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Volumn 40, Issue 15, 1997, Pages 2363-2373

Synthesis and anti-HIV-1 activity of a series of 1-alkoxy-5-alkyl-6- (arylthio)uracils

Author keywords

[No Author keywords available]

Indexed keywords

6 [(3,5 DIMETHYLPHENYL)THIO] 1 (3 HYDROXYPROPOXY) 5 ISOPROPYLURACIL; 6 [(3,5 DIMETHYLPHENYL)THIO] 5 ISOPROPYL 1 PROPOXYURACIL; ANTIRETROVIRUS AGENT; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

EID: 0030759473     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9607921     Document Type: Article
Times cited : (34)

References (39)
  • 1
    • 0029011730 scopus 로고
    • Toward Improved Anti-HIV Chemotherapy: Therapeutic Strategies for Intervention with HIV Infections
    • De Clercq, E. Toward Improved Anti-HIV Chemotherapy: Therapeutic Strategies for Intervention with HIV Infections. J. Med. Chem. 1995, 38, 2491-2517.
    • (1995) J. Med. Chem. , vol.38 , pp. 2491-2517
    • De Clercq, E.1
  • 2
    • 0026595037 scopus 로고
    • Antiretrovial Therapy: Reverse Transcriptase Inhibition
    • Connolly, K. J.; Hammer, S. M. Antiretrovial Therapy: Reverse Transcriptase Inhibition. Antimicrob. Agents Chemother. 1992, 36, 245-254.
    • (1992) Antimicrob. Agents Chemother. , vol.36 , pp. 245-254
    • Connolly, K.J.1    Hammer, S.M.2
  • 3
    • 0001707601 scopus 로고
    • 3′-Azido-3′-deoxythymidine (BW A509U): An Antiviral Agent That Inhibits the Infectivity and Cytopathic Effect of Human T-lymphotropic Virus Type III/lymphadenopathy-associated Virus in Vitro
    • Mitsuya, H.; Weinhold, K. J.; Furman, P. A.; St. Clair, M. H.; Nusinoff-Lehrman, S.; Gallo, R. C.; Bolognesi, D. P.; Barry, D. W.; Broder, S. 3′-Azido-3′-deoxythymidine (BW A509U): An Antiviral Agent That Inhibits the Infectivity and Cytopathic Effect of Human T-lymphotropic Virus Type III/lymphadenopathy-associated Virus In Vitro. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 7096-7100.
    • (1985) Proc. Natl. Acad. Sci. U.S.A. , vol.82 , pp. 7096-7100
    • Mitsuya, H.1    Weinhold, K.J.2    Furman, P.A.3    St. Clair, M.H.4    Nusinoff-Lehrman, S.5    Gallo, R.C.6    Bolognesi, D.P.7    Barry, D.W.8    Broder, S.9
  • 6
    • 0001587762 scopus 로고
    • Inhibition of the in vitro Infectivity and Cytopathic Effect of Human T-lymphotropic Virus Type III/lymphadenopathy-associated Virus (HTLV-III/LAV) by 2′,3′-Dideoxynucleosides
    • Mitsuya, H.; Broder, S. Inhibition of the in vitro Infectivity and Cytopathic Effect of Human T-lymphotropic Virus Type III/lymphadenopathy-associated Virus (HTLV-III/LAV) by 2′,3′-Dideoxynucleosides. Proc. Natl. Acad. Sci. U.SA. 1986, 83, 1911-1915.
    • (1986) Proc. Natl. Acad. Sci. U.SA. , vol.83 , pp. 1911-1915
    • Mitsuya, H.1    Broder, S.2
  • 7
    • 0025712101 scopus 로고
    • Salvage Therapy for Zidovudine-intolerant HIV-infected Patients with Alternating and Intermittent Regimens of Zidovudine and Dideoxycytidine
    • Bozzette, S. A.; Richman, D. D. Salvage Therapy for Zidovudine-intolerant HIV-infected Patients with Alternating and Intermittent Regimens of Zidovudine and Dideoxycytidine. Am. J. Med. 1990, 88 (Suppl. 5B), 24S-26S.
