An efficient synthesis of acyclic N7- and N9-adenine nucleosides via alkylation with secondary carbon electrophiles to introduce versatile functional groups at the C-1 position of acyclic moiety

Nucleosides, Nucleotides and Nucleic Acids

Volumn 25, Issue 2, 2006, Pages 121-140

  Kotian, Pravin L ^a   Kumar, V Satish ^a   Lin, Tsu Hsing ^a   El Kattan, Yahya ^a   Ghosh, Ajit ^a   Wu, Minwan ^a   Cheng, Xiaogang ^a   Bantia, Shanta ^a   Babu, Yarlagadda S ^a   Chand, Pooran ^a  

^a BIOCRYST PHARMACEUTICALS INC   (United States)

Author keywords

N alkylation of adenine; N7 and N9 Adenine nucleosides

Indexed keywords

2 [6 (DIMETHYLAMINOMETHYLENEAMINO)PURIN 7 YL]PENT 4 ENOIC ACID ETHYL ESTER; 2 BROMOPENT 4 ENOIC ACID ETHYL ESTER; 4 PENTENOIC ACID; [2 (6 AMINO PURIN 7 YL) 4 HYDROXY BUTOXYMETHYL]PHOSPHONIC ACID; [2 (6 AMINO PURIN 7 YL)PENT 4 ENYLOXYMETHYL]PHOSPHONIC ACID; [3 (6 AMINO PURIN 7 YL) 4 HYDROXY BUTOXYMETHYL]PHOSPHONIC ACID; ACYCLIC NUCLEOSIDE; ADENIN 9 YL PENT 4 ENOIC ACID ETHYL ESTER; ADENINE; ADENINE DERIVATIVE; CARBON; FORMAMIDINE; FUNCTIONAL GROUP; N,N DIMETHYL N' (9H PURIN 6 YL)FORMAMIDINE; PHOSPHONIC ACID DERIVATIVE; PYROPHOSPHORYLPHOSPHONATE; UNCLASSIFIED DRUG;

ALKYLATION; ANTIVIRAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMER; NONHUMAN; SUBSTITUTION REACTION;

ADENINE; ALKYLATION; ANTIVIRAL AGENTS; CARBON; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; NUCLEOSIDES;

EID: 31644447942     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770500446816     Document Type: Article

References (44)

