Collect. Czech. Chem. Commun. 2011, 76, 1361-1378
https://doi.org/10.1135/cccc2011114
Published online 2011-11-20 19:55:52

N6-substituted adenosines. Cytokinin and antitumor activities

Svetlana V. Kolyachkinaa, Vitali I. Tararova, Cyril S. Alexeeva, Dmitry M. Krivosheevb, Georgy A. Romanovb, Evgenia V. Stepanovac, Eliso S. Solomkoc, Andrey N. Inshakovc and Sergey N. Mikhailova,*

a Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov str. 32, 119991 Moscow, Russia
b Institute of Plant Physiology, Russian Academy of Sciences, Botanicheskaya 35, 127276 Moscow, Russia
c N.N. Blokhin Cancer Research Center, Kashirskoy shosse 24, 115478 Moscow, Russia

References

1a. Romanov G. A.: Rus. J. Plant Physiol. 2009, 56, 268. <https://doi.org/10.1134/S1021443709020174>
1b. Sakakibara H.: Annu. Rev. Plant Biol. 2006, 57, 431. <https://doi.org/10.1146/annurev.arplant.57.032905.105231>
2a. Miller C. O., Skoog F., von Saltza M. H., Strong F. M.: J. Am. Chem. Soc. 1955, 77, 1392. <https://doi.org/10.1021/ja01610a105>
2b. Miller C. O., Skoog F., Okumura F. S., von Saltza M. H., Strong F. M.: J. Am. Chem. Soc. 1956, 78, 1375. <https://doi.org/10.1021/ja01588a032>
3. Barciszewski J., Siboska G. E., Pedersen B. O., Clark B. F. C., Rattan S. I. S.: FEBS Lett. 1997, 414, 457. <https://doi.org/10.1016/S0014-5793(97)01037-5>
4. Rozenski J., Crain P. F., McCloskey J. A.: Nucleic Acids Res. 1999, 27, 196. <https://doi.org/10.1093/nar/27.1.196>
5a. Laezza C., Notarnicola M., Caruso M. G., Messa C., Macchia M., Bertini S., Minutolo F., Portella G., Fiorentino L., Stingo S., Bifulco M.: FASEB J. 2006, 20, 412. <https://doi.org/10.1096/fj.05-4044lsf>
5b. Voller J., Zatloukal M., Lenobel R., Doležal K., Béreš T., Kryštof V., Spíchal L., Niemann P., Dzubák P., Hajdúch M., Strnad M.: Phytochemistry 2010, 71, 1350. <https://doi.org/10.1016/j.phytochem.2010.04.018>
6a. Jones J. W., Robins R. K.: J. Am. Chem. Soc. 1963, 85, 193. <https://doi.org/10.1021/ja00885a019>
6b. Robins M. J., Trips E. M.: Biochemistry 1973, 12, 2179. <https://doi.org/10.1021/bi00736a001>
6c. Timofeev E. N., Mikhailov S. N., Zuev A. N., Efimtseva E. V., Herdewijn P., Somers R. L., Lemaitre M. M.: Helv. Chim. Acta 2007, 90, 928. <https://doi.org/10.1002/hlca.200790093>
6d. Ottria R., Casati S., Manzocchi A., Baldoli E., Mariotti M., Maier J. A. M., Ciuffreda P.: Bioorg. Med. Chem. 2010, 18, 4249. <https://doi.org/10.1016/j.bmc.2010.04.093>
7a. Vorbrüggen H., Krolikiewicz K.: Liebigs Ann. Chem. 1976, 745.
7b. Wan Z.-K., Binnun E., Wilson D. P., Lee J.: Org. Lett. 2005, 7, 5877. <https://doi.org/10.1021/ol052424+>
7c. Wan Z.-K., Wacharasindhu S., Binnun E., Mansour T.: Org. Lett. 2006, 8, 2425. <https://doi.org/10.1021/ol060815y>
8a. Fleysher M. C., Hakala M. T., Bloch A., Hall R. H.: J. Med. Chem. 1968, 11, 717. <https://doi.org/10.1021/jm00310a018>
8b. Fleysher M. C., Bloch A., Hakala M. T., Nichol C. A.: J. Med. Chem. 1969, 12, 1056. <https://doi.org/10.1021/jm00306a021>
