Synthesis, antiproliferative and antiviral activity of imidazo[4,5- d]isothiazole nucleosides as 5:5 fused analogs of nebularine and 6- methylpurine ribonucleoside

Journal of Medicinal Chemistry

Volumn 40, Issue 5, 1997, Pages 771-784

  Swayze, Eric E ^a   Drach, John C ^b   Wotring, Linda L ^b   Townsend, Leroy B ^b  

^a ISIS PHARMACEUTICALS   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYL 6 BETA D RIBOFURANOSYLIMIDAZO[4,5 D]ISOTHIAZOLE; 4 (2 DEOXY BETA D ERYTHROPENTOFURANOSYL) 5 [(PHENYLMETHYL)THIO]IMIDAZO[4,5 D]ISOTHIAZOLE; 4 BETA D ARABINOFURANOSYL 5 [(PHENYLMETHYL)THIO]IMIDAZO[4,5 D]ISOTHIAZOLE; 5 (BENZYLTHIO) 6 (2 DEOXY BETA D RIBOFURANOSYL)IMIDAZO[4,5 D]ISOTHIAZOLE; IMIDAZOLE DERIVATIVE; NEBULARINE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; VIRUS INFECTION; VIRUS REPLICATION;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CELLS, CULTURED; CYTOMEGALOVIRUS; HUMANS; IMIDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MOLECULAR STRUCTURE; PURINE NUCLEOSIDES; PURINES; RIBONUCLEOSIDES; SIMPLEXVIRUS; THIAZOLES; THIONUCLEOSIDES;

EID: 0031055902     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960605z     Document Type: Article

References (43)

