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Volumn 55, Issue 16, 2012, Pages 7245-7252

Stereoselective synthesis and antiviral activity of methyl-substituted cycloSal-pronucleotides

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; METHYL GROUP; PHOSPHATE; PRONUCLEOTIDE; STAVUDINE; UNCLASSIFIED DRUG;

EID: 84866914730     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3008085     Document Type: Article
Times cited : (18)

References (41)
  • 1
    • 0028205185 scopus 로고
    • Metabolism and mechanism of antiretroviral action of purine and pyrimidine derivatives
    • Balzarini, J. Metabolism and Mechanism of Antiretroviral Action of Purine and Pyrimidine Derivatives. Pharm. World Sci. 1994, 16, 113-126.
    • (1994) Pharm. World Sci. , vol.16 , pp. 113-126
    • Balzarini, J.1
  • 2
    • 0024592935 scopus 로고
    • Differential Patterns of Intracellular Metabolism of 2', 3'-Didehydro-2', 3'-dideoxythymidine and 3'-Azido-2', 3'-dideoxythymidine, Two Potent Anti-Human Immunodeficiency Virus Compounds
    • Balzarini, J.; Herdewijn, P.; De Clercq, E. Differential Patterns of Intracellular Metabolism of 2', 3'-Didehydro-2', 3'-dideoxythymidine and 3'-Azido-2', 3'-dideoxythymidine, Two Potent Anti-Human Immunodeficiency Virus Compounds. J. Biol. Chem. 1989, 264, 6127-6133.
    • (1989) J. Biol. Chem. , vol.264 , pp. 6127-6133
    • Balzarini, J.1    Herdewijn, P.2    De Clercq, E.3
  • 3
    • 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
  • 4
    • 0036050539 scopus 로고    scopus 로고
    • Strategies in the design of antiviral drugs
    • De Clercq, E. Strategies in the Design of Antiviral Drugs. Nat. Rev. Drug Discovery 2002, 1, 13-25.
    • (2002) Nat. Rev. Drug Discovery , vol.1 , pp. 13-25
    • De Clercq, E.1
  • 5
    • 80054862874 scopus 로고    scopus 로고
    • Application of kinase bypass strategies to nucleoside antivirals
    • Ray, A. S.; Hostetler, K. Y. Application of Kinase Bypass Strategies to Nucleoside Antivirals. Antiviral Res. 2011, 92, 277-291.
    • (2011) Antiviral Res. , vol.92 , pp. 277-291
    • Ray, A.S.1    Hostetler, K.Y.2
  • 6
    • 0033736202 scopus 로고    scopus 로고
    • Pronucleotides: Toward the in vivo delivery of antiviral and anticancer nucleotides
    • Wagner, C. R.; Iyer, V. V.; McIntee, E. J. Pronucleotides: Toward the in Vivo Delivery of Antiviral and Anticancer Nucleotides. Med. Res. Rev. 2000, 20, 417-451.
    • (2000) Med. Res. Rev. , vol.20 , pp. 417-451
    • Wagner, C.R.1    Iyer, V.V.2    McIntee, E.J.3
  • 7
    • 0019276096 scopus 로고
    • Prodrugs and site-specific drug delivery
    • Stella, V. J.; Himmelstein, K. J. Prodrugs and Site-Specific Drug Delivery. J. Med. Chem. 1980, 23, 1275-1282.
    • (1980) J. Med. Chem. , vol.23 , pp. 1275-1282
    • Stella, V.J.1    Himmelstein, K.J.2
  • 8
    • 79251628040 scopus 로고    scopus 로고
    • Diastereoselective Synthesis of cycloSaligenyl-Nucleosyl-Phosphotriesters
    • Rios Morales, E. H; Balzarini, J.; Meier, C. Diastereoselective Synthesis of cycloSaligenyl-Nucleosyl-Phosphotriesters. Chem.-Eur. J. 2011, 17, 1649-1659.
