Collect. Czech. Chem. Commun.
2000, 65, 1698-1712
https://doi.org/10.1135/cccc20001698
Synthesis of Acyclic Nucleoside and Nucleotide Analogs Derived from 6-Amino-7H-purine-8(9H)-thione and 8-(Methylsulfanyl)adenine
Zlatko Janeba*, Antonín Holý and Milena Masojídková
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
References
1a. Antiviral Res. 1987, 8, 261.
< E., Baba M., Pauwels R., Balzarini J., Rosenberg I., Holý A.: https://doi.org/10.1016/S0166-3542(87)80004-9>
1b. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 332.
< J., Maesens L., Herdewijn P., Rosenberg I., Holý A., Pauwels R., Baba M., John D. G., De Clercq E.: https://doi.org/10.1073/pnas.86.1.332>
2. Collect. Czech. Chem. Commun. 2000, 65, 1126.
< Z., Holý A., Masojídková M.: https://doi.org/10.1135/cccc20001126>
3a. J. Pharm. Sci. 1967, 56, 955.
< B. R., Hendrickson J. L.: https://doi.org/10.1002/jps.2600560806>
3b. J. Med. Chem. 1968, 11, 652.
< B. R., Kozma J. A.: https://doi.org/10.1021/jm00310a004>
4a. Saneyoshi M. (Seikagaku Kogyo Co., Ltd): Japan 67 25,910, 09 Dec. 1967; Chem. Abstr. 1968, 69, 52455.
4b. Saneyoshi M. (Seikagaku Kogyo Co., Ltd): Japan 67 24,914, 29 Nov. 1967; Chem. Abstr. 1968, 69, 59284.
5. Eur. J. Med. Chem. 1994, 29, 287.
< E., Bani M., Favara D., Gobetti M., Lombroso M., Magnetti S., Olgiati V., Palladino M., Tonon G. C.: https://doi.org/10.1016/0223-5234(94)90098-1>
6. J. Biol. Chem. 1951, 505.
G. B., Hitchings G. H., Vanderwerf H.:
7. Ann. N. Y. Acad. Sci. 1954, 60, 183.
< G. H., Rhoads C. P.: https://doi.org/10.1111/j.1749-6632.1954.tb40008.x>
8a. J. Chem. Soc. 1954, 2060.
< A., Brown D. J.: https://doi.org/10.1039/jr9540002060>
8b. J. Am. Chem. Soc. 1958, 80, 6671.
< R. K.: https://doi.org/10.1021/ja01557a051>
9. J. Am. Chem. Soc. 1964, 86, 1242.
< R. E., Robins R. K.: https://doi.org/10.1021/ja01060a057>
10a. J. Med. Chem. 1985, 28, 1194.
< T. S., Cheng J. C., Ishiguro K., Sartorelli A. C.: https://doi.org/10.1021/jm00147a012>
10b. Tetrahedron Lett. 1991, 32, 4823.
< J., Burr L., Chen R.: https://doi.org/10.1016/S0040-4039(00)93470-1>
10c. J. Org. Chem. 1967, 32, 3042.
< M., Muneyama K.: https://doi.org/10.1021/jo01285a023>
11. Bioorg. Med. Chem. Lett. 2000, 10, 2387.
< X., Cooperman B. S.: https://doi.org/10.1016/S0960-894X(00)00481-9>
12. J. Org. Chem. 2000, 65, 249.
< S., Gautier-Luneau I., Fontecave M., Décout J.-L.: https://doi.org/10.1021/jo9908492>
13. Janeba Z., Holý A. in: Collection Symposium Series (A. Holý and M. Hocek, Eds), Vol. 2, p. 260. Institute if Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague 1999.
14. J. Med. Chem. 1999, 42, 1625.
< E., Camaioni E., Jang S.-Y., Kim Y.-Ch., Cristalli G., Herdewijn P., Secrist J. A., Tiwari K. N., Mohanram A., Harden T. K., Boyer J. L., Jacobson K. A.: https://doi.org/10.1021/jm980657j>
15a. Tetrahedron Lett. 1994, 35, 4989.
< A., Décout J.-L., Lhomme J.: https://doi.org/10.1016/S0040-4039(00)73300-4>
15b. Tetrahedron Lett. 1997, 38, 8687.
< E., Renard A., Defrancq E., Lhomme J.: https://doi.org/10.1016/S0040-4039(97)10335-5>
16. Collect. Czech. Chem. Commun. 1993, 58, 649.
< A.: https://doi.org/10.1135/cccc19930649>
17. Collect. Czech. Chem. Commun. 1996, 61, 442.
< Z., Holý A., Votavová H., Masojídková M.: https://doi.org/10.1135/cccc19960442>
18a. Chem. Pharm. Bull. 1968, 16, 1151.
< M., Kaneko M., Sagai M.: https://doi.org/10.1248/cpb.16.1151>
18b. Acc. Chem. Res. 1969, 2, 47.
< M.: https://doi.org/10.1021/ar50014a003>
18c. Chem. Listy 2000, 94, 355.
Z.:
19a. J. Chem. Soc. 1951, 2952.
< V. M., Todd A. R., Zussman J.: https://doi.org/10.1039/jr9510002952>
19b. Tetrahedron 1970, 26, 5675.
< M., Kaneko M., Okano R.: https://doi.org/10.1016/0040-4020(70)80003-5>
19c. Tetrahedron Lett. 1974, 6, 497.
< M., Tanaka S.: https://doi.org/10.1016/S0040-4039(01)82254-1>
19d. Tetrahedron 1980, 36, 3509.
< T., Minamoto K., Itoh H.: https://doi.org/10.1016/0040-4020(80)88046-X>
20. Synthesis 1981, 1.
< O.: https://doi.org/10.1055/s-1981-29317>
21a. Nucleosides Nucleotides 1993, 12, 941.
< J.-W., Kuo Ch.-Ch., Chang M.-J., Liu L.-T.: https://doi.org/10.1080/07328319308018564>
21b. Collect. Czech. Chem. Commun. (Special Issue) 1996, 61, S116.
< Z., Holý A.: https://doi.org/10.1135/cccc1996s116>
21c. Nucleosides Nucleotides 1998, 17, 869.
< K., Tsuji T., Muraoka M.: https://doi.org/10.1080/07328319808003459>
22. Collect. Czech. Chem. Commun. 1986, 51, 459.
< A., Kohoutová J., Merta A., Votruba I.: https://doi.org/10.1135/cccc19860459>
23a. Tetrahedron 1968, 24, 3489.
< M., Tada H., Kaneko M.: https://doi.org/10.1016/S0040-4020(01)92646-8>
23b. J. Am. Chem. Soc. 1968, 90, 497.
< M., Kaneko M.: https://doi.org/10.1021/ja01004a053>
23c. Tetrahedron Lett. 1968, 4707.
< M., Kaneko M., Nakahara Y.: https://doi.org/10.1016/S0040-4039(00)89912-8>
24. J. Am. Chem. Soc. 1965, 87, 606.
< M., Tada H.: https://doi.org/10.1021/ja01081a038>
25. Chem. Pharm. Bull. 1971, 19, 1381.
< M., Kaneko M., Nakahara Y., Yamada S., Uesugi S.: https://doi.org/10.1248/cpb.19.1381>