1. Brown, G. B.; Weliky, V. S. The Synthesis of 9-β-D-Ribofuranosylpurine and the Identity of Nebularine. J. Biol. Chem. 1953, 204, 1019-1024.
2. Giner-Sorolla, A.; Medrek, L.; Bendich, A. Synthesis and Biological Activity of 9-β-D-Ribofuranosyl-6-hydroxylaminopurine. J. Med. Chem. 1966, 9, 143-144.
3. Elion, G. B.; Burgi, E.; Hitchings, G. H. Studies on Condensed Pyrimidine Systems. IX. The Synthesis of Some 6-Substituted Purines. J. Am. Chem. Soc. 1952, 74, 411-414.
4. Schabel, F. M., Jr.; Montgomery, J. A.; Skipper, H. E.; Laster, W. R., Jr.; Thomson, J. R. Experimental Evaluation of Potential Anticancer Agents I. Quantitative Therapeutic Evaluation of Certain Purine Analogs. Cancer Res. 1961, 21, 690-699.
5. Montgomery, J. A.; Schabel, F. M., Jr.; Skipper, H. E. Experimental Evaluation of Potential Anticancer Agents IX. The Ribonucleosides and Ribonucleotides of Two Purine Antagonists. Cancer Res. 1962, 22, 504-509.
6. Bennett, L. L., Jr.; Vail, M. H.; Chumley, S.; Montgomery, J. A. Activity of Adenosine Analogs Against a Cell Culture Line Resistant to 2-Fluoroadenine. Biochem. Pharmacol. 1966, 15, 1719-1728.
7. Montgomery, J. A.; Clayton, S. J.; Fitzgibbon, W. E., Jr. The Ribonucleosides of 4-Aminopyrazolo[3,4-d]pyrimidine. J. Heterocycl. Chem. 1964, 1, 215-216.
8. Mizuno, Y.; Ikehara, M.; Watanabe, K. A.; Suzaki, S.; Itoh, T. Synthetic Studies of Potential Antimetabolites. IX. The Anomeric Configuration of Tubercidin. J. Org. Chem. 1963, 28, 3329-3331.
9. Tolman, R. L.; Robins, R. K.; Townsend, L. B. Pyrrolopyrimidine Nucleosides III. The Total Synthesis of Toyocamycin, Sangivamycin, Tubercidin, and Related Derivatives. J. Am. Chem. Soc. 1969, 91, 2102-2108.
10. Townsend, L. B.; Drach, J. C.; Wotring, L. L.; Vittori, S.; Pudlo, J. S.; Swayze, E. E.; Gupta, P.; Maruyama, T.; Saxena, N.; Coleman, L. A.; Westerman, A. C.; Spurr, J.; Nassiri, M. R.; Turk, S. R.; Krawczyk, S. H. Design, Synthesis, and Studies on the Structure Activity Relationships of Certain Pyrrolo[2,3-d]-pyrimidine Nucleosides and Structurally Related Analogs as Potential Antineoplastic and Antiviral Agents. Il Farmaco 1991, 46, 113-139.
11. Namikoshi, M.; Carmichael, W. W.; Sakai, R.; Jares-Erijman, E. A.; Kaup, A. M.; Rinehart, K. L. 9-Deazaadenosine and Its 5′-α-D-Glucopyranoside Isolated from the Cyanobacterium anabaena affinis Strain VS-1. J. Am. Chem. Soc. 1993, 115, 2504-2505.
12. Koyama, G.; Maeda, K.; Umezawa, H.; Iitaka, Y. The Structural Studies of Formycin and Formycin B. Tetrahedron Lett. 1966, 597-602.
13. Robins, R. K.; Townsend, L. B.; Cassidy, F.; Gerster, J. F.; Lewis, A. F.; Miller, R. L. Structure of the Nucleoside Antibiotics Formycin, Formycin B and Laurusin (1). J. Heterocycl. Chem. 1966, 3, 110-114.
14. Shimada, N; Yagisawa, N.; Naganawa, H.; Takita, T.; Hamada, M.; Takeuchi, T.; Umezawa, H. Oxanosine, a Novel Nucleoside From Actinomycetes. J. Antibiot. 1981, 34, 1216-1218.
15. Parkanyi, C. Recent Progress in the Quantum Chemistry of Organic Sulfur Compounds. Mech. React. Sulfur Compd. 1969, 4, 69-94.
16. Chwang, T. L.; Nemec, J.; Welch, A. D. Synthesis and Characterization of 5-Amino-2-(β-D-ribofuranosyl)-1,2,4-thiadiazoline-3-one, a Sulfur-Containing Analog of Cytidine. J. Carbohydr. Nucleosides Nucleotides 1980, 7, 159-166.
17. Gordon, M. P.; Weliky, V. S.; Brown, G. B. A Study of the Action of Acid and Alkali on Certain Purines and Purine Nucleosides. J. Am. Chem. Soc. 1957, 79, 3245-3250.
18. Montgomery, J. A.; Hewson, K. Analogs of 6-Methyl-9-β-D-ribofuranosylpurine. J. Med. Chem. 1968, 11, 48-52.
19. (a) Swayze, E. E. The Synthesis of Several Members of the New Imidazo[4,5-d]isothiazole Ring System: Novel 5:5 Fused Analogs of Purines and Purine Nucleosides. Ph.D. Thesis, 1994, The University of Michigan, Ann Arbor, MI.
20. (b) Swayze, E. E.; Townsend, L. B. The Synthesis of Substituted Imidazo[4,5-d]-isothiazoles via the Ring Annulation of Isothiazole Diamines: An Investigation of the Chemical, Physical, and Biological Properties of Several Novel 5:5 Fused Analogs of the Purine Ring System. J. Org. Chem. 1995, 60, 6309-6317.
21. Srivastava, P. C.; Robins, R. K.; Meyer, R. B. Synthesis and Properties of Purine Nucleosides and Nucleotides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1988; Vol. 1, pp 113-281.
22. 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; Vol. 2, pp 161-398.
23. Swayze, E. E.; Townsend, L. B. The Synthesis of Several Imidazo[4,5-d]isothiazoles; Derivatives of a New Ring System. 206th American Chemical Society National Meeting (Org #351), August 22-27, 1993, Chicago, IL.