    • (2011) Chem.-Eur. J. , vol.17 , pp. 1649-1659
    • Rios Morales, E.H.1    Balzarini, J.2    Meier, C.3
  • 10
    • 33644778698 scopus 로고    scopus 로고
    • CycloSal-Phosphates as Chemical Trojan Horses for Intracellular Nucleotide and Glycosylmonophosphate Delivery: Chemistry Meets Biology
    • Meier, C. cycloSal-Phosphates as Chemical Trojan Horses for Intracellular Nucleotide and Glycosylmonophosphate Delivery: Chemistry Meets Biology. Eur. J. Org. Chem. 2006, 1081-1102.
    • (2006) Eur. J. Org. Chem. , vol.1 , pp. 081-1102
    • Meier, C.1
  • 11
    • 0003188936 scopus 로고    scopus 로고
    • Nucleotide Delivery from cycloSaligenyl-3′-azido-3′- deoxythymidine Monophosphates (cycloSal-AZTMP)
    • Maaeier, C.; De Clercq, E.; Balzarini, J. Nucleotide Delivery from cycloSaligenyl-3′-azido-3′-deoxythymidine Monophosphates (cycloSal-AZTMP). Eur. J. Org. Chem. 1998, 837-846.
    • (1998) Eur. J. Org. Chem. , vol.8 , pp. 37-846
    • Maaeier, C.1    De Clercq, E.2    Balzarini, J.3
  • 12
    • 54549092707 scopus 로고    scopus 로고
    • Intracellular Trapping of cycloSal-Pronucleotides: Modification of Prodrugs with Amino Acid Esters
    • Jessen, H. J.; Balzarini, J.; Meier, C. Intracellular Trapping of cycloSal-Pronucleotides: Modification of Prodrugs with Amino Acid Esters. J. Med. Chem. 2008, 51, 6592-6598.
    • (2008) J. Med. Chem. , vol.51 , pp. 6592-6598
    • Jessen, H.J.1    Balzarini, J.2    Meier, C.3
  • 13
    • 58149097702 scopus 로고    scopus 로고
    • 5-(1-Acetoxyvinyl)-cycloSaligenyl-2′, 3′-dideoxy-2′, 3′-didehydrothymidine Monophosphates, a Second Type of New, Enzymatically Activated cycloSaligenyl Pronucleotides
    • Gisch, N.; Pertenbreiter, F.; Balzarini, J.; Meier, C. 5-(1-Acetoxyvinyl)-cycloSaligenyl-2′, 3′-dideoxy-2′, 3′-didehydrothymidine Monophosphates, a Second Type of New, Enzymatically Activated cycloSaligenyl Pronucleotides. J. Med. Chem. 2008, 51, 8115-8123.
    • (2008) J. Med. Chem. , vol.51 , pp. 8115-8123
    • Gisch, N.1    Pertenbreiter, F.2    Balzarini, J.3    Meier, C.4
  • 14
    • 66749116603 scopus 로고    scopus 로고
    • Doubly Loaded cycloSaligenyl- Pronucleotides: 5, 5′-Bis- (cycloSaligenyl-2′, 3′-dideoxy-2′, 3′-didehydro- thymidine Monophosphates)
    • Gisch, N.; Balzarini, J.; Meier, C. Doubly Loaded cycloSaligenyl- Pronucleotides: 5, 5′-Bis-(cycloSaligenyl-2′, 3′-dideoxy- 2′, 3′-didehydro-thymidine Monophosphates). J. Med. Chem. 2009, 52, 3464-3473.
    • (2009) J. Med. Chem. , vol.52 , pp. 3464-3473
    • Gisch, N.1    Balzarini, J.2    Meier, C.3
  • 15
    • 33947693161 scopus 로고    scopus 로고
    • Bis-cycloSal-d4T-monophosphates: Drugs That Deliver Two Mole cules of Bioactive Nucleotides
    • Ducho, C.; Gorbig, U.; Jessel, S.; Gisch, N.; Balzarini, J.; Meier, C. Bis-cycloSal-d4T-monophosphates: Drugs That Deliver Two Mole cules of Bioactive Nucleotides. J. Med. Chem. 2007, 50, 1335-1346.
