Hydrogermylation of 5-ethynyluracil nucleosides: Formation of 5-(2-germylvinyl)uracil and 5-(2-germylacetyl)uracil nucleosides

Journal of Organic Chemistry

Volumn 78, Issue 11, 2013, Pages 5761-5767

  Liang, Yong ^a   Pitteloud, Jean Philippe ^a   Wnuk, Stanislaw F ^a  

^a FLORIDA INTERNATIONAL UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; REACTION INTERMEDIATES;

ACTIVATED COMPLEX; HYDROGERMYLATION; PYRIMIDINE NUCLEOSIDES; QUANTITATIVE YIELDS; STEREO-SELECTIVE; SUBSEQUENT HYDROLYSIS; THERMAL ISOMERIZATIONS; TRIMETHYLSILYL;

BIOMOLECULES;

1 (2 DEOXY 3,5, DI O 4 TOLUOYL BETA DEXTRO ERYTHRO PENTOFURANOSYL) 5 [2 (TRIPHENYLGERMYL)ACETYL]URACIL; 1 (2,3,5 TRI O ACETYL BETA DEXTRO ARABINOFURANOSYL) 5 [2 (TRIMETHYLGERMYL)ETHENYL)URACIL; 1 (2,3,5 TRI O ACETYL BETA DEXTRO ARABINOFURANOSYL) 5 [2 (TRIPHENYLGERMYL)ACETYL]URACIL; 1 (2,3,5 TRI O ACETYL BETA DEXTRO ARABINOFURANOSYL) 5 [2 (TRIPHENYLGERMYL)ETHENYL]URACIL; 1 (2,3,5 TRI O ACETYL BETA DEXTRO ARABINOFURANOSYL) 5 [2 [TRIS (TRIMETHYLSILYL)GERMYL)ETHENYL)URACIL; 1 N BENZYL 5 [2 (TRIPHENYLGERMNYL)ACETYL]URACIL; 5 (2 GERMYLACETYL) URACIL NUCLEOSIDE DERIVATIVE; 5 (2 GERMYLVINYL)URACIL NUCLEOSIDE DERIVATIVE; 5 [2 TRIPHENYLGERMYL)ACETYL] 2',3',5' TRI O 4 TOLUOYLURIDINE; NUCLEOSIDE DERIVATIVE; OXYGEN; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DEPROTECTION REACTION; DRUG SYNTHESIS; FRAGMENTATION REACTION; HYDROGERMYLATION; HYDROLYSIS; ISOMERIZATION; STEREOCHEMISTRY;

EID: 84879290481     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400590z     Document Type: Article

References (46)

