,3′-didehydro- 2′,3′-dideoxy-4′-thionucleosides
    • Young, R. J.; Shaw-Ponter, S.; Thomson, J. B.; Miller, J. A.; Cumming, J. G.; Pugh, A. W.; Rider, P. Synthesis and antiviral evaluation of enantiomeric 2′,3′-dideoxy- and 2′,3′-didehydro- 2′,3′-dideoxy-4′-thionucleosides. Bioorg. Med. Chem. Lett. 1995, 5, 2599-2604.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 2599-2604
    • Young, R.J.1    Shaw-Ponter, S.2    Thomson, J.B.3    Miller, J.A.4    Cumming, J.G.5    Pugh, A.W.6    Rider, P.7
  • 32
    • 0037165411 scopus 로고    scopus 로고
    • Synthesis and potent anti-HIV activity of L-2′,3′- didehydro-2′,3′-dideoxy-2′-fluoro-4′- thiocytidine
    • Choi, Y.; Choo, H.; Chong, Y.; Lee, S.; Olgen, S.; Schinazi, R. F.; Chu, C. K. Synthesis and potent anti-HIV activity of L-2′,3′- didehydro-2′,3′-dideoxy-2′-fluoro-4′- thiocytidine. Org. Lett. 2002, 4, 305-307.
    • (2002) Org. Lett. , vol.4 , pp. 305-307
    • Choi, Y.1    Choo, H.2    Chong, Y.3    Lee, S.4    Olgen, S.5    Schinazi, R.F.6    Chu, C.K.7
  • 33
    • 0034671040 scopus 로고    scopus 로고
    • A divergent synthesis of D-and L-carbocyclic 4′-fluoro-2′,3′-dideoxynucleosides as potential antiviral agents
    • Chong, Y.; Gumina, G.; Chu, C. K. A divergent synthesis of D-and L-carbocyclic 4′-fluoro-2′,3′-dideoxynucleosides as potential antiviral agents. Tetrahedron: Asymmetry 2000, 11, 4853-4875.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 4853-4875
    • Chong, Y.1    Gumina, G.2    Chu, C.K.3
  • 34
    • 0000857565 scopus 로고
    • A highly stereoselective glycosylation of 2-(phenylselenyl)-2,3-dideoxyribose derivative with thymine: Synthesis of 3′-deoxy-2′,3′-didehydrothymidine and 3′-deoxythymidine
    • Chu, C. K.; Babu, J. R.; Beach, W.; Ahn, S. K.; Huang, H.; Jeong, L. S.; Lee, S. J. A highly stereoselective glycosylation of 2-(phenylselenyl)-2,3-dideoxyribose derivative with thymine: Synthesis of 3′-deoxy-2′,3′-didehydrothymidine and 3′-deoxythymidine. J. Org. Chem. 1990, 55, 1418-1420.
    • (1990) J. Org. Chem. , vol.55 , pp. 1418-1420
    • Chu, C.K.1    Babu, J.R.2    Beach, W.3    Ahn, S.K.4    Huang, H.5    Jeong, L.S.6    Lee, S.J.7
  • 36
    • 0027285372 scopus 로고
    • Rapid in vitro selection of human immunodeficiency virus type 1 resistant to 3′-thiactidine inhibitors due to a mutation in the YMDD region of reverse transcriptase
    • Tisdale, M.; Kemp, S. D.; Parry, N. R.; Larder, B. A. Rapid in vitro selection of human immunodeficiency virus type 1 resistant to 3′-thiactidine inhibitors due to a mutation in the YMDD region of reverse transcriptase. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5653-5656.
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 5653-5656
    • Tisdale, M.1    Kemp, S.D.2    Parry, N.R.3    Larder, B.A.4
  • 37
    • 0032573488 scopus 로고    scopus 로고
    • Structure of a covalently trapped catalytic complex of HIV-1 reverse transcriptase: Implications for drug resistance
    • Huang, H.; Chopra, R.; Verdine, G. L.; Harrison, S. C. Structure of a covalently trapped catalytic complex of HIV-1 reverse transcriptase: Implications for drug resistance. Science 1998, 282, 1669-1675.
    • (1998) Science , vol.282 , pp. 1669-1675
    • Huang, H.1    Chopra, R.2    Verdine, G.L.3    Harrison, S.C.4
  • 38
    • 0035173806 scopus 로고    scopus 로고
    • Molecular modeling approach to understanding the mode of action of L-nucleosides as antiviral agents
    • Lee, K.; Chu, C. K. Molecular modeling approach to understanding the mode of action of L-nucleosides as antiviral agents. Antimicrob. Agents Chemother. 2001, 45, 138-144.
    • (2001) Antimicrob. Agents Chemother. , vol.45 , pp. 138-144
    • Lee, K.1    Chu, C.K.2
  • 39
    • 0035920856 scopus 로고    scopus 로고
    • Stereoselective cyclopropanation of 3-aryl-2-phosphonoacrylates induced by the (-)-8-phenylmenthyl group as a chiral auxiliary
    • References are cited therein
    • Takagi, R.; Nakamura, M.; Hashizume, M.; Kojima, S.; Ohkata, K. Stereoselective cyclopropanation of 3-aryl-2-phosphonoacrylates induced by the (-)-8-phenylmenthyl group as a chiral auxiliary. Tetrahedron lett. 2001, 42, 5891-5895. References are cited therein.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5891-5895
    • Takagi, R.1    Nakamura, M.2    Hashizume, M.3    Kojima, S.4    Ohkata, K.5
  • 41
    • 0040609327 scopus 로고    scopus 로고
    • Adenosine deaminase prefers a distinct sugar ring conformation for binding and catalysis: Kinetic and structural studies
    • Ford, H., Jr.; Dai, F.; Mu, L.; Siddiqui, M. A.; Nicklaus, M. C.; Anderson, L.; Marquez, V. E.; Barchi, J. J., Jr. Adenosine deaminase prefers a distinct sugar ring conformation for binding and catalysis: Kinetic and structural studies. Biochemistry 2000, 39, 2581-2592.
    • (2000) Biochemistry , vol.39 , pp. 2581-2592
    • Ford H., Jr.1    Dai, F.2    Mu, L.3    Siddiqui, M.A.4    Nicklaus, M.C.5    Anderson, L.6    Marquez, V.E.7    Barchi J.J., Jr.8
  • 44
    • 0011116034 scopus 로고    scopus 로고
    • See the website: http://www.amber.uscf.edu/amber/Questions/fluorine.html.
  • 45
    • 0030937244 scopus 로고    scopus 로고
    • Organic fluorine hardly ever accepts hydrogen bonds
    • Dunitz, J. D.; Taylor, R. Organic fluorine hardly ever accepts hydrogen bonds. Chem. Eur. J. 1997, 3, 89-98.
    • (1997) Chem. Eur. J. , vol.3 , pp. 89-98
    • Dunitz, J.D.1    Taylor, R.2
  • 46
    • 0028003745 scopus 로고
    • Multiple drug effect analysis with confidence interval
    • Belen'kii, S. M.; Schinazi, R. S. Multiple drug effect analysis with confidence interval. Antiviral. Res. 1994, 25, 1-11.0
    • (1994) Antiviral. Res. , vol.25 , pp. 1-11
    • Belen'kii, S.M.1    Schinazi, R.S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.