Synthesis of novel exocyclic amino nucleosides by parallel solid-phase combinatorial strategy

Tetrahedron

Volumn 59, Issue 13, 2003, Pages 2297-2307

  Varaprasad, Chamakura V ^a   Habib, Qazi ^a   Li, David Y ^a   Huang, Jingfan ^a   Abt, Jeffrey W ^a   Rong, Frank ^a   Hong, Zhi ^a   An, Haoyun ^a  

^a Ribapharm Inc   (United States)

Author keywords

Automated synthesis; Clitocine mimic; Exocyclic amino nucleoside; Library; Parallel solid phase combinatorial; Triazinyl

Indexed keywords

AMINONUCLEOSIDE; POLYSTYRENE; RESIN;

ARTICLE; PRIORITY JOURNAL; SYNTHESIS;

EID: 0037463758     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00211-4     Document Type: Article

References (68)

1. The estimation was made based on authors' personal data collection as well as the following websites: (a) http://www.fda.gov/cder/; (b) http://www.actis.org/; (c) http://merck.com/pubs/mmanual/; (d) http://www.pharmalicensing.com/.
2. The estimation was made based on authors' personal data collection as well as the following websites: (a) http://www.fda.gov/cder/; (b) http://www.actis.org/; (c) http://merck.com/pubs/mmanual/; (d) http://www.pharmalicensing.com/.
3. The estimation was made based on authors' personal data collection as well as the following websites: (a) http://www.fda.gov/cder/; (b) http://www.actis.org/; (c) http://merck.com/pubs/mmanual/; (d) http://www.pharmalicensing.com/.
4. The estimation was made based on authors' personal data collection as well as the following websites: (a) http://www.fda.gov/cder/; (b) http://www.actis.org/; (c) http://merck.com/pubs/mmanual/; (d) http://www.pharmalicensing.com/.
5. (a) Vorbruggen H., Ruh-Pohlenz C. The Handbook of Nucleoside Synthesis. 2001.
6. (b) Townsend L.B. Chemistry of Nucleosides and Nucleotides. Vol. 1:1988;Plenum, New York
7. (c) Townsend L.B. Chemistry of Nucleosides and Nucleotides. Vol. 2:1991;Plenum, New York
8. (d) Townsend L.B. Chemistry of Nucleosides and Nucleotides. Vol. 3:1994;Plenum, New York.
9. (a) See the following special issues: Chem. Rev. 1997, 92(2); Chem. Rev. 1996, 96(1); Acc. Chem. Res. 1996, 29(3). (b) Franzen R.G. J. Comb. Chem. 2:2000;195 (c) Andres C.J., Denhart D.J., Deshpande M.S., Gillman K.W. Comb. Chem. High Throughput Screening. 2:1999;191 (d) Kundu B., Khare S.K., Rastogi S.K. Prog. Drug Res. 53:1999;90 (e) Sofia M.J. Med. Chem. Res. 8:1998;362 (f) Houghten R.A., Pinilla C., Appel J.R., Blondelle S.E., Dooley C.T., Eichler J., Nefzi A., Ostresh J.M. J. Med. Chem. 42:1999;3743 (g) Rinnova M., Lebl M. Coll. Czech. Chem. Commun. 61:1996;171 (h) Stankova M., Lebl M. Mol. Div. 2:1996;75.
