Acyclic nucleotide analogs derived from 8-azapurines: Synthesis and antiviral activity

Journal of Medicinal Chemistry

Volumn 39, Issue 20, 1996, Pages 4073-4088

  Holý, Antonín ^a   Dvořáková, Hana ^a   Jindřich, Jindřich ^a,c   Masojídková, Milena ^a   Buděšínský, Miloš ^a   Balzarini, Jan ^b   Andrei, Graciella ^b   De Clercq, Erik ^b  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^c CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

8 AZAPURINE DERIVATIVE; ANTIVIRUS AGENT; CESIUM;

ALKYLATION; ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOMEGALOVIRUS; DRUG SYNTHESIS; GLYCOSYLATION; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; MOLONEY MURINE SARCOMA ONCOVIRUS; NONHUMAN; VARICELLA ZOSTER VIRUS;

3T3 CELLS; ADENINE; ANIMALS; ANTIVIRAL AGENTS; CELL TRANSFORMATION, VIRAL; CYTOMEGALOVIRUS; CYTOPATHOGENIC EFFECT, VIRAL; GUANINE; HERPESVIRUS 1, HUMAN; HERPESVIRUS 2, HUMAN; HERPESVIRUS 3, HUMAN; HIV-1; HIV-2; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MICE, INBRED C3H; MOLECULAR STRUCTURE; PURINES; SARCOMA VIRUSES, MURINE;

EID: 0029796606     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960314q     Document Type: Article

References (88)

1. (a) Holý, A.; Votruba, I.; Merta, A.; C̀erný, J.; Veselý, J.; Vlach, J.; Šedivá, K.; Rosenberg, I.; Otmar, M.; Hřebabecký, H.; Trávníček, M.; Vonka, V.; Snoeck, R.; De Clercq, E. Acyclic Nucleotide Analogs: Synthesis, Antiviral Activity and Inhibition Effects on Some Cellular and Virus Encoded Enzymes in vitro. Antiviral Res. 1990, 13, 295-312.
2. (b) De Clercq, E. Broadspectrum Anti-DNA Virus and Anti-retrovirus Activity of Phosphonylmethoxyalkyl Purines and Pyrimidines. Biochem. Pharmacol. 1991, 42, 963-972.
3. (c) Holý, A. Isopolar Phosphorus-Modified Nucleotide Analogues. In Advances in Antiviral Drug Design, 1st ed.; De Clercq, E., Ed.; JAI Press, Inc.: Greenwich, CT, 1994; pp 179-232.
4. (a) 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, 23, 464-467.
5. (b) De Clercq, E.; Sakuma, T.; Baba, M.; Pauwels, R.; Balzarini, J.; Rosenberg, I.; Holý, A. Antiviral Activity of Phosphonylmethoxyalkyl Derivatives of Purines and Pyrimidines. Antiviral Res. 1987, 8, 261-272.
6. (c) Baba, M.; Konno, K.; Shigeta, S.; De Clercq, E. In vitro Activity of (S)-9-(3-Hydroxy-2-phosphonylmethoxypropyl)adenine Against Newly Isolated Clinical Varicella-Zoster Virus Strains. Eur. J. Clin. Microbiol. Infect. Dis. 1987, 6, 158-160.
7. Terry, B. J.; Mazina, K. E.; Tuomari, A. V.; Haffey, M. L.; Hagen, M.; Feldman, A.; Slusarchyk, W. A.; Young, M. G.; Zahler, R.; Field, A. K. Broad-spectrum antiviral activity of the acyclic guanosine phosphonate (R,S)-HPMPG. Antiviral Res. 1988, 10, 235-251.
8. (a) Balzarini, J.; Naesens, L.; Herdewijn, P.; Rosenberg, I.; Holý, A.; Pauwels, R.; Baba, M.; Johns, D. G.; De Clercq, E. Marked in vivo Antiretrovirus Activity of 9-(2-Phosphonylmethoxyethyl)-adenine, A Selective Antihuman Immunodeficiency Virus Agent. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 332-336.