24. Swayze, E. E.; Townsend, L. B. The Synthesis of Several Imidazo[4,5-d]isothiazoles; Derivatives of a New Ring System. J. Heterocycl. Chem. 1993, 30, 1379-1383.
25. Kazimierczuk, Z.; Cottam, H. B.; Revankar, G. R.; Robins, R. K. Synthesis of 2′-Deoxyadenosine, and Related 2′-Deoxynucleosides via a Novel Direct Stereospecific Sodium Salt Glycosylation Procedure. J. Am. Chem. Soc. 1984, 106, 6379-6382.
26. Hoffer, M. α-Thymidin. Chem. Ber. 1960, 93, 2777-2781.
27. Chenon, M.-T.; Pugmire, R. J.; Grant, D. M.; Panzica, R. P.; Townsend, L. B. Carbon-13 Magnetic Resonance. XXV. A Basic Set of Parameters for the Investigation of Tautomerism in Purines Established from Carbon-13 Magnetic Resonance Studies Using Certain Purines and Pyrrolo[2,3-d]pyrimidines. J. Am. Chem. Soc. 1975, 97, 4627-4636.
28. Townsend, L. B. Nuclear Magnetic Resonance Spectroscopy in the Study of Nucleic Acid Components and Certain Related Derivatives. In Synthetic Procedures in Nucleic Acid Chemistry; Zorbach, W. W., Tipson, R. S., Eds.; John Wiley & Sons: New York, 1972; Vol. 2, pp 323-340.
29. Bhattacharya, A. K.; Ness, R. K.; Fletcher, H. G., Jr. 2-Deoxy-D-erythro-pentose. IX. Some Relationships Among the Rotations of Acylated Aldopentoses, Aldopentosyl Halides, and Anhydropentitols. J. Org. Chem. 1963, 28, 428-435.
30. Ramasamy, K.; Imamura, N.; Robins, R. K.; Revankar, G. R. A Facile and Improved Synthesis of Tubercidin and Certain Related Pyrrolo[2,3-d]pyrimidine Nucleosides by the Stereospecific Sodium Salt Glycosylation Procedure. J. Heterocycl. Chem. 1988, 25, 1893-1898.
31. Ramasamy, K.; Robins, R. K.; Revankar, G. R. Direct Synthesis of Pyrrole Nucleosides by the Stereospecific Sodium Salt Glycosylation Procedure. J. Heterocycl. Chem. 1987, 24, 863-868.
32. Glaudemans, C. P. J.; Fletcher, H. G., Jr. Syntheses with Partially Benzylated Sugars. III. A Simple Pathway to a "cis-Nucleoside," 9-β-D-Arabinofuranosyladenine (Spongoadenosine). J. Org. Chem. 1963, 28, 3004-3006.
33. Pudlo, J. S.; Townsend, L. B. A New and Novel Approach Towards the Synthesis of 3′-Deoxy-3′-hydroxymethyl Ribofuranosides. Tetrahedron Lett. 1990, 22, 3101-3104.
34. Vorbruggen, H.; Krolikiewicz, K.; Bennua, B. Nucleoside Synthesis with Trimethylsilyl Triflate and Perchlorate as Catalysts. Chem. Ber. 1981, 114, 1234-1255.
35. Stevens, J. D.; Ness, R. K.; Fletcher, H. G., Jr. Syntheses with Partially Benzylated Sugars. XI. Studies on the Synthesis of the Anomeric 5,6-Dimethyl-1-D-ribofuranosylbenzimidazoles (Ribazoles). Comparison of the Condensation of 2,3,5-Tri-O-benzoyl-D-ribofuranosyl Bromide and 2,3,5-Tri-O-benzyl-D-ribofuranosyl Chloride with 5,6-Dimethylbenzimidazole. J. Org. Chem. 1968, 33, 1806-1810.
36. Tapiero, C.; Imbach, J.-L. The Determination of Anomeric Configuration of D-Ribofuranosyl Nucleosides by Proton Magnetic Resonance Spectroscopy. In Nucleic Acid Chemistry. Improved and New Synthetic Procedures, Methods, and Techniques; Townsend, L. B., Tipson, R. S., Eds.; John Wiley & Sons: New York, 1978; Part 2, pp 1055-1059.
37. Baker, B. R. In Ciba Foundation Symposium on the Chemistry and Biology of Purines; Wolstenholme, G. E., O'Connor, C. M., Eds.; Little, Brown and Co.: Boston, 1957; p 120.
38. Wotring, L. L.; Townsend, L. B. Study of the Cytotoxicity and Metabolism of 4-amino-3-carboxamido-1-(β-D-ribofuranosyl)pyrazolo[3,4-d]pyrimidine Using Inhibitors of Adenosine Kinase and Adenosine Deaminase. Cancer Res. 1979, 39, 3018-3023.
39. Meade, E. A.; Wotring, L. L.; Drach, J. C.; Townsend, L. B. Synthesis, Antiproliferative, and Antiviral Activity of 4-Amino-1-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyridazin-7(6H)-one and Related Derivatives. J. Med. Chem. 1993, 36, 3834-3842.
40. Turk, S. R.; Shipman, C., Jr.; Nassiri, M. R.; Genzingler, G.; Krawczyk, S. H.; Townsend, L. B.; Drach, J. C. Pyrrolo[2,3-d]-pyrimidine Nucleosides as Inhibitors of Human Cytomegalovirus. Antimicrob. Agents Chemother. 1987, 31, 544-550.
41. Prichard, M. N.; Turk, S. R.; Coleman, L. A.; Engelhardt, S. L.; Shipman, C., Jr.; Drach, J. C. A Microtiter Virus Yield Reduction Assay for the Evaluation of Antiviral Compounds Against Human Cytomegalovirus and Herpes Simplex Virus, J. Virol. Methods 1990, 28, 101-106.
42. Prichard, M. N.; Shipman, C., Jr. A Three-dimensional Model to Analyze Drug-drug Interactions. Antiviral Res. 1990, 14, 181-206.
43. Prichard, M. N.; Prichard, L. E.; Baguley, W. A.; Nassiri, M. R.; Shipman, C., Jr. Three-dimensional Analysis of the Synergistic Cytotoxicity of Ganciclovir and Zidovudine. Antimicrob. Agents Chemother. 1991, 35, 1060-1065.