Collect. Czech. Chem. Commun. 2003, 68, 711-743
https://doi.org/10.1135/cccc20030711

Synthesis of N4-Alkyl-5-azacytidines and Their Base-Pairing with Carbamoylguanidines - A Contribution to Explanation of the Mutagenicity of 2'-Deoxy-5-azacytidine

Alois Pískala*, Naeem B. Hanna, Milena Masojídková, Miroslav Otmar, Pavel Fiedler and Karel Ubik

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic

References

1. Pískala A., Šorm F.: Collect. Czech. Chem. Commun. 1964, 29, 2060. <https://doi.org/10.1135/cccc19642060>
2. Šorm F., Pískala A., Čihák A., Veselý J.: Experientia 1964, 20, 202. <https://doi.org/10.1007/BF02135399>
3. Hanka L. J., Evans J. S., Mason D. J., Dietz A.: Antimicrob. Agents Chemother. 1966, 619.
4. Bergy M. E., Herr R. R.: Antimicrob. Agents Chemother. 1966, 625.
5. Pískala A., Šorm F. in: Nucleic Acid Chemistry (L. B. Townsend and R. S.Tipson, Eds), Part 1, p. 435. Wiley, New York 1978.
6. Pliml J., Šorm F.: Collect. Czech. Chem. Commun. 1964, 29, 2576. <https://doi.org/10.1135/cccc19642576>
7. Šorm F., Pískala A.: Neth. 6 414 959; Chem. Abstr. 1966, 64, 2154.
8. Pískala A., Šorm F. in: Nucleic Acid Chemistry (L. B. Townsend and R. S. Tipson, Eds), Part 1, p. 443. Wiley, New York 1978.
9. Glover A. B., Leyland-Jones B. R., Chun H. G., Davies B., Hoth D. F.: Cancer Treat. Rep. 1987, 71, 737.
10. Momparler R. L., Momparler L. F., Samson J.: Leuk. Res. 1984, 8, 1043. <https://doi.org/10.1016/0145-2126(84)90059-6>
11. Momparler R. L., Onetto-Pothier N., Momparler L. F.: Leuk. Res. 1990, 14, 755. <https://doi.org/10.1016/0145-2126(90)90068-K>
12. Kantarjian H. M., O’Brien S. M., Keating M., Beran M., Estey E., Giralt S., Kornblau S., Rios M. B., de Vos D., Talpaz M.: Leukemia 1997, 11, 1617. <https://doi.org/10.1038/sj.leu.2400796>
13. Kantarjian H. M., O’Brien S. M., Estey E., Giralt S., Beran M., Rios M. B., Keating M., de Vos D., Talpas M.: Leukemia 1997, 11(Suppl. 1), 35.
14. Momparler R. L., Bouffard D. Y., Momparler L. F., Dionne J., Belanger K., Ayoub J.: Anticancer Drugs 1997, 8, 358. <https://doi.org/10.1097/00001813-199704000-00008>
15. Thibault A., Figg W. D., Bergan R. C., Lush R. M., Myers C. E., Tompkins A., Reed E., Samid D.: Tumori 1998, 84, 87. <https://doi.org/10.1177/030089169808400120>
16. Veselý J., Čihák A.: Pharmacol. Ther. 1978, 2, 813.
17. Jones P. A.: Cell 1985, 40, 485. <https://doi.org/10.1016/0092-8674(85)90192-8>
18. Momparler R. L., Côté S., Eliopoulos N.: Leukemia 1997, 11(Suppl. 1), 1.
19. Bender C. M., Pao M. M., Jones P. A.: Cancer Res. 1998, 58, 95.
20. Jones P. A., Baylin S. B.: Nat. Rev. Genet. 2002, 3, 415. <https://doi.org/10.1038/nrg962>
21. Santi D. V., Garrett C. E., Barr P. J.: Cell 1983, 33, 9. <https://doi.org/10.1016/0092-8674(83)90327-6>
22. Santi D. V., Norment A., Garrett C. E.: Proc. Natl. Acad Sci. U.S.A. 1984, 81, 6993. <https://doi.org/10.1073/pnas.81.22.6993>
23. Piťhová P., Piťha J., Pískala A., Šorm F.: Collect. Czech. Chem. Commun. 1965, 30, 2801. <https://doi.org/10.1135/cccc19652801>
24. Lin K.-T., Momparler R. L., Rivard G. E.: J. Pharm. Sci. 1981, 70, 1228. <https://doi.org/10.1002/jps.2600701112>
25. Momparler R. L.: Pharmacol. Ther. 1985, 30, 287. <https://doi.org/10.1016/0163-7258(85)90053-1>
26. Hanna N. B., Masojídková M., Pískala A.: Collect. Czech. Chem. Commun. 1998, 63, 713. <https://doi.org/10.1135/cccc19980713>
27. Pískala A., Čihák A., Hanna N. B., Škutchan J. in: Proceedings of the Third FECHEM Conference on Heterocycles in Bio-Organic Chemistry, Balatonfűred, May 20–23, 1984 (H. C. van der Plas, L. Ötvöss and M. Simonyi, Eds). Akadémiai Kiadó, Budapest 1984.
28. Šorm F., Pískala A.: Ger. Offen. 1 922 702; Chem. Abstr. 1970, 72, 79427.
29. Pískala A.: Collect. Czech. Chem. Commun. 1967, 32, 3966. <https://doi.org/10.1135/cccc19673966>
30. Mertes M. P., Pískala A., Škutchan J., Veselý J.: Nucleic Acids Res. Symp. Ser. 1984, 14, 237.
31. Pískala A., Česneková B., Veselý J.: Nucleic Acids Res. Symp. Ser. 1987, 18, 57.