9. (b) Gangemi, J. D.; Cozens, R. M.; De Clercq, E.; Balzarini, J.; Hochkeppel, H. K. 9-(2-Phosphonylmethoxyethyl)adenine in the Treatment of Murine Acquired Immunodeficiency Disease and Opportunistic Herpes Simplex Virus Infections. Antimicrob. Agents Chemother. 1989, 33, 1864-1868.
10. (c) Balzarini, J.; Hao, Z.; Herdewijn, P.; Johns, D. G.; De Clercq, E. Intracellular Metabolism and Mechanism of Antiretrovirus Action of 9-(2-Phosphonylmethoxy-ethyl)adenine, A Potent Antihuman Immunodeficiency Virus Compound. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 1499-1503.
11. (d) Balzarini, J.; Perno, C. F.; Schols, D.; De Clercq, E. Activity of Acyclic Nucleoside Phosphonate Analogues Against Human Immunodeficiency Virus in Monocyte/ Macrophages and Peripheral Blood Lymphocytes. Biochem. Biophys. Res. Commun. 1991, 178, 329-335.
12. (e) Naesens, L.; Neyts, J.; Balzarini, J.; Holý, A.; Rosenberg, I.; De Clercq, E. Efficacy of Oral 9-(2-Phosphonylmethoxyethyl)-2,6-diaminopurine (PMEDAP) in the Treatment of Retrovirus and Cytomegalovirus Infections in Mice. J. Med. Virol. 1993, 39, 167-172.
13. (f) Naesens, L.; Balzarini, J.; De Clercq, E. Therapeutic Potential of PMEA as an Antiviral Drug. Rev. Med. Virol. 1994, 4, 147-159.
14. (a) Naesens, L.; Balzarini, J.; Rosenberg, I.; Holý, A.; De Clercq, E. 9-(2-Phosphonylmethoxyethyl)-2,6-diaminopurine (PMEDAP): A Novel Agent with Antihuman Immunodeficiency Virus Activity in vitro and Potent Anti-Moloney Murine Sarcoma Virus Activity in vivo. Eur. J. Clin. Microbiol. Infect. Dis. 1989, 8, 1043-1047.
15. (b) Balzarini, J.; Naesens, L.; Slachmuylders, J.; Niphuis, H.; Rosenberg, I.; Holý, A.; Schellekens, H.; De Clercq, E. 9-(2-Phosphonylmethoxyethyl)adenine (PMEA) Effectively Inhibits Simian Immunodeficiency Virus (SIV) Infection in Rhesus Monkeys. AIDS 1991, 5, 21-28.
16. (c) Thormar, H.; Balzarini, J.; Holý, A.; Jindřich, J.; Rosenberg, I.; Debyser, Z.; Desmyter, J.; De Clercq, E. Inhibition of Visna Virus Replication by 2′,3′-Dideoxynucleosides and Acyclic Nucleoside Phosphonate Analogs. Antimicrob. Agents Chemother. 1993, 37, 2540-2544.
17. (d) Hoover, E. A.; Ebner, J. P.; Zeidner, N. S.; Mullins, J. I. Early Therapy of Feline Leukemia Virus Infection (FeLV,FAIDS) with 9-(2-Phosphonylmethoxyethyl)adenine (PMEA). Antiviral Res. 1991, 16, 77-92.
18. (e) Egberink, H.; Borst, M.; Niphuis, H.; Balzarini, J.; Neu, H.; Schellekens, H.; De Clercq, E.; Horzinek, M.; Koolen, M. Suppression of Feline Immunodeficiency Virus Infection in vivo by 9-(2-Phosphonomethoxyethyl)adenine. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 3087-3091.
19. (a) Gong, Y. F.; Marshall, D. R.; Srinivas, R. V.; Fridland, A. Susceptibilities of Zidovudine-Resistant Variants of Human Immunodeficiency Virus Type 1 to Inhibition by Acyclic Nucleoside Phosphonates. Antimicrob. Agents Chemother. 1994, 38, 1683-1687.
