Cocyclotrimerization of 6-alkynylpurines with α,ω-diynes as a novel approach to biologically active 6-arylpurines

Journal of Organic Chemistry

Volumn 69, Issue 26, 2004, Pages 9224-9233

  Turek, Pavel ^a,b   Kotora, Martin ^a,b   Tišlerová, Iva ^a   Hocek, Michal ^b   Votruba, Ivan ^b   Císařová, Ivana ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; ETHERS; STOICHIOMETRY; TRANSITION METAL COMPOUNDS;

CYCLOTRIMERIZATION; CYTOSTATIC ACTIVITIES;

ORGANOMETALLICS;

6 (1,3 DIHYDROISOBENZOFURAN 5 YL) 9 (TETRAHYDROPYRAN 2 YL) 9H PURINE; 6 [6 BUTYL 2,2 BIS(CARBOXYETHYL)INDAN 5 YL] 9 (TETRAHYDROPYRAN 2 YL) 9H PURINE; 6 [6 PHENYL 2 CYANO 2 (CARBOXYETHYL)INDAN 5 YL] 9 (TETRAHYDROPYRAN 2 YL) 9H PURINE; 6 [6 PHENYL 2,2 BIS(CARBOXYETHYL)INDAN 5 YL] 9H PURINE; ALKYNE; ALKYNYL GROUP; ETHER DERIVATIVE; METAL COMPLEX; NICKEL; NICKEL COMPLEX; PHOSPHINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PURINE DERIVATIVE; REDUCING AGENT; TRANSITION ELEMENT; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; COMPARATIVE STUDY; CYCLIZATION; CYCLOTRIMERIZATION; CYTOSTASIS; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; ISOMERIZATION; QUANTUM YIELD; REACTION ANALYSIS; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION;

MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; POLYMERS; PURINES; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 10844272377     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0486342     Document Type: Article

References (81)