8c. Fleysher M. C.: J. Med. Chem. 1972, 15, 187. <https://doi.org/10.1021/jm00272a015>
8d. Doležal K., Popa I., Hauserová E., Spíchal L., Chakrabarty K., Novák O., Kryštof V., Voller J., Holub J., Strnad M.: Bioorg. Med. Chem. 2007, 15, 3737. <https://doi.org/10.1016/j.bmc.2007.03.038>
8e. Ottria R., Casati S., Baldoli E., Maier J. A. M., Ciuffreda P.: Bioorg. Med. Chem. 2010, 18, 8396. <https://doi.org/10.1016/j.bmc.2010.09.030>
9. Lescrinier E., Pannecouque C., Rozenski J., van Aerschot A., Kerremans L., Herdewijn P.: Nucleosides, Nucleotides Nucleic Acids 1996, 15, 1863.
10a. Aritomo K., Wada T., Sekine M. J.: J. Chem. Soc., Perkin Trans. 1 1995, 1837. <https://doi.org/10.1039/p19950001837>
10b. Fletcher S.: Tetrahedron Lett. 2010, 51, 2948. <https://doi.org/10.1016/j.tetlet.2010.03.103>
11. A review on Mitsunobu reaction: Kumara Swamy K. C., Bhuvan Kumar N. N., Balaraman E., Pavan Kumar K. V. P.: Chem. Rev. 2009, 109, 2551. <https://doi.org/10.1021/cr800278z>
12. Tararov V. I., Kolyachkina S. V., Alexeev C. S., Mikhailov S. N.: Synthesis 2011, 2483.
13. Jones J. W., Robins R.: J. Am. Chem. Soc. 1962, 84, 1914. <https://doi.org/10.1021/ja00869a029>
14. Leonard N. J., Fujii T: J. Am. Chem. Soc. 1963, 85, 3719. <https://doi.org/10.1021/ja00905a056>
15a. Mikhailov S. N., Blaton N., Rozenski J., Balzarini J., De Clercq E., Herdewijn P.: Nucleosides Nucleotides 1996, 15, 867.
15b. Efimtseva E. V., Mikhailov S. N., Fomicheva M. V., Meshkov S. V., Rodionov M. S., Khomutov A. R., De Clercq E.: Bioorg. Khim. 1998, 24, 16.
15c. Holý A., Günter J., Dvořáková H., Masojídková M., Andrei G., Snoeck R., Balzarini J., De Clercq E.: J. Med. Chem. 1999, 42, 2064. <https://doi.org/10.1021/jm9811256>
15d. Enkvist E., Raidaru G., Uri A., Patel R., Redick C., Boyer J. L., Subbi J., Tammiste I.: Nucleosides Nucleotides 2006, 25, 141.
16. Jones J. W., Robins R. K.: J. Am. Chem. Soc. 1963, 85, 193. <https://doi.org/10.1021/ja00885a019>
17. Seebach D., Beck A. K., Studer A. in: Modern Synthetic Methods (B. Ernst and C. Leumann, Eds), p. 27. Verlag Helvetica Chimica Acta, Basel 1995.
18. Romanov G. A., Kieber J. J., Schmülling T.: FEBS Lett. 2002, 515, 39. <https://doi.org/10.1016/S0014-5793(02)02415-8>
19. Romanov G. A., Getman I. A., Schmülling T.: Plant Growth Regul. 2000, 34, 337. <https://doi.org/10.1023/A:1010731228389>
20. Spinola M., Colombo F., Falvella S., Dragani T. A.: Int. J. Cancer 2007, 120, 2744. <https://doi.org/10.1002/ijc.22601>
21. Toschi L., Finocchiaro G., Bartolini S., Gioia V., Cappuzzo F.: Future Oncol. 2005, 1, 7. <https://doi.org/10.1517/14796694.1.1.7>
22. Vartanian A. A., Burova O. S., Stepanova E. V., Baryshnikov A. Y.: Melanoma Res. 2007, 1, 1. <https://doi.org/10.1097/CMR.0b013e3280112b76>
23. O’Connell K. A., Edidin M.: J. Immunol. 1990, 2, 521.
24. Ikehara M., Uesugi S., Kaneko M. in: Nucleic Acid Chemistry (L. B. Townsend and R. S. Tipson, Eds), part 2, p. 610. Wiley, New York 1970.