20. (b) Cundy, K. C.; Barditch-Crovo, P. A.; Walker, R. E.; Collier, A. C.; Ebeling, D.; Toole, J.; Jaffe, H. S. Clinical Pharmacokinetics of Adefovir in Human Immunodeficiency Virus Type 1 Infected Patients. Antimicrob. Agents Chemother. 1995, 39, 2401-2405.
21. Starrett, J. E.; Tortolani, D. R.; Russell, J.; Hitchcock, M. J. M.; Whiterock, V.; Martin, J. C.; Mansuri, M. M. Synthesis, Oral Bioavailability Determination, and in vitro Evaluation of Prodrugs of the Antiviral Agent 9-[2-(Phosphonomethoxy)ethyl]-adenine (PMEA). J. Med. Chem. 1994, 37, 1857-1864.
22. (b) Naesens, L.; Neyts, J.; Balzarini, J.; Bischofberger, N.; De Clercq, E. In vivo Antiretroviral Efficacy of Oral Bis(POM)-PMEA, the Bis(pivaloyloxymethyl) Prodrug of 9-(2-Phosphonylmethoxyethyl)adenine (PMEA). Nucleosides Nucleotides 1995,14, 767-770.
23. (a) Heijtink, R. A.; De Wilde, G. A.; Kruining, J.; Berk, L.; Balzarini, J.; De Clercq, E.; Holy, A.; Schalm, S. W. Inhibitory Effect of 9-(2-Phosphonylmethoxyethyl)adenine (PMEA) on Human and Duck Hepatitis B Virus Infection. Antivir. Res. 1993, 21, 141-153.
24. (b) Heijtink, R. A.; Kruining, J.; De Wilde, G. A.; Balzarini, J.; De Clercq, E.; Schalm, S. W. Inhibitory Effects of Acyclic Nucleoside Phosphonates on Human Hepatitis B Virus and Duck Hepatitis B Virus Infections in Tissue Culture. Antimicrob. Agents Chemother. 1994, 38, 2180-2182.
25. (c) Balzarini, J.; Kruining, J.; Heijtink, R.; De Clercq, E. Comparative Antiretrovirus and Antihepadnavirus Activity of Three Different Classes of Nucleoside Phosphonate Derivatives. Antivir. Chem. Chemother. 1994, 5, 360-365.
26. (d) Tsai, C. C.; Follis, K. E.; Sabo, A.; Grant, R.; Bischofberger, N. Efficacy of 9-(2-Phosphonylmethoxyethyl)adenine Treatment against Chronic Simian Immunodeficiency Virus Infection in Macaques. J. Infect. Dis. 1995, 171, 1338-1343.
27. Kreider, J. W.; Balogh, K.; Olson, R. O.; Martin, J. C. Treatment of Latent Rabbit and Human Papillomavirus Infections with 9-(2-Phosphonylmethoxyethyl)guanine (PMEG). Antiviral Res. 1990, 14, 51-58.
28. (a) Rose, W. C.; Crosswell, A. R.; Bronson, J. J.; Martin, J. C. In vivo Antitumor Activity of 9-[(2-Phosphonylmethoxy)ethyl]guanine and Related Phosphonate Nucleotide Analogues. J. Natl. Cancer Inst. 1990, 82, 510-512.
29. (b) Otová, B.; Sladká, M.; Blažek, K.; Schramlová, J.; Votruba, I.; Holý, A. Cytostatic Effect of 9-(2-Phosphonomethoxyethyl)adenine (PMEA). 2. Lymphoblastic Leukemia in Sprague Dawley Rats. Folia Biol. Prague. 1993, 39, 142.
30. (c) Otová, B.; Křenová, D.; Zídek, Z.; Holý, A.; Votruba, I.; Křen, V. Cytostatic Effect of 9-(2-Phosphonomethoxyethyl)adenine (PMEA). 3. Rat and Mouse Carcinomas and Sarcomas. Folia Biol. Prague. 1993, 39, 311-314.