10. (a) See the following special issues: Chem. Rev. 1997, 92(2); Chem. Rev. 1996, 96(1); Acc. Chem. Res. 1996, 29(3). (b) Franzen R.G. J. Comb. Chem. 2:2000;195 (c) Andres C.J., Denhart D.J., Deshpande M.S., Gillman K.W. Comb. Chem. High Throughput Screening. 2:1999;191 (d) Kundu B., Khare S.K., Rastogi S.K. Prog. Drug Res. 53:1999;90 (e) Sofia M.J. Med. Chem. Res. 8:1998;362 (f) Houghten R.A., Pinilla C., Appel J.R., Blondelle S.E., Dooley C.T., Eichler J., Nefzi A., Ostresh J.M. J. Med. Chem. 42:1999;3743 (g) Rinnova M., Lebl M. Coll. Czech. Chem. Commun. 61:1996;171 (h) Stankova M., Lebl M. Mol. Div. 2:1996;75.
11. (a) See the following special issues: Chem. Rev. 1997, 92(2); Chem. Rev. 1996, 96(1); Acc. Chem. Res. 1996, 29(3). (b) Franzen R.G. J. Comb. Chem. 2:2000;195 (c) Andres C.J., Denhart D.J., Deshpande M.S., Gillman K.W. Comb. Chem. High Throughput Screening. 2:1999;191 (d) Kundu B., Khare S.K., Rastogi S.K. Prog. Drug Res. 53:1999;90 (e) Sofia M.J. Med. Chem. Res. 8:1998;362 (f) Houghten R.A., Pinilla C., Appel J.R., Blondelle S.E., Dooley C.T., Eichler J., Nefzi A., Ostresh J.M. J. Med. Chem. 42:1999;3743 (g) Rinnova M., Lebl M. Coll. Czech. Chem. Commun. 61:1996;171 (h) Stankova M., Lebl M. Mol. Div. 2:1996;75.
12. (a) See the following special issues: Chem. Rev. 1997, 92(2); Chem. Rev. 1996, 96(1); Acc. Chem. Res. 1996, 29(3). (b) Franzen R.G. J. Comb. Chem. 2:2000;195 (c) Andres C.J., Denhart D.J., Deshpande M.S., Gillman K.W. Comb. Chem. High Throughput Screening. 2:1999;191 (d) Kundu B., Khare S.K., Rastogi S.K. Prog. Drug Res. 53:1999;90 (e) Sofia M.J. Med. Chem. Res. 8:1998;362 (f) Houghten R.A., Pinilla C., Appel J.R., Blondelle S.E., Dooley C.T., Eichler J., Nefzi A., Ostresh J.M. J. Med. Chem. 42:1999;3743 (g) Rinnova M., Lebl M. Coll. Czech. Chem. Commun. 61:1996;171 (h) Stankova M., Lebl M. Mol. Div. 2:1996;75.
13. (a) See the following special issues: Chem. Rev. 1997, 92(2); Chem. Rev. 1996, 96(1); Acc. Chem. Res. 1996, 29(3). (b) Franzen R.G. J. Comb. Chem. 2:2000;195 (c) Andres C.J., Denhart D.J., Deshpande M.S., Gillman K.W. Comb. Chem. High Throughput Screening. 2:1999;191 (d) Kundu B., Khare S.K., Rastogi S.K. Prog. Drug Res. 53:1999;90 (e) Sofia M.J. Med. Chem. Res. 8:1998;362 (f) Houghten R.A., Pinilla C., Appel J.R., Blondelle S.E., Dooley C.T., Eichler J., Nefzi A., Ostresh J.M. J. Med. Chem. 42:1999;3743 (g) Rinnova M., Lebl M. Coll. Czech. Chem. Commun. 61:1996;171 (h) Stankova M., Lebl M. Mol. Div. 2:1996;75.
