Synthesis of C-oxetanosyl-thiazole and its carbocyclic analog nucleosides as potential chemotherapeutic agents

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 16, 1996, Pages 1897-1900

  Kikuchi, Yoshiko ^a   Nishiyama, Shigeru ^a   Yamamura, Shosuke ^a   Kato, Kuniki ^b   Fujiwara, Sari ^a   Umezawa, Kazuo ^a   Terada, Yukimasa ^c  

^a KEIO UNIVERSITY   (Japan)

^b NIPPON KAYAKU CO LTD   (Japan)

^c MEIJO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 [2,3 BIS(HYDROXYMETHYL)CYCLOBUTYL] 4 THIAZOLECARBOXAMIDE; ANTINEOPLASTIC AGENT; NERVE GROWTH FACTOR; NUCLEOSIDE DERIVATIVE; TIAZOFURIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CELL DIFFERENTIATION; COMPUTER SIMULATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG DESIGN; DRUG SYNTHESIS; NONHUMAN; RAT;

ANIMALIA; LEUCISCUS IDUS;

EID: 0030594969     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00340-X     Document Type: Article

References (22)

1. 1. Goldstein, B. M.; Leary, J. F.; Farley, B. A.; Marquez, V. E.; Rowley, P. T. Blood 1991, 78, 593-598.
2. 2. Parandoosh, Z.; Rubalcava, B.; Matsumoto, S. S.; Jolley, W. B.; Robins, R. K. Life Sci. 1990, 46, 315-320.
3. 3. Kharbanda, S. M.; Sherman, M. L.; Springgs, D. R.; Kufe, D. W. Cancer Res. 1988, 48, 5965-5968.
4. 4. Srivastava, P. C.; Pickerling, M. V.; Allen, L. B.; Streeter, D. G.; Campbell, M. T.; Witkowski, J. T.; Sidwell, R. W.; Robins, R. K. J. Med. Chem. 1977, 20, 256-262.
5. 5. Srivastava, P. C.; Robins, R. K. J. Med. Chem. 1983, 26, 445-448.
6. 6. Jayaram, H. N.; Smith, A. L.; Glazer, R. I.; Johns, D. G.; Cooney, D. A. Biochem. Pharmacol. 1982, 31, 3839-3845. Jayaram, H. N.; Ahluwaria, G. S.; Dion, R. L.; Gebeyehu, G.; Marquez, V. E.; Kelley, J. A.; Robins, R. K.; Cooney, D. A.; Johns, D. G. Biochem. Pharmacol. 1983, 32, 2633-2636.
7. 6. Jayaram, H. N.; Smith, A. L.; Glazer, R. I.; Johns, D. G.; Cooney, D. A. Biochem. Pharmacol. 1982, 31, 3839-3845. Jayaram, H. N.; Ahluwaria, G. S.; Dion, R. L.; Gebeyehu, G.; Marquez, V. E.; Kelley, J. A.; Robins, R. K.; Cooney, D. A.; Johns, D. G. Biochem. Pharmacol. 1983, 32, 2633-2636.
8. 7. Kuttan, R.; Robins, R. K.; Saunders, P. P. Biochem. Biophys. Res. Commun. 1982, 107, 862-868. Cooney, D. A.; Jayaram, H. N.; Gebeyehu, G.; Betts, C. R.; Kelley, J. A.; Marquez, V. E.; Johns, D. G. Biochem. Pharmacol. 1982, 31, 2133-2136. Li, H.; Hallows, W. H.; Punzi, J. S.; Marquez, V. E.; Carrell, H. L.; Pankiewicz, K. W.; Watanabe, K. A.; Goldstein, B. M. Biochemistry 1994, 33, 23-32.
9. 7. Kuttan, R.; Robins, R. K.; Saunders, P. P. Biochem. Biophys. Res. Commun. 1982, 107, 862-868. Cooney, D. A.; Jayaram, H. N.; Gebeyehu, G.; Betts, C. R.; Kelley, J. A.; Marquez, V. E.; Johns, D. G. Biochem. Pharmacol. 1982, 31, 2133-2136. Li, H.; Hallows, W. H.; Punzi, J. S.; Marquez, V. E.; Carrell, H. L.; Pankiewicz, K. W.; Watanabe, K. A.; Goldstein, B. M. Biochemistry 1994, 33, 23-32.
10. 7. Kuttan, R.; Robins, R. K.; Saunders, P. P. Biochem. Biophys. Res. Commun. 1982, 107, 862-868. Cooney, D. A.; Jayaram, H. N.; Gebeyehu, G.; Betts, C. R.; Kelley, J. A.; Marquez, V. E.; Johns, D. G. Biochem. Pharmacol. 1982, 31, 2133-2136. Li, H.; Hallows, W. H.; Punzi, J. S.; Marquez, V. E.; Carrell, H. L.; Pankiewicz, K. W.; Watanabe, K. A.; Goldstein, B. M. Biochemistry 1994, 33, 23-32.
11. 8. Yeh, Y. A.; Olah, E.; Wendel, J. J.; Sledge, G. W. Jr.; Weber, G. Proc. Amer. Assoc. Cancer Res. 1994, 35: Abst. 1978.
12. 9. Burling, F. T.; Goldstein, B. M. J. Am. Chem. Soc. 1992, 114, 2313-2320.
13. 10. This calculation was carried out using the same program (MOPAC-MNDO) as cited in the reference 9.
14. 11. Witty, D. R.; Fleet, G. W. J.; Choi, S.; Vogt, K.; Wilson, F. X.; Wang, Y.; Storer, R.; Myers, P. L.; Wallis, C. J. Tetrahedron Lett. 1990, 47, 6927-6930.
15. 12. Izawa, T.; Nakayama, K.; Nishiyama, S.; Yamamura, S.; Kato, K.; Takita, T. J. Chem. Soc., Perkin Trans. 1, 1992, 3003-3004.
16. 13. Ichikawa, Y.; Narita, A.; Shiozawa, A.; Hayashi, Y.; Narasaka, K. J. Chem. Soc., Chem. Commun. 1989, 1919-1921. Ahmad, S. Tetrahedron Lett. 1991, 32, 6997-7000.
17. 13. Ichikawa, Y.; Narita, A.; Shiozawa, A.; Hayashi, Y.; Narasaka, K. J. Chem. Soc., Chem. Commun. 1989, 1919-1921. Ahmad, S. Tetrahedron Lett. 1991, 32, 6997-7000.
18. 14. Several attempts of the substitution reaction of the stable mesylate of the alcohol 14 with cyanide ion under various conditions were unsuccessful.
19. ++1), found 245.0583.
20. 2S, found 242.0715.
21. 17. Hagag, N.; Halegoura, S.; Viola, M. Nature 1986, 319, 680.
22. 18. Evaluation of compounds 3 and 4 against HSV-1 and HSV-2 in Vero cells by a plaque reduction assay at concentrations up to 100 μg/ml revealed these compounds to be devoid of antiviral activity and cytotoxicity.