31. Balzarini, J.; Holý, A.; Jindřich, J.; Dvořáková, H.; Hao, Z.; Snoeck, R.; Herdewijn, P.; Johns, D. G.; De Clercq, E. 9-[(2RS)-3-Fluoro-2-phosphonylmethoxypropyl] Derivatives of Purines: a New Class of Highly Selective Antiretroviral Agents in vitro and in vivo. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 4961-4965.
32. (a) Holý, A.; Masojídková, M. Synthesis of Enantiomeric N-(2-Phosphonomethoxypropyl) Derivatives of Purine and Pyrimidine bases. 1. The Stepwise Approach. Collect. Czech. Chem. Commun. 1995, 60, 1196-1212.
33. (b) Holý, A.; Dvořáková, H.; Masojídková, M. Synthesis of Enantiomeric N-(2-Phosphonomethoxypropyl) Derivatives of Heterocyclic Bases. 2. Synthon Approach. Collect. Czech. Chem. Commun. 1995, 60, 1390-1409.
34. (a) Balzarini, J.; Holý, A.; Jindřich, J.; Naesens, L.; Snoeck, R.; Schols, D.; De Clercq, E. Differential Antiretrovirus Effects of the (S) and (R)-Enantiomers of Acyclic Nucleoside Phosphonates. Potent and Selective in vitro and in vivo Antiretrovirus Activity of the (A)-9-(2-Phosphonomethoxypropyl) Derivatives of Heterocyclic Bases. Antimicrob. Agents Chemother. 1993, 37, 332-338.
35. (b) Vahlenkamp, T. W.; Deronde, A.; Balzarini, J.; Naesens, L.; De Clercq, E.; Vaneijk, M. J. T.; Horzinek, M. C.; Egberink, H. F. (R)-9-(2-phosphonylmethoxypropyl)-2,6-diaminopurine is a potent inhibitor of feline immunodeficiency virus infection. Antimicrob. Agents Chemother. 1995, 39, 746-749.
36. (c) Balzarini, J; Aquaro S, Perno CF, Witvrouw, M; Holý, A; De Clercq, E.: Anti-human Immunodeficiency Virus Activity of the (R)-Enantiomer of 9-(2-Phosphonylmethoxypropyl)adenine [(R)-PMPA] and 9-(2-Phosphonylmethoxypropyl)-2,6-diaminopurine [(R)-PMPDAP] in Different Human Cell Systems. Biochem. Biophys. Res. Commun. 1996, 219, 337-341.
37. Tsai, C. C.; Follis, K. E.; Sabo, A.; Beck, T. W.; Grant, R. F.; Bischofberger, N.; Benveniste, R. E.; Black, R. Prevention of SIV Infection in Macaques by (R)-9-(2-Phosphonylmethoxypropyl)-adenine. Science 1995, 270, 1197-1199.
38. (a) Votruba, I.; Bernaerts, R.; Sakuma, T.; De Clercq, E.; Merta, A.; Rosenberg, I.; Holý, A, Intracellular Phosphorylation of Broad-Spectrum anti-DNA Virus Agent (S)-9-(3-Hydroxy-2-phosphonylmethoxypropyl)adenine and Inhibition of Viral DNA Synthesis. Mol. Pharmacol. 1987, 32, 524-529.
39. (b) Merta, A.; Veselý, J.; Votruba, I.; Rosenberg, I.; Holý, A. Phosphorylation of Acyclic Nucleotide Analogues HPMPA and PMEA in L1210 Mouse Leukemic Cell Extracts. Neoplasma 1990, 37, 111-120.
40. (c) Balzarini, J.; De Clercq, E. 5-Phosphoribosyl-1-pyrophosphate Synthetase Converts the Acyclic Nucleoside Phosphonates 9-(3-Hydroxy-2-phosphonylmethoxypropyl)adenine and 9-(2-Phosphonylmethoxyethyl)adenine Directly to Their Antivirally Active Diphosphate Derivatives. J. Biol. Chem. 1991, 266, 8686-8689.