14. (a) See the following special issues: Chem. Rev. 1997, 92(2); Chem. Rev. 1996, 96(1); Acc. Chem. Res. 1996, 29(3). (b) Franzen R.G. J. Comb. Chem. 2:2000;195 (c) Andres C.J., Denhart D.J., Deshpande M.S., Gillman K.W. Comb. Chem. High Throughput Screening. 2:1999;191 (d) Kundu B., Khare S.K., Rastogi S.K. Prog. Drug Res. 53:1999;90 (e) Sofia M.J. Med. Chem. Res. 8:1998;362 (f) Houghten R.A., Pinilla C., Appel J.R., Blondelle S.E., Dooley C.T., Eichler J., Nefzi A., Ostresh J.M. J. Med. Chem. 42:1999;3743 (g) Rinnova M., Lebl M. Coll. Czech. Chem. Commun. 61:1996;171 (h) Stankova M., Lebl M. Mol. Div. 2:1996;75.
15. (a) See the following special issues: Chem. Rev. 1997, 92(2); Chem. Rev. 1996, 96(1); Acc. Chem. Res. 1996, 29(3). (b) Franzen R.G. J. Comb. Chem. 2:2000;195 (c) Andres C.J., Denhart D.J., Deshpande M.S., Gillman K.W. Comb. Chem. High Throughput Screening. 2:1999;191 (d) Kundu B., Khare S.K., Rastogi S.K. Prog. Drug Res. 53:1999;90 (e) Sofia M.J. Med. Chem. Res. 8:1998;362 (f) Houghten R.A., Pinilla C., Appel J.R., Blondelle S.E., Dooley C.T., Eichler J., Nefzi A., Ostresh J.M. J. Med. Chem. 42:1999;3743 (g) Rinnova M., Lebl M. Coll. Czech. Chem. Commun. 61:1996;171 (h) Stankova M., Lebl M. Mol. Div. 2:1996;75.
16. (a) See the following special issues: Chem. Rev. 1997, 92(2); Chem. Rev. 1996, 96(1); Acc. Chem. Res. 1996, 29(3). (b) Franzen R.G. J. Comb. Chem. 2:2000;195 (c) Andres C.J., Denhart D.J., Deshpande M.S., Gillman K.W. Comb. Chem. High Throughput Screening. 2:1999;191 (d) Kundu B., Khare S.K., Rastogi S.K. Prog. Drug Res. 53:1999;90 (e) Sofia M.J. Med. Chem. Res. 8:1998;362 (f) Houghten R.A., Pinilla C., Appel J.R., Blondelle S.E., Dooley C.T., Eichler J., Nefzi A., Ostresh J.M. J. Med. Chem. 42:1999;3743 (g) Rinnova M., Lebl M. Coll. Czech. Chem. Commun. 61:1996;171 (h) Stankova M., Lebl M. Mol. Div. 2:1996;75.
17. (a) See the following special issues: Chem. Rev. 1997, 92(2); Chem. Rev. 1996, 96(1); Acc. Chem. Res. 1996, 29(3). (b) Franzen R.G. J. Comb. Chem. 2:2000;195 (c) Andres C.J., Denhart D.J., Deshpande M.S., Gillman K.W. Comb. Chem. High Throughput Screening. 2:1999;191 (d) Kundu B., Khare S.K., Rastogi S.K. Prog. Drug Res. 53:1999;90 (e) Sofia M.J. Med. Chem. Res. 8:1998;362 (f) Houghten R.A., Pinilla C., Appel J.R., Blondelle S.E., Dooley C.T., Eichler J., Nefzi A., Ostresh J.M. J. Med. Chem. 42:1999;3743 (g) Rinnova M., Lebl M. Coll. Czech. Chem. Commun. 61:1996;171 (h) Stankova M., Lebl M. Mol. Div. 2:1996;75.
18. (a) See the following special issues: Chem. Rev. 1997, 92(2); Chem. Rev. 1996, 96(1); Acc. Chem. Res. 1996, 29(3). (b) Franzen R.G. J. Comb. Chem. 2:2000;195 (c) Andres C.J., Denhart D.J., Deshpande M.S., Gillman K.W. Comb. Chem. High Throughput Screening. 2:1999;191 (d) Kundu B., Khare S.K., Rastogi S.K. Prog. Drug Res. 53:1999;90 (e) Sofia M.J. Med. Chem. Res. 8:1998;362 (f) Houghten R.A., Pinilla C., Appel J.R., Blondelle S.E., Dooley C.T., Eichler J., Nefzi A., Ostresh J.M. J. Med. Chem. 42:1999;3743 (g) Rinnova M., Lebl M. Coll. Czech. Chem. Commun. 61:1996;171 (h) Stankova M., Lebl M. Mol. Div. 2:1996;75.