32. Mele A., Panzeri W., Selva A.: J. Mass Spectrom. 1997, 32, 807. <https://doi.org/10.1002/(SICI)1096-9888(199708)32:8<807::AID-JMS534>3.0.CO;2-J>
33. Mele A., Panzeri W., Selva A.: Eur. Mass Spectrom. 1997, 3, 347. <https://doi.org/10.1255/ejms.166>
34. Mathusudanan K. P., Katti S. B., Dwivedi A. K.: J. Mass Spectrom. 1998, 33, 1017. <https://doi.org/10.1002/(SICI)1096-9888(1998100)33:10<1017::AID-JMS721>3.0.CO;2-Q>
35. Alexander D., Holý P., Fiedler P., Havlas Z., Závada J.: Collect. Czech. Chem. Commun. 1996, 61, 1464. <https://doi.org/10.1135/cccc19961464>
36. Sessler J. L., Wang R.: J. Org. Chem. 1998, 63, 4079. <https://doi.org/10.1021/jo980194p>
37. Schalley C. A.: Int. J. Mass Spectrom. 2000, 194, 11. <https://doi.org/10.1016/S1387-3806(99)00243-2>
38. Timmerman P., Jolliffe K. A., Crego Calama M., Weidmann J.-L., Prins L. J., Cardulo F., Snellink-Ruel B. H. M., Fokens R., Nibbering N. M. M., Shinkai S., Reinhoudt D. N.: Chem. Eur. J. 2000, 6, 4104. <https://doi.org/10.1002/1521-3765(20001117)6:22<4104::AID-CHEM4104>3.0.CO;2-Q>
39. Sharma B. D., McConnell J. F.: Acta Crystallogr. 1965, 19, 797. <https://doi.org/10.1107/S0365110X65004371>
40. Bühlmann P., Simon W.: Tetrahedron 1993, 49, 7627. <https://doi.org/10.1016/S0040-4020(01)87238-0>
41. Bacaloglu R., Neamtiu F., Bacaloglu I., Ostrogovich G.: Rev. Roum. Chim. 1972, 17, 747.
42. Archer E. A., Gong H., Krische M. J.: Tetrahedron 2001, 57, 1139. <https://doi.org/10.1016/S0040-4020(00)00986-8>
43. Prins L. J., Reinhoudt D. N., Timmerman P.: Angew. Chem. 2001, 40, 2382. <https://doi.org/10.1002/1521-3773(20010702)40:13<2382::AID-ANIE2382>3.0.CO;2-G>
44. Dingley A. J., Masse J. E., Peterson R. D., Barfield M., Feigon J., Grzsiek S.: J. Am. Chem. Soc. 1999, 121, 6019. <https://doi.org/10.1021/ja9908321>
45. Limmer S.: Prog. Nucleic Acid Res. Mol. Biol. 1997, 57, 1. <https://doi.org/10.1016/S0079-6603(08)60276-7>
46. Beijer F. H., Sijbesma R. P., Kooijmam H., Spek A. L., Meijer E. W.: J. Am. Chem. Soc. 1998, 120, 6761. <https://doi.org/10.1021/ja974112a>
47. Pitha J., Norman Jones R., Pithová P.: Can. J. Chem. 1966, 44, 1045. <https://doi.org/10.1139/v66-155>
48. Sobel H. M., Tomita K., Rich A.: Proc. Natl. Acad. Sci. U.S.A. 1963, 49, 885. <https://doi.org/10.1073/pnas.49.6.885>
49. Čihák A., Šorm F.: Collect. Czech. Chem. Commun. 1965, 30, 2091. <https://doi.org/10.1135/cccc19652091>
50. Novotný L., Vachálková A., Pískala A.: Collect. Czech. Chem. Commun. 1994, 59, 1691. <https://doi.org/10.1135/cccc19941691>
51. Vachálková A., Novotný L., Pískala A.: Neoplasma 1993, 40, 289.
52. Novotný L., Vachálková A., Pískala A.: Collect. Czech. Chem. Commun. 1995, 60, 1469. <https://doi.org/10.1135/cccc19951469>
53. Novotný L., Vachálková A.: Neoplasma 1990, 37, 377.
54. Novotný L., Vachálková A.: Neoplasma 1991, 38, 223.
55. Novotný L., Vachálková A., Pískala A.: Bioelectrochem. Bioenerg. 1999, 48, 129. <https://doi.org/10.1016/S0302-4598(99)00005-7>
56. Piťhová P., Piťha J., Pískala A., Šorm F.: Collect. Czech. Chem. Commun. 1965, 30, 1626. <https://doi.org/10.1135/cccc19651626>
57. Jackson-Grusby L., Laird P. W., Magge S. N., Moeller B. J., Jaenisch R.: Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 4681. <https://doi.org/10.1073/pnas.94.9.4681>
58. DeBoer C., Bannister B.: U.S. 3 907 779; Chem. Abstr. 1976, 84, 15682.
59. Skulnick H. I.: J. Org. Chem. 1978, 43, 3188. <https://doi.org/10.1021/jo00410a020>
60. Gabbara S., Bhagwat A. S.: Biochem. J. 1995, 307.
61. Friedman S.: Mol. Pharmacol. 1981, 19, 314.
62. Benjamin E. J.: Ph.D. Thesis. University of Kansas, 1979; Diss. Abstr. 1980, 41, 208-B.
63. Pískala A., Masojídková M., Šaman D.: Collect. Czech. Chem. Commun. 1996, 61(Special Issue), 23. <https://doi.org/10.1135/cccc1996s023>
64. Perrin D. D.: Aust. J. Chem. 1963, 16, 572. <https://doi.org/10.1071/CH9630572>
65. Pískala A., Gut J.: Collect. Czech. Chem. Commun. 1963, 28, 1681. <https://doi.org/10.1135/cccc19631681>