41. (d) Merta, A.; Votruba, I.; Jindřich, J.; Holý, A.; Cihlář, T.; Rosenberg, I.; Otmar, M.; Hervé, T. Y. Phosphorylation of 9-(2-Phosphonomethoxyethyl)adenine and 9-(S)-(3-Hydroxy-2-phosphonomethoxypropyl)adenine by AMP(dAMP) Kinase from L1210 Cells. Biochem. Pharmacol. 1992, 44, 2067-2077.
42. (e) Aduma, P.; Connelly, M. C.; Srinivas, R. V.; Fridland, A. Metabolic Diversity and Antiviral Activities of Acyclic Nucleoside Phosphonates. Mol. Pharmacol. 1995, 47, 816-822.
43. Šedivá, K.; Ananiev, A. V.; Votruba, I.; Holý, A.; Rosenberg, I. Inhibition of Purine Nucleoside Phosphorylase by Phosphonylmethyl Analogues of Nucleotides. Int. J. Purine Pyrim. Res. 1991, 2, 35-40.
44. Dvořáková, H.; Holy, A.; Alexander, P. Synthesis and Biological Effects of 9-(3-Hydroxy-2- phosphonomethoxypropyl) Derivatives of Deazapurine Bases. Collect. Czech. Chem. Commun. 1993, 58, 1403-1418.
45. Dvořáková, H.; Holý, A.; Snoeck, R.; Balzarini, J.; De Clercq, E. Acyclic nucleoside and nucleotide analogues derived from 1-deaza- and 3-deazaadenine. Collect. Czech. Chem. Commun. Special Issue No. 1 1990, 55, 113-116.
46. De Vries, E.; Stam, J. G.; Franssen, F. F.; Nieuwenhuijs, H.; Chavalitshewinkoon, P.; De Clercq, E.; Overdulve, J. P.; Van der Vliet, P. C. Inhibition of the Growth of Plasmodium falciparum and Plasmodium berghei by the DNA Polymerase Inhibitor HPMPA. Mol. Biochem. Parasitol. 1991, 47, 43-50.
47. (a) Robins, R. K. J. Med.Chem. 1964, 7, 186.
48. (b) Allan, P. W.; Bennett, L. L. Proc. Am. Assoc. Cancer Res. 1970, 11, 2.
49. (c) Bennett, L. L.; Vail, M. H.; Allan, P. H.; Laster, W. R. Cancer Res. 1973, 33, 465.
50. (d) Montgomery, J. A. Nucleosides, Nucleotides and their Biological Applications; Academic Press: New York, 1983; pp 19-46.
51. (e) Montgomery, J. A.; Elliott, R. D.; Thomas, H. J. The Synthesis and Evaluation of Azapurine Nucleosides As Cytotoxic Agents. Ann. N.Y. Acad. Sci. 1975, 255, 292-305.
52. (f) Smith, C. W.; Sidwell, R. W.; Robins, R. K.; Tolman, R. L. J. Med. Chem. 1972, 15, 883.
53. (g) Bennett, L. L.; Shannon, W. M.; Allan, P. W.; Arnett G. Ann. N.Y. Acad. Sci. 1975, 255, 342.
54. (h) Bennett, L. L.; Jr., Allan, P. W. Metabolism and Metabolic Effects of 8-Azainosine and 8-Azaadenosine. Cancer Res. 1976, 36, 3917-3923.
55. (i) Montgomery, J. A.; Elliott, R. D.; Thomas, H. J. The Synthesis and Evaluation of Azapurine Nucleosides As Cytotoxic Agents. Ann. N.Y. Acad. Sci. 1975, 255, 292-305.
56. Marr, J. J.; Berens, R. L.; Cohn, N. K.; Nelson, D. J.; Nichol, C. A. Biological Action of Inosine Analogs in Leishmania and Trypanosoma spp. Antimicrob. Agents Chemother. 1984, 25, 292-295.
57. Hocková, D.; Masojídková, M.; Buděšínský, M.; Holý, A. Acyclic Nucleoside and Nucleotide Analogs Derived from 2-Azaadenine. Collect. Czech. Chem. Commun. 1995, 60, 224-236.