1. Machida, H. and Sakata, S. In Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C. K. and Baker, D. C., Eds.; Plenum Press: New York, 1993; pp 245-264.
2. De Clercq, E.; Descamps, J.; De Somer, P.; Barr, P. J.; Jones, A. S.; Walker, R. T. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 2947-2951
3. Machida, H.; Kuninaka, A.; Yoshino, H.; Ikeda, K.; Mizuno, Y. Antimicrob. Agents Chemother. 1980, 17, 1030-1031
4. Robins, M. J.; Barr, P. J. J. Org. Chem. 1983, 48, 1854-1862
5. Agrofoglio, L. A.; Gillaizeau, I.; Saito, Y. Chem. Rev. 2003, 103, 1875-1916
6. Dougan, H.; Rennie, B. A.; Lyster, D. M.; Sacks, S. L. Appl. Radiat. Isot. 1994, 45, 795-801
7. Yu, C.-S.; Oberdorfer, F. Synlett 2000, 86-88
8. Yu, C.-S.; Wu, C.-H.; Chiang, L.-W.; Wang, R.-T.; Wang, H.-Y.; Yeh, C.-H.; Lin, K.-I. Chem. Lett. 2005, 34, 1390-1391
9. Yu, C.-S.; Chiang, L.-W.; Wu, C.-H.; Wang, R.-T.; Chen, S.-W.; Wang, H.-Y.; Yeh, C.-H. Nucl. Med. Biol. 2006, 33, 367-370
10. Robins, M. J.; Manfredini, S.; Wood, S. G.; Wanklin, R. J.; Rennie, B. A.; Sacks, S. L. J. Med. Chem. 1991, 34, 2275-2280
11. Robins, M. J.; Manfredini, S. Tetrahedron Lett. 1990, 31, 5633-5636
12. Morin, K. W.; Atrazheva, E. D.; Knaus, E. E.; Wiebe, L. I. J. Med. Chem. 1997, 40, 2184-2190
13. The Chemistry of Organic Germanium, Tin and Lead Compounds; Patai, S.; Rappoport, Z., Eds.; John Wiley & Sons: Chichester, UK, 1995; Vol. 1; 2002; Vol. 2.
14. Lukevics, E.; Ignatovich, L. In Metallotherapeutic Drugs and Metal-Based Diagnostic Agents; Gielen, M.; Tiekink, E. R. T., Eds.; Wiley: New York, 2005; pp 279-295.
15. Lukevics, E.; Ignatovich, L. In The Chemistry of Organic Germanium, Tin and Lead Compounds; Rappoport, Z., Ed.; Wiley: New York, 2002; pp 1653-1683.
16. Trushule, M.; Kupche, é.; Augustane, I.; Verovskii, N.; Lukevits, é.; Baumane, L.; Gavar, R.; Stradyn, Y. Chem. Heterocycl. Compd. 1991, 27, 1358-1364
17. Lukevics, E.; Ignatovich, L.; Shilina, N.; Kemme, A.; Sjakste, N. Metal-Based Drugs 1994, 1, 65-72
18. Chem. Abstr. 1992, 121, 134303.
19. Mel'nik, S. l.; Bakhmedova, A. A.; Nedorezova, T. P.; Iartseva, I. V.; Zhukova, O. S.; Dobrynin, Y. V.; Preobrazhenskaya, M. N.; Kolesnikov, S. P.; Li, V. Y. Bioorg. Khim. 1985, 11, 1248-1252
20. Chem. Abstr. 1985, 105, 79283.
21. Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468-3470
22. Kinoshita, H.; Nakamura, T.; Kakiya, H.; Shinokubo, H.; Matsubara, S.; Oshima, K. Org. Lett. 2001, 3, 2521-2524
23. Nozaki, K.; Ichinose, Y.; Wakamatsu, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1990, 63, 2268-2272
24. Schwier, T.; Gevorgyan, V. Org. Lett. 2005, 7, 5191-5194
25. Bernardoni, S.; Lucarini, M.; Pedulli, G. F.; Valgimigli, L.; Gevorgyan, V.; Chatgilialoglu, C. J. Org. Chem. 1997, 62, 8009-8014
26. David-Quillot, F.; Thiery, V.; Abarbri, M.; Thibonnet, J.; Besson, T.; Duchene, A. Main Group Met. Chem. 2007, 30, 235-244
27. Wnuk, S. F.; Garcia, P. I., Jr.; Wang, Z. Org. Lett. 2004, 6, 2047-2049
28. Sharma, R. A.; Kavai, I.; Hughes, R. G.; Bobek, M. J. Med. Chem. 1984, 27, 410-412
29. Ichinose, Y.; Nozaki, K.; Wakamatsu, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1987, 28, 3709-3712
30. Wnuk, S. F.; Sacasa, P. R.; Restrepo, J. Nucleosides, Nucleotides Nucleic Acids 2009, 28, 537-549
31. Oda, H.; Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 3221-3224
32. Oda, H.; Oshima, K.; Nozaki, H. Chem. Lett. 1985, 53-56
33. Cai, C.; Vasella, A. Helv. Chim. Acta 1996, 79, 255-268
34. Wang, Z.; Wnuk, S. F. J. Org. Chem. 2005, 70, 3281-3284
35. Prachayasittikul, S.; Sornsongkhram, N.; Pingaew, R.; Worachartcheewan, A.; Ruchirawat, S.; Prachayasittikul, V. Molecules 2009, 14, 2768-2779
36. Fahrig, R.; Eger, K.; Fuehrer, M.; Heinze, N.; Klemm, M.; Heinrich, J.-C., 2009, WO 2009156182
37. Chem. Abstr. 2009, 152, 119663.
38. Chatgilialoglu, C.; Newcomb, M. Adv. Organomet. Chem. 1999, 44, 67-112
39. Chatgilialoglu, C.; Timokhin, V. I.; Zaborovskiy, A. B.; Lutsyk, D. S.; Prystansky, R. E. J. Chem. Soc., Perkin Trans. 2 2000, 577-582
40. Barr, P. J.; Chananont, P.; Hamor, T. A.; Jones, A. S.; O'Leary, M. K.; Walker, R. T. Tetrahedron 1980, 36, 1269-1273
41. Lutsenko, I. F.; I. Baukov, Y.; Dudukina, O. V.; Kramarova, E. N. J. Organomet. Chem. 1968, 11, 35-48
42. Barr, P. J.; Jones, A. S.; Serafinowski, P.; Walker, R. T. J. Chem. Soc., Perkin Trans. 2 1978, 1, 1263-1267
43. Jones, A. S.; Verhelst, G.; Walker, R. T. Tetrahedron Lett. 1979, 20, 4415-4418
44. Jones, A. S.; Rahim, S. G.; Walker, R. T.; De Clercq, E. J. Med. Chem. 1981, 24, 759-760
45. Nair, V.; Chi, G.; Uchil, V. R., 2007, WO 2007106450
46. Chem. Abstr. 2007, 147, 385768. Sciences/National Cancer Institute