19. (a) An H., Cook P.D. Chem. Rev. 100:2000;3311.
20. (b) An H., Cummins L.L., Griffey R.H., Bharadwaj R., Haly B.D., Fraser A.S., Wilson-Lingardo L., Risen L.M., Wyatt J.R., Cook P.D. J. Am. Chem. Soc. 119:1997;3696.
21. (c) Barvian M.R. Chemtracts - Org. Chem. 11:1998;639.
22. (d) Merritt A.T. Comb. Chem. High Throughput Screening. 1:1998;57.
23. (a) Gravert D.J., Janda K.D. Chem. Rev. 97:1997;489.
24. (b) Sieber F., Wentworth P. Jr., Toker J.D., Wentworth A.D., Metz W.A., Reed N.N., Janda K.D. J. Org. Chem. 64:1999;5188 (c) Reed N.N., Janda K.D. Org. Lett. 2:2000;1311.
25. (c) Reed N.N., Janda K.D. Org. Lett. 2:2000;1311.
26. (a) Nakamura H., Linclau B., Curran D.P. J. Am. Chem. Soc. 123:2001;10119.
27. (b) Luo Z.Y., Zhang Q.S., Oderaotoshi Y., Curran D.P. Science. 291:2001;1766.
28. (c) Studer A., Hadida S., Ferritto R., Kim S.Y., Jeger P., Wipf P., Curran D.P. Science. 275:1997;823.
29. (d) Studer A., Jeger P., Wipf P., Curran D.P. J. Org. Chem. 62:1997;2917.
30. (a) Zhou W.-Q., Roland A., Jin Y., Iyer R.P. Tetrahedron Lett. 41:2000;441.
31. (b) Jin Y., Chen X.-L., Cote M.-E., Roland A., Korba B., Mounir S., Iyer R.P. Bioorg. Med. Chem. Lett. 11:2001;2057.
32. (c) Jin Y., Roland A., Zhou W.-Q., Fauchon M., Lyaku J., Iyer R.P. Bioorg. Med. Chem. Lett. 10:2000;1921.
33. (a) Beaucage S.L., Iyer R.P. Tetrahedron. 48:1992;2223-2311.
34. (b) Beaucage, S. L. Methods Mol. Biol. (Totowa, N. J.) 1993, 20(Protocols for Oligonucleotides and Analogs), 33.
35. (a) Atkinson T., Smith M. Gait M.J. Oligonucleotide Synthesis, A Practical Approach. 1990;35-81 IRL
36. (b) Sproat B., Gait M.J. Gait M.J. Oligonucleotide Synthesis, A Practical Approach. 1990;83-115 IRL.
37. (a) Link A., van Calenbergh S., Herdewijn P. Tetrahedron Lett. 39:1998;5175.
38. (b) van Calenbergh S., Link A., Fujikawa S., de Ligt R.A.F., Vanheusden V., Golisade A., Blaton N.M., Razenski J., Ijzerman A.P., Herdewijn P. J. Med. Chem. 45:2002;1845.
39. (a) Ferrero M., Gotor V. Chem. Rev. 100:2000;4319.
40. (b) Ichikawa E., Kato K. Curr. Med. Chem. 8:2001;385.
41. (c) Pathak T. Chem. Rev. 102:2002;1623.
42. (a) Miles R.W., Samano V., Robins M.J. J. Am. Chem. Soc. 117:1995;5951.
43. (b) De Clercq E., Balzarini J., Madej D., Hansske F., Robins M.J. J. Med. Chem. 30:1987;481.
44. (c) Riley T.A., Larson S.B., Avery T.L., Finch R.A., Robins R.K. J. Med. Chem. 33:1990;572.
45. (d) Riley T.A., Larson S.B., Avery T.L., Finch R.A., Robins R.K. J. Med. Chem. 33:1990;572.
46. (e) Girgis N.S., Micheal M.A., Smee D.F., Alaghamandan H.A., Robins R.K. J. Med. Chem. 33:1990;2750.