1. Cocuzza, A. J.; Chidester, D. R.; Culp, S.; Fitzgerald, L.; Gilligan, P. Bioorg. Med. Chem. Lett. 1999, 9, 1063-1066.
2. (a) Bakkestuen, A. K.; Gundersen, L.-L.; Langli, G.; Liu, F.; Nolsøe, J. M. J. Bioorg. Med. Chem. Lett. 2000, 10, 1207-1210.
3. (b) Andresen, G.; Gundersen, L.-L.; Nissen-Meyer, J.; Rise, F.; Spilsberg, B. Bioorg. Med. Chem. Lett. 2002, 12, 567-569.
4. (c) Gundersen, L.-L.; Nissen-Meyer, J.; Spilsberg, D. J. Med. Chem. 2002, 45, 1383-1386.
5. (a) Hocek, M.; Holý, A.; Votruba, I.; Dvořá ková, H. J. Med. Chem. 2000, 43, 1817-1825.
6. (b) Hocek, M.; Holý, A.; Votruba, I.; Dvořá ková, H. Collect. Czech. Chem. Commun. 2000, 65, 1683-1697.
7. (c) Hocek, M.; Holý, A.; Votruba, L; Dvořá ková, H. Collect. Czech. Chem. Commun. 2001, 66, 483-499.
8. (d) Hocek, M.; Holý, A.; Dvořáková, H. Collect. Czech. Chem. Commun. 2002, 67, 325-335.
9. (f) Hocek, M.; Hocková, D.; Štambaský, J. Collect. Czech. Chem. Commun. 2003, 68, 837-848.
10. (a) Fujiwara, T.; Kimoto, M.; Sugiyama, H.; Hirao, I.; Yokoyama, S. Bioorg. Med. Chem. Lett. 2001, 11, 2221-2223.
11. (b) Hirao, I.; Ohtsuki, T.; Fujiwara, T.; Mitsui, T.; Yokogawa, T.; Okuni, T.; Nakayama, H.; Takio, K.; Yabuki, T.; Kigawa, T.; Kodama, K.; Yokogawa, T.; Nishikawa, K.; Yokoyama, S. Nat. Biotechnol. 2002, 20, 177-182.
12. Havelková, M.; Dvořák, D.; Hocek, M. Tetrahedron 2002, 58, 7431-7435.
13. (a) Kool, E. T. Acc. Chem. Res. 2002, 35, 936-943.
14. (b) Kool, E. T.; Morales, J. C.; Guckian, K. M. Angew. Chem., Int. Ed. 2000, 39, 990-1009.
15. (c) Ogawa, A. K.; Abou-Zied, O. K.; Tsui, V.; Jimenez, R.; Case, D. A.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 9917-9920.
16. (d) Wu, Y. Q.; Ogawa, A. K.; Berger, M.; McMinn, D. L.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 7621-7632.
17. (e) Guckian, K. M.; Krugh, T. R.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 6841-6847.
18. (f) Parsch, J.; Engels, J. W. J. Am. Chem. Soc. 2002, 124, 5664-5672.
19. (g) McMinn, D. L.; Ogawa, A. K.; Wu, Y. Q.; Liu, J. Q.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586.
20. (h) Tae, E. L.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2001, 123, 7439-7440.
21. Review: Hocek, M. Eur. J. Org. Chem. 2003, 245-254.
22. Examples: Arylmagnesium halides: (a) Estep, K. G.; Josef, K. A.; Bacon, E. R.; Carabates, P. M.; Rumney, S., IV; Pilling, G. M.; Krafte, D. S.; Volberg, W. A.; Dillon, K.; Dugrenier, N.; Briggs, G. M.; Canniff, P. C.; Gorczyca, W. P.; Stankus, G. P.; Ezrin, A. M. J. Med. Chem. 1995, 38, 2582-2595.
23. Arylzinc halides: (b) Česnek, M.; Hocek, M.; Holý, A. Collect. Czech. Chem. Commun. 2000, 65, 1357-1373.
24. Arylstannanes: (c) Langli, G.; Gundersen L.-L.; Rise. F. Tetrahedron 1996, 52, 5625-5638.
25. Arylboronic acids: (d) Havelková, M.; Dvořák, D.; Hocek, M. Synthesis 2001, 1704-1710.
26. (a) Frühauf, H.-H. Chem. Rev. 1997, 97, 523-596.
27. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
28. (c) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier Science, Ltd.: Oxford, 1995; Vol. 12; pp 741-770.
29. (d) Schore, N. E. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press, Ltd.: Oxford, 1991; Vol. 5; pp 1129-1162.
30. (e) Harrington, P. J. Transition Metals in Total Synthesis; John Wiley & Sons: New York, 1990; pp 200-240.
31. (f) Schore, N. E. Chem. Rev. 1988, 88, 8; 1081-1119.
32. (g) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539-556.
33. (h) Nicolaou, K. C.; Sorensen, E. J. Classics in Organic Synthesis (Targets, Strategies, Methods); VCH: Weinheim, 1996.
34. (i) Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905.
35. (j) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2916.
36. Preliminary communication: Turek, P.; Kotora, M.; Hocek, M.; Císařová, I. Tetrahedron Lett. 2003, 44, 785-788.
37. (a) Müller, E. Synthesis 1974, 761-774.
38. (b) Grigg, R.; Scott, R.; Stevenson, P. Tetrahedron Lett. 1982, 23, 2691-2692.
39. (c) Grigg, R.; Scott, R.; Stevenson, P. J. Chem. Soc., Perkin Trans. 1 1988, 1357-1364.
40. (d) Magnus, P.; Witty, D.; Stamford, A. Tetrahedron Lett. 1993, 34, 23-26.