    • (1990) Am. J. Med. , vol.88 , Issue.SUPPL. 5B
    • Bozzette, S.A.1    Richman, D.D.2
  • 8
    • 3743065336 scopus 로고
    • Dose Escalating Study of Safety and Efficacy of Dideoxydidehydrothymidine (d4T) for HIV Infection
    • Abst 145
    • Dunkle, L.; Cross, A.; Gugliotti, R.; Martin, R.; Browne, M.; Murray, H. Dose Escalating Study of Safety and Efficacy of Dideoxydidehydrothymidine (d4T) for HIV Infection. Antiviral Res. 1990, Suppl. I, Abst 145.
    • (1990) Antiviral Res. , Issue.SUPPL. I
    • Dunkle, L.1    Cross, A.2    Gugliotti, R.3    Martin, R.4    Browne, M.5    Murray, H.6
  • 13
  • 14
    • 0026771409 scopus 로고
    • 3′-Spironucleosides (TSAO derivatives), a New Class of Specific Human Immunodeficiency Virus Type 1 Inhibitors: Synthesis and Antiviral Activity of 3′-Spiro-5′-[4″-amino-1″,2″-oxathiole-2″, 2″-dioxide]pyrimidine Nucleosides
    • Camarasa, M. J.; Pérez-Pérez, M. J.; San-Félix, A.; Balzarini, J.; De Clercq, E. 3′-Spironucleosides (TSAO derivatives), a New Class of Specific Human Immunodeficiency Virus Type 1 Inhibitors: Synthesis and Antiviral Activity of 3′-Spiro-5′-[4″-amino-1″,2″-oxathiole-2″, 2″-dioxide]pyrimidine Nucleosides. J. Med. Chem. 1992, 35, 2721-2727.
    • (1992) J. Med. Chem. , vol.35 , pp. 2721-2727
    • Camarasa, M.J.1    Pérez-Pérez, M.J.2    San-Félix, A.3    Balzarini, J.4    De Clercq, E.5
  • 15
    • 0027447133 scopus 로고
    • HIV-1-Specific RT Inhibitors: Highly Selective Inhibitors of Human Immunodeficiency Virus Type 1 That Are Specifically Targeted at the Viral Reverse Transcriptase
    • De Clercq, E. HIV-1-Specific RT Inhibitors: Highly Selective Inhibitors of Human Immunodeficiency Virus Type 1 That Are Specifically Targeted at the Viral Reverse Transcriptase. Med. Res. Rev. 1993, 13, 229-258.
    • (1993) Med. Res. Rev. , vol.13 , pp. 229-258
    • De Clercq, E.1
  • 18
    • 0026071537 scopus 로고
    • A New Class of HIV-1-Specific 6-Substituted Acyclouridine Derivatives: Synthesis and Anti-HIV-1 Activity of 5- Or 6-Substituted Analogues of 1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)
    • Tanaka, H.; Baba, M.; Hayakawa, H.; Sakamaki, T.; Miyasaka, T.; Ubasawa, M.; Takashima, H.; Sekiya, K.; Nitta, I.; Shigeta, S.; Walker, R. T.; Balzarini, J.; De Clercq, E. A New Class of HIV-1-Specific 6-Substituted Acyclouridine Derivatives: Synthesis and Anti-HIV-1 Activity of 5- or 6-Substituted Analogues of 1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). J. Med. Chem. 1991, 34, 349-357.
    • (1991) J. Med. Chem. , vol.34 , pp. 349-357
    • Tanaka, H.1    Baba, M.2    Hayakawa, H.3    Sakamaki, T.4    Miyasaka, T.5    Ubasawa, M.6    Takashima, H.7    Sekiya, K.8    Nitta, I.9    Shigeta, S.10    Walker, R.T.11    Balzarini, J.12    De Clercq, E.13
  • 20
    • 0025770237 scopus 로고
    • Specific Anti-HIV-1 "Acyclonucleosides" Which Cannot Be Phosphorylated: Synthesis of Some Deoxy Analogues of 1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine
    • Tanaka, H.; Baba, M.; Saito, S.; Miyasaka, T.; Takashima, H.; Sekiya, K.; Ubasawa, M.; Nitta, I.; Walker, R. T.; Nakashima, H.; De Clercq, E. Specific Anti-HIV-1 "Acyclonucleosides" Which Cannot Be Phosphorylated: Synthesis of Some Deoxy Analogues of 1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine. J. Med. Chem. 1991, 34, 1508-1511.