47. (f) Harada H., Asano O., Hoshino Y., Yoshikawa S., Matsukura M., Kabasawa Y., Niijima J., Kotake Y., Watanabe N., Kawata T., Inoue T., Horizoe T., Yasuda N., Minami H., Nagata K., Murakami M., Nagaoka J., Kobayashi S., Tanaka I., Abe S. J. Med. Chem. 44:2001;170.
48. Kubo I., Kim M., Wood W.F., Naoki H. Tetrahedron Lett. 27:1986;4277.
49. (a) Moss R.J., Petrie C.R., Meyer R.B. Jr., Nord L.D., Willis R.C., Smith R.A., Larson S.B., Kini G.D., Robins R.K. J. Med. Chem. 31:1988;786.
50. (b) Larson S.B., Moss R.J., Kini G.D., Robins R.K. Acta Crystallogr. C44:1988;1076
51. (c) Kamikawa T., Fujie S., Yamagiwa Y., Kim M., Kawaguchi H. J. Chem. Soc., Chem. Commun. 1988;195.
52. (a) Berman H.M., Rousseau R.J., Mancuso R.W., Kreishman G.P., Robins R.K. Tetrahedron Lett. 1973;3099.
53. (b) Ghose A.K., Viswanadhan V.N., Sanghvi Y.S., Nord L.D., Willis R.C., Revankar G.R., Robins R.K. Proc. Natl Acad. Sci. USA. 86:1989;8242.
54. Townsend L.B., Robins R.K. J. Am. Chem. Soc. 85:1963;242.
55. (a) Whitten J.P., Xie Y.F., Erickson P.E., Webb T.R., De Souza E.B., Grigoriadis D.E., McCarthy J.R. J. Med. Chem. 39:1996;4354.
56. (b) Gustafson G.R., Baldino C.M., O'Donnell M.-M.E., Sheldon A., Tarsa R.J., Veni C.J., Coffen D.L. Tetrahedron. 54:1998;4501.
57. (c) Hajduk P.J., Dinges J., Schkeryantz J.M., Janowick D., Kaminski M., Tufano M., Augeri D.J., Petros A., Nienaber V., Zhong P., Hammond R., Coen M., Beutel B., Katz L., Fesik S.W. J. Med. Chem. 42:1999;3852.
58. 'Successful rate' for a plate of 96 compounds was defined as the percentage of the library members with more than 60% LC-MS purity comparing with all 96 compounds in the plate. Therefore, it represents the quality of a plate synthesized. Library members with more than 60% LC-MS purity are registered to database for the biological screening to reduce false-positive and false-negative results. The higher of the successful rate is, the higher quality of the plate has.
59. (a) Yan B., Nguyen N., Liu L., Holland G., Raju B. J. Comb. Chem. 2:2000;66.
60. (b) Booth S., Hermkens P.H.H., Ottenheijm H.C.J., Rees D.C. Tetrahedron. 54:1998;15385.
61. (c) Hermkens P.H.H., Ottenheijm H.C.J., Rees D.C. Tetrahedron. 53:1997;5643.
62. (d) Hermkens P.H.H., Ottenheijm H.C.J., Rees D.C. Tetrahedron. 52:1996;4527.
63. Choo H., Chong Y., Chu C.K. Org. Lett. 3:2001;1471.
64. Crimmins M.T., Zuercher W.J. Org. Lett. 2:2000;1065.
65. Bressi J.C., Choe J., Hough M.T., Buckner F.S., Van Voorhis W.C., Verlinde C.L.M.J., Hol W.G.J., Gelb M.H. J. Med. Chem. 43:2000;4135.
66. Stimac A., Kobe J. Carbohydr. Res. 324:2000;149.
67. Stimac A., Kobe J. Carbohydr. Res. 232:1992;359.
68. Logue M.W., Han B.H. Carbohydr. Res. 121:1983;287.