58. (a)Dvořáková H.; Holý, A.; Masojídková, M.; Votruba, I.; Balzarini, J.; Snoeck, R.; De Clercq, E. Synthesis and Antiviral Activity of Acyclic Nucleoside and Nucleotide Derivatives of 8-Azaadenine. Collect. Czech. Chem. Commun. Special Issue No. 1 1993, 58, 253-255.
59. (b) Holý, A.; Dvořáková, H.; Hocková, D.; Balzarini, J.; Snoeck, R.; De Clercq, E. Antiviral Activity of Acyclic Nucleoside Phosphonate Analogues Derived From Azapurine Bases. Antiviral Res. 1994, 24, Suppl. I, 365.
60. (c) Holý, A.; Dvořaková, H. Acyclic Nucleotide Analogues and Related Compounds. Nucleosides Nucleotides 1995, 14, 695-702.
61. Franchetti, P.; Abu-Sheikha, G.; Cappellacci, L.; Messina, L.; Grifantini, M.; Loi, A. G.; Demontis, A.; Spiga, M. G.; La Colla, P. 8-Aza Analogues of PMEA and PMEG: Synthesis and in vitro Anti-HIV Activity. Nucleosides Nucleotides 1994, 13, 1707-1719.
62. Revankar, G. R.; Robins, R. K. The Synthesis and Chemistry of Heterocyclic Analogues of Purine Nucleosides and Nucleotides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York 1991; Part 2, pp 297-306.
63. (a) Seela, F.; Mersmann, K. 8-Azaguanine 2′,3′-Didexyribonucleosides: Glycosylation of the 5-amino-7-methoxy-3h-1,2,3-triazolo(4,5d]pyrimidinyl Anion with 2,3-dideoxy-D- Glyceropentofuranosyl Chloride. Helv. Chim. Acta. 1993, 76, 2184-2193.
64. (b) Seela, F.; Lampe, S. 8-Aza-2′-deoxyguanosine and Related 1,2,3-Triazolo[4,5d]pyrimidine 2′-Deoxyribofuranosides. Helv. Chim. Acta 1993, 76, 2388-2397.
65. Barili, P. L.; Biagi, G.; Giorgi, I.; Livi, O.; Scartoni, V. A Method for the Synthesis of Racemic and Optically Active 2-substituted 9-(2′,3′-Dihydroxypropyl)-8-azahypoxanthines and 8-Azaadenines. J. Heterocycl. Chem. 1991, 28, 1351-1355.
66. Franchetti, P.; Abu-Sheikha, G.; Cappellacci, L.; Grifantini, M.; Demontis, A.; Piras, G.; Loi, A. G.; La Colla, P. Synthesis and Antiviral Activity of 8-Aza Analogues of Chiral [2-(Phosphonomethoxy)propyl]guanines. J. Med. Chem. 1995, 38, 4007-4013.
67. Dvořáková, H.; Holy, A.; Votruba, I.; Masojídková, M. Synthesis and Biological Effects of Acyclic Analogs of Deazapurine Nucleosides. Collect. Czech. Chem. Commun. 1993, 58, 629-648.
68. (a) De Clercq, E.; Holý, A. Antiviral Activity of Aliphatic Nucleoside Analogues: Structure-Function Relationship. J. Med. Chem. 1979, 22, 510-513.
69. (b) Holy, A. Biologically stable Nucleoside and Nucleotide Analogs: Present State and Perspectives. Chem. Scr. 1986, 26, 83-89.
70. Alexander, P.; Holý, A. General Method for the Preparation of N-(3-Hydroxy-2-phosphonomethoxypropyl) Derivatives of Heterocyclic Bases. Collect. Czech. Chem. Commun. 1993, 58, 1151-1163.
71. Holý, A.; Rosenberg, I.; Dvořáková, H. Synthesis of N-(2-Phosphonylmethoxyethyl) Derivatives of Heterocyclic Bases. Collect. Czech. Chem. Commun. 1989, 54, 2190-2210.
72. Jindřich, J.; Holý, A; Dvořáková, H. Synthesis of N-(3-Fluoro-2-phosphonomethoxypropyl) (FPMP) Derivatives of Heterocyclic Bases. Collect. Czech. Chem. Commun. 1993, 58, 1645-1667.