1. (a) Schaeffer, H.J.; Beauchamp, L.; de Miranda, P.; Elion, G.B.; Bauer, D.J.; Collins, P. 9-(2-Hydroxyethoxymethyl)guanine activity against viruses of the herpes group. Nature (London) 1978, 272(5654), 583-585;
2. (b) Elion, G.B.; Furman, P.A.; Fyfe, J.A.; de Miranda, P.; Beauchamp, L.; Schaeffer, H.J. Selectivity of action of an antiherpetic agent, 9-(2-hydroxyethoxymethyl)guanine. Proc. Natl. Acad. Sci. U.S.A. 1977, 74(12), 5716-5720;
3. (c) Collins, P.; Bauer, D.J. The activity in vitro against herpes virus of 9-(2-hydroxyethoxymethyl)guanine (acycloguanosine), a new antiviral agent. J. Antimicrob. Chemother. 1979, 5(4), 431-436.
4. (a) Smith, K.O.; Galloway, K.S.; Kennell, W.L.; Ogilvie, K.K.; Radatus, B.K. A new nucleoside analog, 9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl] guanine, highly active in vitro against herpes simplex virus types 1 and 2. Antimicrob. Agents Chemother. 1982, 22(1), 55-61;
5. (b) Ashton, W.T.; Karkas, J.D.; Field, A.K.; Tolman, R.L. Activation by thymidine kinase and potent antiherpetic activity of 2′-nor-2′- deoxyguanosine (2′NDG). Biochem. Biophys. Res. Commun. 1982, 108(4), 1716-1721;
6. (c) Martin, J.C.; Dvorak, C.A.; Smee, D.F.; Matthews, T.R.; Verheyden, J.P.H. 9-[(1,3-Dihydroxy-2-propoxy)methyl]guanine: A new potent and selective antiherpes agent. J. Med. Chem. 1983, 26(5), 759-761;
7. (d) Schaeffer, H.J. Nucleosides with antiviral activity. In Nucleosides, Nucleotides and their Biological Applications; Rideout, J.L., Henry, D.W., Beacham, L.M., Eds.; Academic Press: New York, 1983; 1-17.
8. (a) Cheng, Y.-C.; Huang, E.-S.; Lin, J.-C.; Mar, E.-C.; Pagano, J.S.; Dutschman, G.E.; Grill, S.P. Unique spectrum of activity of 9-[(1,3-dihydroxy-2- propoxy)methyl]-guanine against herpesviruses in vitro and its mode of action against herpes simplex virus type 1. Proc. Natl. Acad. Sci. U.S.A. 1983, 80(9), 2767-2770;
9. (b) Field, A.K.; Davies, M.E.; Dewitt, C.; Perry, H.C.; Liou, R.; Germerschausen, J.; Karkas, J.D.; Ashton, W.T.; Johnston, D.B.; Tolman, R.L. 9-{[2-Hydroxy-1 -(hydroxymethyl) ethoxy]methyl}guanine: A selective inhibitor of herpes group virus replication. Proc. Natl. Acad. Sci. U.S.A. 1983, 80(13), 4139-4143.
10. Smee, D.F.; Martin, J.C.; Verheyden, J.P.H.; Matthews, T.R. Anti-herpesvirus activity of the acyclic nucleoside 9-(1,3-dihydroxy-2- propoxymethyl)guanine. Antimicrob. Agents Chemother. 1983, 23(5), 676-682.
11. Holy, A.; Dvorakova, H.; Jindrich, J.; Masojidkova, M.; Budesinsky, M.; Balzarini, J.; Andrei, G.; De Clercq, E. Acyclic nucleotide analoges derived from 8-azapurines: Synthesis and antiviral activity. J. Med. Chem. 1996, 39, 4073-4088.
12. Balzarini, J.; Pannecouque, C.; De Clercq, E.; Aquaro, S.; Perno, C.-F.; Egberink, H.; Holy, A. Antiretrovirus activity of a novel class of acyclic pyrimidine nucleoside phosphonates. Antimicrob. Agents Chemother. 2002, 46, 2185-2193.
13. Balzarini, J.; Perno, C.F.; Schols, D.; De Clercq, E. Activity of acyclic nucleoside phosphonate analogues against human immunodeficiency virus in monocyteleoside macrophages and peripheral blood lymphocytes. Biochem. Biophys. Res. Commun. 1991, 178, 329-335.
14. De Clercq, E.; Holy, A.; Rosenberg, I.; Sakuma, T.; Balzarini, J.; Maudgal, P.C. A novel selective broad-spectrum anti-DNA virus agent. Nature 1986, 323, 464-467.
15. Naesens, L.; De Clercq, E.; Therapeutic potential of HPMPC (cidofovir), PMEA (adefovir) and related acyclic nucleoside phosphonate analogues as broad-spectrum antiviral agents. Nucleosides Nucleotides, 1997, 16, 983-992.
16. Balzarini, J.; Holy, A.; Jindrich, J.; Naesens, L.; Snoeck, R.; Schols, D.; De Clercq, E. Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: Potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2- phosphonomethoxypropyl)-2,6-diaminopurine. Antimicrob. Agents Chemother. 1993, 37, 332-338.
17. Balzarini, J.; Aquaro, S.; Perno, C.-F.; Holy, A.; De Clercq, E. Activity of the (R)-enantiomers of 9-(2-phosphonyl-methoxypropyl)adenine and 9-(2-phosphonyl-methoxypropyl)-2,6-diaminopurine against human immunodeficiency virus in different human cell systems. Biochem. Biophys. Res. Commun. 1996, 219, 337-341.
18. Holy, A. Phosphonylmethyl analogs of nucleotides and their derivatives: Chemistry and biology. Nucleosides Nucleotides, 1987, 6(1&2), 147-155.
19. Kim, C.U.; Luh, B.Y.; Misco, P.F.; Bronson, J.J.; Hitchcock, M.J.M.; Ghazzouli, I.; Martin, J.C. Acyclic purine phosphonate analogues as antiviral agents. Synthesis and structure-activity relationships. J. Med. Chem. 1990, 33, 1207-1213.