    • (2007) J. Med. Chem. , vol.50 , pp. 1335-1346
    • Ducho, C.1    Gorbig, U.2    Jessel, S.3    Gisch, N.4    Balzarini, J.5    Meier, C.6
  • 16
    • 34147154785 scopus 로고    scopus 로고
    • Enzymatically Activated cycloSal- d4T-monophosphates: The Third Generation of cycloSal-Pronucleo-tides
    • Gisch, N.; Balzarini, J.; Meier, C. Enzymatically Activated cycloSal- d4T-monophosphates: The Third Generation of cycloSal-Pronucleo-tides. J. Med. Chem. 2007, 50, 1658-1667.
    • (2007) J. Med. Chem. , vol.50 , pp. 1658-1667
    • Gisch, N.1    Balzarini, J.2    Meier, C.3
  • 17
    • 0032560234 scopus 로고    scopus 로고
    • CycloSal-2′, 3′-dideoxy-2′, 3′-didehydrothymidine Monophosphate (cycloSal-d4TMP): Synthesis and Antiviral Evaluation of a New d4TMP Delivery System
    • Meier, C.; Lorey, M.; De Clercq, E.; Balzarini, J. cycloSal-2′, 3′-dideoxy-2′, 3′-didehydrothymidine Monophosphate (cycloSal-d4TMP): Synthesis and Antiviral Evaluation of a New d4TMP Delivery System. J. Med. Chem. 1998, 41, 1417-1427.
    • (1998) J. Med. Chem. , vol.41 , pp. 1417-1427
    • Meier, C.1    Lorey, M.2    De Clercq, E.3    Balzarini, J.4
  • 18
    • 56249132165 scopus 로고    scopus 로고
    • Studies on Enzyme-Cleavable Dialkoxymethyl-cycloSaligenyl-2′, 3′-dideoxy-2′, 3′-didehy-drothymidine Monophosphates
    • Gisch, N.; Balzarini, J.; Meier, C. Studies on Enzyme-Cleavable Dialkoxymethyl-cycloSaligenyl-2′, 3′-dideoxy-2′, 3′-didehy-drothymidine Monophosphates. J. Med. Chem. 2008, 51, 6752-6760.
    • (2008) J. Med. Chem. , vol.51 , pp. 6752-6760
    • Gisch, N.1    Balzarini, J.2    Meier, C.3
  • 19
    • 0346732153 scopus 로고    scopus 로고
    • 3, 5-Di-(tert-butyl)-6-fluoro-cycloSal-d4TMP: A Pronucleotide with a Consideraly Improved Masking Group
    • Ducho, C.; Wendicke, S.; Gorbig, U.; Balzarini, J.; Meier, C.3, 5-Di-(tert-butyl)-6-fluoro-cycloSal-d4TMP: A Pronucleotide with a Consideraly Improved Masking Group. Eur. J. Org. Chem. 2003, 4786-4791.
    • (2003) Eur. J. Org. Chem. , pp. 4786-4791
    • Ducho, C.1    Wendicke, S.2    Gorbig, U.3    Balzarini, J.4    Meier, C.5
  • 21
    • 0029975897 scopus 로고    scopus 로고
    • Aryl Phosphoramidate Derivatives of d4T Have Improved Anti-HIV Efficacy in Tissue Culture and May Act by the Generation of a Novel Intracellular Metabolite
    • McGuigan, C.; Cahard, D.; Sheeka, H. M.; De Clercq, E.; Balzarini, J. Aryl Phosphoramidate Derivatives of d4T Have Improved Anti-HIV Efficacy in Tissue Culture and May Act by the Generation of a Novel Intracellular Metabolite. J. Med. Chem. 1996, 39, 1748-1753.
    • (1996) J. Med. Chem. , vol.39 , pp. 1748-1753
    • McGuigan, C.1    Cahard, D.2    Sheeka, H.M.3    De Clercq, E.4    Balzarini, J.5
  • 22
    • 31544483102 scopus 로고    scopus 로고
    • Novel potential anticancer naphthyl phosphoramidates of BVdU: Separation of diastereomers and assignment of the absolute configuration of the phosphorus centre
    • Congiatu, C.; Brancale, A.; Mason, M. D.; Jiang, W. G.; McGuigan, C. Novel Potential Anticancer Naphthyl Phosphoramidates of BVdU: Separation of Diastereomers and Assignment of the Absolute Configuration of the Phosphorus Centre. J. Med. Chem. 2006, 49, 452-455.
