Diastereofacial Selective Addition of Ethynylcerium Reagent and Barton-McCombie Reaction as the Key Steps for the Synthesis of C-3′-Ethynylribonucleosides and of C-3′-Ethynyl-2′-deoxyribonucleosides

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8309-8314

  Jung, Pierre M J ^a   Burger, Alain ^a   Biellmann, Jean François ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001064263     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9704568     Document Type: Article

References (52)

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2. For reviews, see for instance: (a) Périgaud C.; Gosselin G.; Imbach J.-L. Nucleosides Nudeotides 1992, 11, 903-945. (b) Herdewijn P.; Balzarini J.; De Clercq E. In Advances in Antiviral Drug Design; De Clercq E., Ed. JAI Press, Inc.: Greenwich, 1993; Vol. 1, pp 233-309.
3. See, for example: (a) Walton, E.; Jenkins, S. R.; Nutt, R. F.; Zimmerman, M.; Holly, F. W. J. Am. Chem. Soc. 1966, 88, 4524-4525. (b) Walton, E.; Jenkins, S. R.; Nutt, R. F.; Holly, F. W. J. Med. Chem. 1969, 12, 306-309. (c) Mikhailov, S., N. Nucleosides Nudeotides 1988, 7, 679-682. (d) Mikhailov, S. N.; Padyukova, N. S.; Lysov, Y. P.; Savochkina, L. P. Nucleosides Nudeotides 1991, 10, 339-343. (e) Fedorov, I. I.; Kazmina, E. M.; Novicov, N. A.; Gurskaya, G. V.; Bochkarev, A. V.; Jasko, M. V.; Victorova, L. S.; Kukhanova, M. K.; Balzarini, J.; De Clercq, E.; Krayevsky, A. A. J. Med. Chem. 1992, 35, 4567-4575.
4. See, for example: (a) Walton, E.; Jenkins, S. R.; Nutt, R. F.; Zimmerman, M.; Holly, F. W. J. Am. Chem. Soc. 1966, 88, 4524-4525. (b) Walton, E.; Jenkins, S. R.; Nutt, R. F.; Holly, F. W. J. Med. Chem. 1969, 12, 306-309. (c) Mikhailov, S., N. Nucleosides Nudeotides 1988, 7, 679-682. (d) Mikhailov, S. N.; Padyukova, N. S.; Lysov, Y. P.; Savochkina, L. P. Nucleosides Nudeotides 1991, 10, 339-343. (e) Fedorov, I. I.; Kazmina, E. M.; Novicov, N. A.; Gurskaya, G. V.; Bochkarev, A. V.; Jasko, M. V.; Victorova, L. S.; Kukhanova, M. K.; Balzarini, J.; De Clercq, E.; Krayevsky, A. A. J. Med. Chem. 1992, 35, 4567-4575.
5. See, for example: (a) Walton, E.; Jenkins, S. R.; Nutt, R. F.; Zimmerman, M.; Holly, F. W. J. Am. Chem. Soc. 1966, 88, 4524-4525. (b) Walton, E.; Jenkins, S. R.; Nutt, R. F.; Holly, F. W. J. Med. Chem. 1969, 12, 306-309. (c) Mikhailov, S., N. Nucleosides Nudeotides 1988, 7, 679-682. (d) Mikhailov, S. N.; Padyukova, N. S.; Lysov, Y. P.; Savochkina, L. P. Nucleosides Nudeotides 1991, 10, 339-343. (e) Fedorov, I. I.; Kazmina, E. M.; Novicov, N. A.; Gurskaya, G. V.; Bochkarev, A. V.; Jasko, M. V.; Victorova, L. S.; Kukhanova, M. K.; Balzarini, J.; De Clercq, E.; Krayevsky, A. A. J. Med. Chem. 1992, 35, 4567-4575.
6. See, for example: (a) Walton, E.; Jenkins, S. R.; Nutt, R. F.; Zimmerman, M.; Holly, F. W. J. Am. Chem. Soc. 1966, 88, 4524-4525. (b) Walton, E.; Jenkins, S. R.; Nutt, R. F.; Holly, F. W. J. Med. Chem. 1969, 12, 306-309. (c) Mikhailov, S., N. Nucleosides Nudeotides 1988, 7, 679-682. (d) Mikhailov, S. N.; Padyukova, N. S.; Lysov, Y. P.; Savochkina, L. P. Nucleosides Nudeotides 1991, 10, 339-343. (e) Fedorov, I. I.; Kazmina, E. M.; Novicov, N. A.; Gurskaya, G. V.; Bochkarev, A. V.; Jasko, M. V.; Victorova, L. S.; Kukhanova, M. K.; Balzarini, J.; De Clercq, E.; Krayevsky, A. A. J. Med. Chem. 1992, 35, 4567-4575.