41. (e) McDonald, F. E.; Zhu, H. Y.; Holmquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605-6606.
42. (f) Grigg, R.; Sridharan, V.; Wang, J.; Xu, J. P. Tetrahedron 2000, 56, 8967-8976.
43. (g) McDonald, F. E.; Smolentsev, V. Org. Lett. 2002, 4, 745-748.
44. (a) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430.
45. (b) Witulski, B.; Stengel, T.; Fernandez-Hernandez, J. M. Chem. Commun. 2000, 1965-1966.
46. (c) Witulski, B.; Zimmermann, A Synlett 2002, 1855-1859.
47. (d) Witulski, B.; Zimmermann, A.; Gowans, N. D. Chem. Commun. 2002, 2984-2985.
48. (e) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281-3284.
49. (a) Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561-3564.
50. (b) Kotha, S.; Mohanraja, K.; Durani, S. Chem. Commun. 2000, 1909-1910.
51. (c) Kotha, S.; Sreenivasachary, N. Eur. J. Org. Chem. 2001, 3375-3383.
52. (d) Kotha, S, Brahmachary, E. Bioorg. Med. Chem. 2002, 10, 2291-2295.
53. (e) Kotha, S.; Brahmachary, E. J. Organomet. Chem. 2004, 689, 158-163.
54. Dufková, L.; Císařová, I., Štepnička, P.; Kotora, M. Eur. J. Org. Chem. 2003, 2882-2887.
55. Field, L. D.; Ward, A. J.; Turner, P. Aust. J. Chem. 1999, 52, 1085-1092.
56. 3/Mn was recently shown to effect cyclotrimerization of alkynes, see: Slowinski, F.; Aubert, C.; Malacria, M. Adv. Synth. Catal. 2001, 343, 64-67.
57. 2(dppe)/Zn system is good for cyclotrimerization of alkynes and cocyclotrimerization of alkynes with allenes: (a) Jeevanandam, A.; Korivi, R. J.; Huang, I.; Cheng, C.-H. Org. Lett. 2002, 4, 807-810.
58. (b) Shunmugasundaram, M.; Wu, M. S.; Cheng, C.-H. Org. Lett. 2001, 3, 4233-4236.
59. (a) Sato, Y.; Nishimata, T.; Mori, M. J. Org. Chem. 1994, 59, 6133-6135.
60. (b) Sato, Y.; Nishimata, T.; Mori, M. Heterocycles 1997, 44, 443-457
61. (c) Sato, Y.; Ohashi, K.; Mori, M. Tetrahedron Lett. 1999, 40, 5231-5234.
62. (a) Stará, I. G.; Starý, I.; Kollárovič, A.; Teplý, F.; Vyskočil, Š.; Šaman, D. Tetrahedron Lett. 1999, 40, 1993-1996.
63. (b) Hocek, M.; Stará, I. G.; Starý, I.; Dvořáková, H. Tetrahedron Lett. 2001, 42, 519-522.
64. (c) Teplý, F.; Stará, I. G.; Starý, I.; Kollárovič, A.; Šaman, D.; Rulíšek, L.; Fiedler, P. J. Am. Chem. Soc. 2002, 124, 9175-9180.
65. (d) Hocek, M.; Stará, I. G.; Starý, I.; Dvořáková, H. Collect. Czech. Chem. Commun. 2002, 67, 1223-1235.
66. (e) Stará, I. G.; Starý, I.; Kollárovič A.; Teplý, F.; Šaman, D.; Fiedler, P. Collect. Czech. Chem. Commun. 2003, 68, 917-930.
67. (f) Teplý, F.; Stará, I. G.; Starý, I.; Kollárovič, A.; Šaman, D.; Fiedler, P.; Vyskočil, Š. J. Am. Chem. Soc. 2003, 68, 5193-5197.
68. For nickel-mediated cyclotrimerizations, see: (a) Bhatarah, P.; Smith, E. H. J. Chem. Soc., Perkin Trans 1 1990, 2603-2606.
69. (b) Bhatarah, P.; Smith, E. H. J. Chem. Soc., Chem. Commun. 1991, 277-278.
70. (c) Bhatarah, P.; Smith, E. H. J. Chem. Soc., Perkin Trans 1 1992, 2163-2168.
71. Coordination of nitriles to Ni, see: Eisch, J. J.; Ma, X.; Han, K. I.; Gitau, J. A.; Krüger, C. Eur. J. Inorg. Chem. 2001, 77-88.
72. Takeuchi, R.; Tanaka, S.; Nakaya, Y. Tetrahedron Lett. 2001, 42, 2991-2994.
73. Some typical examples of group VIII complexes with nucleobases: For Co, see: (a) Yamanari, K.; Kida, K.; Yamamoto, M.; Fujihara, T.; Fuyuhiro, A.; Kaizaki, S. J. Chem. Soc., Dalton Trans. 1998, 305-309.
74. (b) Yamanari, K.; Fukuda, I.; Kawamoto, T.; Kushi, Y.; Fuyuhiro, A.; Kubota, N.; Fukuo, T.; Arakawa, R. Inorg. Chem. 1998, 37, 5611-5618.
75. For Rh and Ir, see: (c) Abbott, D. W.; Woods, C. Inorg. Chem. 1983, 22, 597-602.
76. (d) Abbott, D. W.; Woods, C. Inorg. Chem. 1983, 22, 2918-2923.
77. (e) Annen, P.; Schildberg, S.; Sheldrick, W. S. Inorg. Chim. Acta 2000, 307, 115-124.
78. (f) Yamanari, K.; Ito, R.; Yamamoto, S.; Konno, T.; Fuyuhiro, A.; Fujioka, K.; Arakawa, R. Inorg. Chem. 2002, 41, 6824-6830.
79. (g) Yamanari, K.; Ito, R., Yamamoto, S.; Konno, T.; Fuyuhiro, A.; Kobayashi, M.; Arakawa, R. J. Chem. Soc. Dalton Trans. 2003, 380-386.
80. Hocek, M.; Holý, A. Collect. Czech. Chem. Commun. 1995, 60, 1386-1389.
81. For experimental details of the assays, see ref 3a.