    • (2006) J. Med. Chem. , vol.49 , pp. 452-455
    • Congiatu, C.1    Brancale, A.2    Mason, M.D.3    Jiang, W.G.4    McGuigan, C.5
  • 23
    • 78149262004 scopus 로고    scopus 로고
    • Diaster-eoselective Synthesis of Aryloxy Phosphoramidate Prodrugs of 3′-Deoxy-2′, 3′-didehydrothymidine Monophosphate
    • Arbelo Roman, C.; Balzarini, J.; Meier, C. Diaster-eoselective Synthesis of Aryloxy Phosphoramidate Prodrugs of 3′-Deoxy-2′, 3′-didehydrothymidine Monophosphate. J. Med. Chem. 2010, 53, 7675-7681.
    • (2010) J. Med. Chem. , vol.53 , pp. 7675-7681
    • Arbelo Roman, C.1    Balzarini, J.2    Meier, C.3
  • 25
    • 0035901847 scopus 로고    scopus 로고
    • Separation of Individual Antiviral Nucleotide Prodrugs from Synthetic Mixtures Using Cross-Reactivity of a Molecularly Imprinted Stationary Phase
    • Allender, C. J.; Brain, K. R.; Ballatore, C.; Cahard, D.; Siddiqui, A.; McGuigan, C. Separation of Individual Antiviral Nucleotide Prodrugs from Synthetic Mixtures Using Cross-Reactivity of a Molecularly Imprinted Stationary Phase. Anal. Chim. Acta 2001, 435, 107-113.
    • (2001) Anal. Chim. Acta , vol.435 , pp. 107-113
    • Allender, C.J.1    Brain, K.R.2    Ballatore, C.3    Cahard, D.4    Siddiqui, A.5    McGuigan, C.6
  • 27
    • 19444368441 scopus 로고    scopus 로고
    • Stereoselective synthesis of nucleoside monophosphate hepdirect prodrugs
    • Reddy, K. R.; Boyer, S. H.; Erion, M. D. Stereoselective Synthesis of Nucleoside Monophosphate HepDirect Prodrugs. Tetrahedron Lett. 2005, 46, 4321-4324.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 4321-4324
    • Reddy, K.R.1    Boyer, S.H.2    Erion, M.D.3
  • 31
    • 0037193087 scopus 로고    scopus 로고
    • 3-Phosphono-2-(N-cyanoimino)thiazolidine derivatives, new phos-phorylating agents for alcohols
    • Maezaki, N.; Furusawa, A.; Hirose, Y.; Uchida, S.; Tanaka, T. 3-Phosphono-2-(N-cyanoimino)thiazolidine Derivatives, New Phos-phorylating Agents for Alcohols. Tetrahedron 2002, 58, 3493-3498.
    • (2002) Tetrahedron , vol.58 , pp. 3493-3498
    • Maezaki, N.1    Furusawa, A.2    Hirose, Y.3    Uchida, S.4    Tanaka, T.5
  • 32
    • 0347624284 scopus 로고    scopus 로고
    • Azido-Neonicotinoids as Candidate Photoaffinity Probes for Insect Nicotinic Acetylcholine Receptors [1]
    • Maienfisch, P.; Haettenschwiler, J.; Rindlisbacher, A.; Decock, A.; Wellmann, H.; Kayser, H. Azido-Neonicotinoids as Candidate Photoaffinity Probes for Insect Nicotinic Acetylcholine Receptors [1]. Chimia 2003, 57, 710-714.