20. Jahne, G.; Kroha, H.; Muller, A.; Helsberg, M.; Winkler, I.; Gross, G.; Scholl, T. Regioselective synthesis and antiviral activity of purine nucleoside analogues with acyclic substituents at N7. Angew. Chem. Int. Ed. Engl. 1994, 33(5), 562-563.
21. Perbost, M.; Lucas, M.; Chavis, C.; Imbach, J.-L. Synthesis of racemic carboacyclonucleosides derived from butane-1,4-diol and hexane-1,6-diol. Nucleosides Nucleotides, 1992, 11(8), 1489-1505.
22. Perbost, M.; Lucas, M.; Chavis, C.; Imbach, J.-L. An expeditious synthesis of homochiral (R) 2-(9-purinyl)butane-1,4-diols from (S) butane-1,2,4-triol. Nucleosides Nucleotides 1992, 11(8), 1529-1537.
23. Jeffery, A.L.; Kim, J.-H.; Wiemer, D.F. Synthesis of acyclic nucleoside and nucleotide analogues from amino acids: A convenient approach to a PMEA-PMPA hybrid. Tetrahedron, 2000, 56, 5077-5083.
24. Giller, S.A.; Getsova, I.N.; Goncharova, I.N.; Petrulyanis, L.N.; Mironova, L.I.; Nazarova, G.F.; Bruk, E.I. Analogs of purine nucleosides and purine mono-and polynucleotides. II. Substituted α-(9-purinyl)-γ- butyrolactones. J. Org. Chem. U.S.S.R. 1974, 1477-1480.
25. (a) Freidich, W.; Bernhauer, K. Beitrage zur chemie und biochemie der "cobalamine," II. Mitteil.: Uber den abbau der "cobalamine" mit cer(III)-hydroxyd. 7-[D-ribofuranosido]-adenin, ein abbauprodukt des Pseudovitamins B12. Chem. Ber. 1956, 89, 2507-2512.
26. (b) Green, G.R.; Grinter, P.M.; Jarvest, R.L. The effect of the C-6 substituent on the regioselectivity of N-alkylation of 2-aminopurines. Tetrahedron 1990, 46, 6903-6914.
27. Boryski, J. Transglycosylation reactions of purine nucleosides. A review. Nucleoside Nucleotides 1996, 15(1-3), 771-791.
28. Kjellberg, J.; Johansson, N.G. Studies on the alkylation of derivatives of guanine. Nucleosides Nucleotides 1989, 8(2), 225-256.
29. (a) Montgomery, J.A.; Thomas, H.J. 7-Glycosylpurines. I. The synthesis of the anomeric 7-d-ribofuranosyladenines and the identification of the nucleoside from pseudovitamin B12. J. Amer. Chem. Soc. 1965, 87(23), 5442-5447.
30. (b) Montgomery, J.A.; Thomas, H.J. Directive influences in the preparation of purine nucleosides. J. Org. Chem. 1963, 28(9), 2304-2310.
31. Hakimelahi, G.H.; Ly, T.W.; Moosavi-Movahedi, A.A.; Jain, M.L.; Zakernia, H.D.; Mei, H.; Sambaiah, T.; Moshfegh, A.A.; Hakimelahi, S. Design, synthesis, and biological evaluation of novel nucleoside and nucleotide analogues as agents against DNA viruses and/or retroviruses. J. Med. Chem. 2001, 44(22), 3710-3720.
32. 6-[(dimethylamino)methylene]adenine bearing an active methylene group and their further derivatization leading to α-branched acyclic nucleoside analogues. Eur. J. Org. Chem. 1999, 2675-2682.
33. Okumura, K.; Oine, T.; Yamada, Y.; Tomie, M.; Adachi, T.; Nagura, T.; Kawazu, T.M.; Inoue, I. Synthetic studies on eritadenine. I. Reactions of some purines with the 2,3-O-protected dihydroxybutyrolactone. J. Org. Chem. 1971, 36(12), 1573-1579.
34. 7-isomer of adenosine. Collect. Czech. Chem. Commun. 1999, 64, 1316-1324.
35. Phillips, D.D. The reaction between diazoacetic ester and allylic halides. J. Amer. Chem. Soc. 1954, 76(21), 5385-5388.
36. Tisler, M.; Stanovik, B.; Zrimsek, Z. New synthetic approach for azolopurines and analogs. Heterocycles 1982, 17, 405-411.
37. (a) Hossain, N.; Rozenski, J.; De Clercq, E.; Herdewijn, P. Synthesis and antiviral activity of acyclic analogues of 1,5-anhydrohexitol nucleosides using mitsunobu reaction. Tetrahedron, 1996, 52(43), 13655-13670.
38. + analogues. Collect. Czech. Chem. Commun. 1997, 62, 948-956.
39. (a) Schaeffer, H.J.; Schwender, C.F. Enzyme inhibitors. 26. Bridging hydrophobic and hydrophilic regions on adenosine deaminase with some 9-(2-hydroxy-3-alkyl)adenines. J. Med. Chem. 1974, 17, 6-8.
40. (b) Baker, D.C.; Hawkins, L.D. Synthesis of inhibitors of adenosine deaminase. A total synthesis of erythro-3-(adenin-9-yl)-2-nonanol and its isomers from chiral precursors. J. Org. Chem. 1982, 47, 2179-2184.
41. Nishitani, T.; Iwasaki, T.; Mushika, Y.; Miyoshi, M. Synthesis of 2-(pyrimidin-1-yl)- and 2-(purin-9-yl)-2-amino acids. J. Org. Chem. 1979, 44, 2019-2023.
42. Holy, A. Syntheses of enantiomeric N-(3-hydroxy-2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases. Collect. Czech. Chem. Commun. 1993, 58, 649-674.
43. Holy, A.; Rosenberg, I. Synthesis of 9-(2-phosphonylmethoxyethyl)adenine and related compounds. Collect. Czech. Chem. Commun. 1987, 52, 2801-2809.
44. Hanessian, S.; Ugolini, A.; Dube, D.; Glamyan, A. Facile access to (S)-1,2,4-butanetriol and its derivatives. Can. J. Chem. 1984, 62, 2146-2147.