7. See, for example: (a) Walton, E.; Jenkins, S. R.; Nutt, R. F.; Zimmerman, M.; Holly, F. W. J. Am. Chem. Soc. 1966, 88, 4524-4525. (b) Walton, E.; Jenkins, S. R.; Nutt, R. F.; Holly, F. W. J. Med. Chem. 1969, 12, 306-309. (c) Mikhailov, S., N. Nucleosides Nudeotides 1988, 7, 679-682. (d) Mikhailov, S. N.; Padyukova, N. S.; Lysov, Y. P.; Savochkina, L. P. Nucleosides Nudeotides 1991, 10, 339-343. (e) Fedorov, I. I.; Kazmina, E. M.; Novicov, N. A.; Gurskaya, G. V.; Bochkarev, A. V.; Jasko, M. V.; Victorova, L. S.; Kukhanova, M. K.; Balzarini, J.; De Clercq, E.; Krayevsky, A. A. J. Med. Chem. 1992, 35, 4567-4575.
8. The deletion of the 3′-hydroxyl group is not a sine qua non condition for anti-HIV activity. Nucleoside triphosphates with a remaining 3′-hydroxyl group but where the hydrogen at C-4′ has been replaced by an azido or an acylated group have been prepared and their action on HIV-1 RT has been studied; see: (a) Maag, H.; Kydzewski, R. M.; McRoberts, M. J.; Crawford-Ruth, D.; Verheyden, J. P. H.; Prisbe, E. J. J. Med. Chem. 1992, 35, 1440-1451. (b) Chen, M. S.; Suttmann, R. T.; Papp, E.; Cannon, P. D.; McRoberts, M. J.; Bach, C.; Copeland, W. C.; Wang, T. S.-F. Biochemistry, 1993, 32, 6002-6010. (c) Marx, A.; MacWilliams, M. P.; Bickle, T. A.; Schwitter, U.; Giese, B. J. Am. Chem. Soc. 1997, 119, 1131-1132.
9. The deletion of the 3′-hydroxyl group is not a sine qua non condition for anti-HIV activity. Nucleoside triphosphates with a remaining 3′-hydroxyl group but where the hydrogen at C-4′ has been replaced by an azido or an acylated group have been prepared and their action on HIV-1 RT has been studied; see: (a) Maag, H.; Kydzewski, R. M.; McRoberts, M. J.; Crawford-Ruth, D.; Verheyden, J. P. H.; Prisbe, E. J. J. Med. Chem. 1992, 35, 1440-1451. (b) Chen, M. S.; Suttmann, R. T.; Papp, E.; Cannon, P. D.; McRoberts, M. J.; Bach, C.; Copeland, W. C.; Wang, T. S.-F. Biochemistry, 1993, 32, 6002-6010. (c) Marx, A.; MacWilliams, M. P.; Bickle, T. A.; Schwitter, U.; Giese, B. J. Am. Chem. Soc. 1997, 119, 1131-1132.
10. The deletion of the 3′-hydroxyl group is not a sine qua non condition for anti-HIV activity. Nucleoside triphosphates with a remaining 3′-hydroxyl group but where the hydrogen at C-4′ has been replaced by an azido or an acylated group have been prepared and their action on HIV-1 RT has been studied; see: (a) Maag, H.; Kydzewski, R. M.; McRoberts, M. J.; Crawford-Ruth, D.; Verheyden, J. P. H.; Prisbe, E. J. J. Med. Chem. 1992, 35, 1440-1451. (b) Chen, M. S.; Suttmann, R. T.; Papp, E.; Cannon, P. D.; McRoberts, M. J.; Bach, C.; Copeland, W. C.; Wang, T. S.-F. Biochemistry, 1993, 32, 6002-6010. (c) Marx, A.; MacWilliams, M. P.; Bickle, T. A.; Schwitter, U.; Giese, B. J. Am. Chem. Soc. 1997, 119, 1131-1132.
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51. One of the reasons we have been interested by the ethynyl group, relative to alkyl and alkenyl groups, is its high electronegativity, which is larger than a chloride atom and comparable to a cyano group. By electron withdrawing, the ethynyl group might lower the nucleophilicity of the 3′ tertiary alcohol; see: Wells, P. R. Prog. Phys. Org. Chem. 1966, 6, 111-145.
52. Because of its important cytoxicity, compound 4a was retained for subsequent investigations upon a panel of cultured malignant cells. Matsuda and his collaborators have described the high potent anti-tumor activity of compound 4a against human tumor cells in vitro and in vivo; see ref 11 and: Weltin, D.; Jung, P. M. J.; Holl, V.; Dauvergne, J.; Burger, A.; Dufour, P.; Aubertin, A. M.; Bischoff, P.; Biellmann J. F. Submitted for publication.