    • (1991) J. Med. Chem. , vol.34 , pp. 1508-1511
    • Tanaka, H.1    Baba, M.2    Saito, S.3    Miyasaka, T.4    Takashima, H.5    Sekiya, K.6    Ubasawa, M.7    Nitta, I.8    Walker, R.T.9    Nakashima, H.10    De Clercq, E.11
  • 21
    • 0026338152 scopus 로고
    • Activity of Acyclic 6-(Phenylselenenyl)pyrimidine Nucleosides against Human Immunodeficiency Viruses in Primary Lymphocytes
    • Goudgaon, N. M.; Schinazi, R. F. Activity of Acyclic 6-(Phenylselenenyl)pyrimidine Nucleosides against Human Immunodeficiency Viruses in Primary Lymphocytes. J. Med. Chem. 1991, 34, 3305-3309.
    • (1991) J. Med. Chem. , vol.34 , pp. 3305-3309
    • Goudgaon, N.M.1    Schinazi, R.F.2
  • 22
    • 0026543676 scopus 로고
    • Structure-Activity Relationships of 1-[(2-Hydroxyethoxy)-methyl]-6-(phenylthio)thymine (HEPT) Analogues: Effect of Substitutions at the C-6 Phenyl Ring and at the C-5 position on Anti-HIV-1 Activity
    • Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Nitta, I.; Baba, M.; Shigeta, S.; Walker, R. T.; De Clercq, E.; Miyasaka, T. Structure-Activity Relationships of 1-[(2-Hydroxyethoxy)-methyl]-6-(phenylthio)thymine (HEPT) Analogues: Effect of Substitutions at the C-6 Phenyl Ring and at the C-5 position on Anti-HIV-1 Activity. J. Med. Chem. 1992, 35, 337-345.
    • (1992) J. Med. Chem. , vol.35 , pp. 337-345
    • Tanaka, H.1    Takashima, H.2    Ubasawa, M.3    Sekiya, K.4    Nitta, I.5    Baba, M.6    Shigeta, S.7    Walker, R.T.8    De Clercq, E.9    Miyasaka, T.10
  • 23
    • 0027094782 scopus 로고
    • Synthesis and Antiviral Activity of Deoxy Analogs of 1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as Potent and Selective Anti-HIV-1 Agents
    • Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Nitta, I.; Baba, M.; Shigeta, S.; Walker, R. T.; De Clercq, E.; Miyasaka, T. Synthesis and Antiviral Activity of Deoxy Analogs of 1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as Potent and Selective Anti-HIV-1 Agents. J. Med. Chem. 1992, 35, 4713-4719.
    • (1992) J. Med. Chem. , vol.35 , pp. 4713-4719
    • Tanaka, H.1    Takashima, H.2    Ubasawa, M.3    Sekiya, K.4    Nitta, I.5    Baba, M.6    Shigeta, S.7    Walker, R.T.8    De Clercq, E.9    Miyasaka, T.10
  • 24
    • 0029096567 scopus 로고
    • Synthesis and Antiviral Activity of 6-Benzyl Analogs of 1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as Potent and Selective Anti-HIV-1 Agents
    • Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Inouye, N.; Baba, M.; Shigeta, S.; Walker, R. T.; De Clercq, E.; Miyasaka, T. Synthesis and Antiviral Activity of 6-Benzyl Analogs of 1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as Potent and Selective Anti-HIV-1 Agents. J. Med. Chem. 1995, 38, 2860-2865.
    • (1995) J. Med. Chem. , vol.38 , pp. 2860-2865
    • Tanaka, H.1    Takashima, H.2    Ubasawa, M.3    Sekiya, K.4    Inouye, N.5    Baba, M.6    Shigeta, S.7    Walker, R.T.8    De Clercq, E.9    Miyasaka, T.10
  • 25
    • 0029740811 scopus 로고    scopus 로고
    • Synthesis and Anti-HIV-1 Activity of 1,5-Dialkyl-6-(arylselenenyl)uracils and -2-Thiouracils
    • Kim, D.-K.; Kim, H.-T.; Lim, J.; Gam, J.; Kim, Y.-W.; Kim, K. H.; Shin, Y. O. Synthesis and Anti-HIV-1 Activity of 1,5-Dialkyl-6-(arylselenenyl)uracils and -2-Thiouracils. J. Heterocycl. Chem. 1996, 33, 885-894.