73. Holý, A.; Dvořáková, H.; Jindřich, J. Antiviral Acyclic Nucleotide Analogues. In Antibiotics and Antiviral Compounds, 1st ed.; Krohn, K.; Kirst, H. A.; Maag, H.; Eds.; Verlag Chemie: Weinheim/New York, 1993.
74. Holý, A. Syntheses of Enantiomeric N-(3-Hydroxy-2-phosphonomethoxypropyl) Derivatives of Purine and Pyrimidine Bases. Collect. Czech. Chem. Commun. 1993, 58, 649-674.
75. Žemlička, J.; Chládek, S.; Holý, A.; Smrt, J. Synthesis of Some Diribonucleoside Phosphates using the N-Dimethylaminomethylene Derivatives of 2′,3′-Ethoxymethylene Ribonucleosides. Collect. Czech. Chem. Commun. 1966, 31, 3198-3212.
76. Kazimierczuk, Z.; Binding, U.; Seela, F. Synthesis of 8-Aza-2′-deoxyadenosine and Related 7-Amino-3H-1,2,3-triazolo[4,5-d]-pyrimidine 2′-Deoxyribofuranosides: Stereoselective Glycosylation via the Nucleobase Anion. Helv. Chim. Acta 1989, 72, 1527-1536.
77. 13C Magnetic Resonance Signal of Sugars: Signal Assignment Studies. Can. J. Chem. 1974, 52, 458-463.
78. 13C Spectra of Stachyose and its Subunits. J. Chem. Soc., Perkin Trans. 2 1984, 481-488.
79. (c) Christofifes, J. C.; Davies, B. D. Secondary Isotope Multiplet NMR Spectroscopy of Partially Labeled Entities. Carbon-13 SIMPLE NMR Spectra of Carbohydrates. J. Am. Chem. Soc. 1983, 105, 5099-5105.
80. 13C NMR of Polyols with Partially Deuterated Hydroxyls. 2. Effects of Cis-Trans Isomerism in Cyclic Vicinal Diol Systems. J. Am. Chem. Soc. 1984, 106, 2461-2462.
81. (e) Reuben, J. Isotopic Multiplets in the Proton-Decoupled Carbon-13 NMR Spectra of Carbohydrates with Partially Deuterated Hydrogens. J. Am. Chem. Soc. 1983, 105, 3711-3713.
82. 13C NMR. 1.Resonance Reassignment of Mono- and Disaccharides. J. Am. Chem. Soc. 1979, 101, 1265-1274.
83. Hocková, D.; Masojídková, M; Buděšínský, M.; Holý, A. Acyclic Nucleoside and Nucleotide Analogues Derived from 2-Azaadenine. Collect. Czech. Chem. Commun. 1995, 60, 224-236.
84. Patt, S. L.; Shoolery, J. N. Attached Proton Test for Carbon-13 NMR. J. Magn. Reson. 1982, 46, 535-539.
85. Brechbühler, H.; Büchi, H.; Schreiber, J.; Eschenmoser, A. Die Reaktion von Carbonsäuren mit Acetalen des N,N-Dimethylformamids: eine Veresterungsmethode. Helv. Chim. Acta 1965, 48, 1746-1771.
86. Holý, A.; Ivanova, G. S. Aliphatic Analogues of Nucleotides: Synthesis and Affinity towards Nucleases. Nucleic Acids Res. 1974, 1, 19-34.
87. De Clercq, E.; Descamps, J.; Verhelst, G.; Walker, R. T.; Jones, A. S.; Torrence, P. F.; Shugar, D. Comparative Efficacy of Antiherpes Drugs Against Different Strains of Herpes Simplex Virus. J. Infect. Dis. 1980, 141, 563-574.
88. De Clercq, E.; Merigan, T. C. Moloney Sarcoma Virus Induced Tumors in Mice: Inhibition or Stimulation by (poly rI):poly(rC). Proc. Soc. Exp. Biol. Med. 1971, 137, 590-594.