    • (2003) Chimia , vol.57 , pp. 710-714
    • Maienfisch, P.1    Haettenschwiler, J.2    Rindlisbacher, A.3    Decock, A.4    Wellmann, H.5    Kayser, H.6
  • 33
    • 23044491533 scopus 로고    scopus 로고
    • Phosphorylation of alcohols with n-phosphoryl oxazolidinones employing copper(II) triflate catalysis
    • Jones, S.; Smanmoo, C. Phosphorylation of Alcohols with N-Phosphoryl Oxazolidinones Employing Copper(II) Triflate Catalysis. Org. Lett. 2005, 7, 3271-3274.
    • (2005) Org. Lett. , vol.7 , pp. 3271-3274
    • Jones, S.1    Smanmoo, C.2
  • 35
    • 84858738652 scopus 로고    scopus 로고
    • Radiolabeled Cyclosaligenyl Monophosphates of 5-Iodo-2′- deoxyuridine, 5-Iodo-3′-fluoro-2′, 3′-dideoxyuridine, and 3′-Fluorothymidine for Molecular Radiotherapy of Cancer: Synthesis and Biological Evaluation
    • Kortylewicz, Z. P.; Kimura, Y.; Inoue, K.; Mack, E.; Baranowska- Kortylewicz, J. Radiolabeled Cyclosaligenyl Monophosphates of 5-Iodo-2′-deoxyuridine, 5-Iodo-3′-fluoro-2′, 3′-dideoxyuridine, and 3′-Fluorothymidine for Molecular Radiotherapy of Cancer: Synthesis and Biological Evaluation. J. Med. Chem. 2012, 55, 2649-2671.
    • (2012) J. Med. Chem. , vol.55 , pp. 2649-2671
    • Kortylewicz, Z.P.1    Kimura, Y.2    Inoue, K.3    MacK, E.4    Baranowska-Kortylewicz, J.5
  • 38
    • 0001015246 scopus 로고
    • Stereochemistry of nucleophilic displacement reactions at the thiophos-phoryl centre-I
    • Michalski, J.; Mikolajczyk, M. Stereochemistry of Nucleophilic Displacement Reactions at the Thiophos-phoryl Centre-I*. Tetrahedron 1966, 22, 3055-3059.
    • (1966) Tetrahedron , vol.22 , pp. 3055-3059
    • Michalski, J.1    Mikolajczyk, M.2
  • 39
    • 49949148673 scopus 로고
    • Stereochemistry of nucleophilic displacement reactions at the thiophosphoryl centre-II
    • Mikolajczyk, M. Stereochemistry of Nucleophilic Displacement Reactions at the Thiophosphoryl Centre-II. Tetrahedron 1967, 23, 1543-1549.
    • (1967) Tetrahedron , vol.23 , pp. 1543-1549
    • Mikolajczyk, M.1
  • 40
    • 37049064758 scopus 로고
    • Stereochemistry of the reaction of O-ethyl ethylphosphonothioic acid with phosphorus pentachloride
    • Michalski, J.; Mikolajczyk, M. Stereochemistry of the Reaction of O-Ethyl Ethylphosphonothioic Acid with Phosphorus Pentachloride. Chem. Commun. 1965, 35-36.
    • (1965) Chem. Commun. , vol.3 , pp. 5-36
    • Michalski, J.1    Mikolajczyk, M.2
  • 41
    • 0037832471 scopus 로고    scopus 로고
    • Aryl-Substituted and Benzo-Annulated cycloSal-Derivatives of 2′, 3′-Dideoxy-2′, 3′-didehydrothymidine Monophosphate: Correlation of Structure, Hydrolysis Properties and Anti-HIV Activity
    • Ducho, C.; Balzarini, J.; Naesens, L.; De Clercq, E.; Meier, C. Aryl-Substituted and Benzo-Annulated cycloSal-Derivatives of 2′, 3′-Dideoxy-2′, 3′-didehydrothymidine Monophosphate: Correlation of Structure, Hydrolysis Properties and Anti-HIV Activity. Antiviral Chem. Chemother. 2002, 13, 129-141.
    • (2002) Antiviral Chem. Chemother. , vol.13 , pp. 129-141
    • Ducho, C.1    Balzarini, J.2    Naesens, L.3    De Clercq, E.4    Meier, C.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.