    • (1996) J. Heterocycl. Chem. , vol.33 , pp. 885-894
    • Kim, D.-K.1    Kim, H.-T.2    Lim, J.3    Gam, J.4    Kim, Y.-W.5    Kim, K.H.6    Shin, Y.O.7
  • 26
    • 0023835534 scopus 로고
    • Synthesis of 9-(3-Hydroxypropoxy)guanine, a Novel Antiviral Acyclonucleoside
    • Harnden, M. R.; Parkin, A.; Wyatt, P. G. Synthesis of 9-(3-Hydroxypropoxy)guanine, a Novel Antiviral Acyclonucleoside. Tetrahedron Lett. 1988, 29, 701-704.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 701-704
    • Harnden, M.R.1    Parkin, A.2    Wyatt, P.G.3
  • 27
    • 0025058715 scopus 로고
    • Synthesis and Antiviral Activity of 9-Alkoxypurines 1. 9-(3-Hydroxypropoxy)- and 9-[3-Hydroxy-2-(hydroxymethyl)propoxy]purines
    • Harnden, M. R.; Wyatt, P. G.; Boyd, M. R.; Sutton, D. Synthesis and Antiviral Activity of 9-Alkoxypurines 1. 9-(3-Hydroxypropoxy)- and 9-[3-Hydroxy-2-(hydroxymethyl)propoxy]purines. J. Med. Chem. 1990, 33, 187-196.
    • (1990) J. Med. Chem. , vol.33 , pp. 187-196
    • Harnden, M.R.1    Wyatt, P.G.2    Boyd, M.R.3    Sutton, D.4
  • 28
    • 0026023320 scopus 로고
    • Synthesis and Antiviral Activity of 9-Alkoxypurines. 2. 9-(2,3-Dihydroxypropoxy)- and 9-(3,4-Dihydroxybutoxy)-, and 9-(1,4-Dihydroxybut-2-oxy)purines
    • Bailey, S.; Harnden, M. R.; Jarvest, R. L.; Parkin, A.; Boyd, M. R. Synthesis and Antiviral Activity of 9-Alkoxypurines. 2. 9-(2,3-Dihydroxypropoxy)- and 9-(3,4-Dihydroxybutoxy)-, and 9-(1,4-Dihydroxybut-2-oxy)purines. J. Med. Chem. 1991, 34, 57-65.
    • (1991) J. Med. Chem. , vol.34 , pp. 57-65
    • Bailey, S.1    Harnden, M.R.2    Jarvest, R.L.3    Parkin, A.4    Boyd, M.R.5
  • 29
    • 37049075435 scopus 로고
    • Analogues of Acyclonucleoside Diphosphates. The Synthesis of a Series of Diphosphonate Derivatives of Pyrimidines and Purines
    • Parkin, A. Analogues of Acyclonucleoside Diphosphates. The Synthesis of a Series of Diphosphonate Derivatives of Pyrimidines and Purines. J. Chem. Soc., Perkin Trans. 1 1991, 2983-2990.
    • (1991) J. Chem. Soc., Perkin Trans. 1 , pp. 2983-2990
    • Parkin, A.1
  • 30
    • 0026003354 scopus 로고
    • Synthesis of 1-(Phosphonomethoxyalkoxy)pyrimidines, a Novel Series of Acyclonucleotide Analogues
    • Harnden, M. R.; Jennings, L. J.; Parkin, A. Synthesis of 1-(Phosphonomethoxyalkoxy)pyrimidines, a Novel Series of Acyclonucleotide Analogues. Synthesis 1991, 947-950.
    • (1991) Synthesis , pp. 947-950
    • Harnden, M.R.1    Jennings, L.J.2    Parkin, A.3
  • 31
    • 0029114803 scopus 로고
    • A Convenient Approach to the Synthesis of 6-Substituted 1,5-Dialkyluracils and -2-Thiouracils
    • Kim, D.-K.; Kim, Y.-W.; Gam, J.; Lim, J.; Kim, K. H. A Convenient Approach to the Synthesis of 6-Substituted 1,5-Dialkyluracils and -2-Thiouracils. Tetrahedron Lett. 1995, 36, 6257-6260.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6257-6260
    • Kim, D.-K.1    Kim, Y.-W.2    Gam, J.3    Lim, J.4    Kim, K.H.5
  • 32
    • 33846980310 scopus 로고
    • A General, High Yield Synthesis of α-Oxoketene Dithioacetals and O-(1-Alkoxy-2,2-dialkyl)vinyl S-Alkyl Dithiocarbonates from Carboxylic Esters
    • Ali, S. M.; Tanimoto, S. A General, High Yield Synthesis of α-Oxoketene Dithioacetals and O-(1-Alkoxy-2,2-dialkyl)vinyl S-Alkyl Dithiocarbonates from Carboxylic Esters. J. Chem. Soc., Chem. Commun. 1989, 684-685.
    • (1989) J. Chem. Soc., Chem. Commun. , pp. 684-685
    • Ali, S.M.1    Tanimoto, S.2
  • 33
    • 9444272143 scopus 로고
    • General, High Yield Synthesis of α-Oxoketene Dithioacetals and O-(1-Alkoxy-2,2-dialkyl)vinyl N,N-Diisopropylammonium Dithiocarbonates
    • Ali, S. M.; Tanimoto, S. General, High Yield Synthesis of α-Oxoketene Dithioacetals and O-(1-Alkoxy-2,2-dialkyl)vinyl N,N-Diisopropylammonium Dithiocarbonates. Bull. Inst. Chem. Res., Kyoto Univ. 1990, 68, 199-207.
    • (1990) Bull. Inst. Chem. Res., Kyoto Univ. , vol.68 , pp. 199-207
    • Ali, S.M.1    Tanimoto, S.2
  • 34
    • 0020560229 scopus 로고
    • The Reaction of 6-Phenylthiouridine with Sulfur Nucleophiles: A Simple and Regiospecific Preparation of 6-Alkythiouridines and 6-Alkylthiouridylic Acids
    • Tanaka, H.; Iijima, S.; Matsuda, A.; Hayakawa, H.; Miyasaka, T.; Ueda, T. The Reaction of 6-Phenylthiouridine with Sulfur Nucleophiles: A Simple and Regiospecific Preparation of 6-Alkythiouridines and 6-Alkylthiouridylic Acids. Chem. Pharm. Bull. 1983, 31, 1222-1227.
    • (1983) Chem. Pharm. Bull. , vol.31 , pp. 1222-1227
    • Tanaka, H.1    Iijima, S.2    Matsuda, A.3    Hayakawa, H.4    Miyasaka, T.5    Ueda, T.6
  • 35
    • 0024578841 scopus 로고
    • New Soluble-Formazan Assay for HIV-1 Cytopathic Effects: Application to High-Flux Screening of Synthetic and Natural Products for AIDS-Antiviral Activity
    • Weislow, O. S.; Kiser, R.; Fine, D. L.; Bader, J.; Shoemaker, R. H.; Boyd, M. R. New Soluble-Formazan Assay for HIV-1 Cytopathic Effects: Application to High-Flux Screening of Synthetic and Natural Products for AIDS-Antiviral Activity. J. Natl. Cancer Inst. 1989, 81, 577-586.
    • (1989) J. Natl. Cancer Inst. , vol.81 , pp. 577-586
    • Weislow, O.S.1    Kiser, R.2    Fine, D.L.3    Bader, J.4    Shoemaker, R.H.5    Boyd, M.R.6
  • 37
    • 0042041857 scopus 로고
    • Darstellung von O-Alkyl-hydroxy-laminen
    • Theilacker, W.; Ebke, K. Darstellung von O-Alkyl-hydroxy-laminen. Angew. Chem. 1956, 68, 303.
    • (1956) Angew. Chem. , vol.68 , pp. 303
    • Theilacker, W.1    Ebke, K.2


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