Recent advances in the synthesis of purine derivatives and their precursors

Tetrahedron

Volumn 64, Issue 37, 2008, Pages 8585-8603

  Legraverend, Michel ^a  

^a INSTITUT CURIE   (France)

Author keywords

ATP analogues; Enzyme inhibitors; Purine chemistry; Purine libraries; Receptor antagonists

Indexed keywords

6 ARYLSULFONYL 3',5' BIS O (TERT BUTYL DIMETHYLSILYL) 2' DEOXYGUANOSINE; ADENINE; ADENINE DERIVATIVE; ADENOSINE RECEPTOR BLOCKING AGENT; ADENOSINE TRIPHOSPHATE DERIVATIVE; ALCOHOL DERIVATIVE; ALKANE; ARYLSULFONIC ACID DERIVATIVE; BRONCHODILATING AGENT; CVT 5440; CYCLIN DEPENDENT KINASE 1 INHIBITOR; CYCLIN DEPENDENT KINASE 2 INHIBITOR; DEOXYRIBOSE; GUANOSINE; HEAT SHOCK PROTEIN 90 INHIBITOR; NUCLEOSIDE DERIVATIVE; PHOSPHODIESTERASE INHIBITOR; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PURINE DERIVATIVE; PYRIMIDINE; PYRIMIDINE DERIVATIVE; THIAZOLE DERIVATIVE; URACIL DERIVATIVE; XANTHINE DERIVATIVE;

ALKYLATION; ARYLATION; COMBINATORIAL CHEMISTRY; DERIVATIZATION; DRUG POTENCY; DRUG SYNTHESIS; MICHAEL ADDITION; MITSUNOBU REACTION; NUCLEIC ACID SYNTHESIS; PRIORITY JOURNAL; REVIEW; SOLID PHASE SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; TRAUBE SYNTHESIS;

EID: 48149098365     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.115     Document Type: Review

References (91)

1. Rosemeyer H. Chem. Biodivers. 1 (2004) 361-401
2. Legraverend M., and Grierson D.S. Bioorg. Med. Chem. 14 (2006) 3987-4006
3. Schmidt A.P., Lara D.R., and Souza D.O. Pharmacol. Ther. 116 (2007) 401-416
4. Ertl P., Jelfs S., Mühlbacher J., Schuffenhauer A., and Selzer P. J. Med. Chem. 49 (2006) 4568-4573
5. Wan Z.-K., Binnun E., Wilson D.P., and Lee J. Org. Lett. 7 (2005) 5877-5880
6. Lakshman M.K., Gunda P., and Pradhan P. J. Org. Chem. 70 (2005) 10329-10335
7. Lakshman M.K., Hilmer J.H., Martin J.Q., Keeler J.C., Dinh Y.Q.V., Ngassa F.N., and Russon L.M. J. Am. Chem. Soc. 123 (2001) 7779-7787
8. Havelkova M., Dvorak D., and Hocek M. Synthesis (2001) 1704-1710
9. Capek P., Vrábel M., Hasník Z., Pohl R., and Hocek M. Synthesis (2006) 3515-3526
10. Hocek M., Naus P., Pohl R., Votruba I., Furman P.A., Tharnish P.M., and Otto M.J. J. Med. Chem. 48 (2005) 5869-5873
11. Bakkestuen A.K., Gundersen L.-L., Langli G., Liu F., and Nolsoe J.M.J. Bioorg. Med. Chem. Lett. 10 (2000) 1207-1210
12. Chang Y.T., Gray N.S., Rosania G.R., Sutherlin D.P., Kwon S., Norman T.C., Sarohia R., Leost M., Meijer L., and Schultz P.G. Chem. Biol. 6 (1999) 361-375
13. Chapman E., Best M.D., Hanson S.R., and Wong C.-H. Angew. Chem., Int. Ed. 43 (2004) 3526-3548
14. Krystof V., Lenobel R., Havlicek L., Kuzma M., and Strnad M. Bioorg. Med. Chem. Lett. 12 (2002) 3283-3286
15. Moravec J., Krystof V., Hanus J., Havlicek L., Moravcova D., Fuksova K., Kuzma M., Lenobel R., Otyepka M., and Strnad M. Bioorg. Med. Chem. Lett. 13 (2003) 2993-2996
16. Legraverend M., Ludwig O., Leclerc S., and Meijer L. J. Heterocycl. Chem. 38 (2001) 299-303
17. Legraverend M., Tunnah P., Noble M., Ducrot P., Ludwig O., Grierson D.S., Leost M., Meijer L., and Endicott J. J. Med. Chem. 43 (2000) 1282-1292
18. Chang Y.-T., Choi G., Bae Y.-S., Burdett M., Moon H.-S., Lee J.W., Gray N.S., Schultz P.G., Meijer L., Chung S.-K., Choi K.Y., Suh P.-G., and Ryu S.H. ChemBioChem (2002) 897-901
19. Legraverend M., Ludwig O., Bisagni E., Leclerc S., Meijer L., Giocanti N., Sadri R., and Favaudon V. Bioorg. Med. Chem. 7 (1999) 1281-1293
20. Nugiel D.A., Cornelius L.A.M., and Corbett J.W. J. Org. Chem. 62 (1997) 201-203
21. Piguel S., and Legraverend M. J. Org. Chem. 72 (2007) 7026-7029
22. Elphick L.M., Lee S.E., Gouverneur V., and Mann D.J. ACS Chem. Biol. 2 (2007) 299-314
23. Gibson A.E., Arris C.E., Bentley J., Boyle F.T., Curtin N.J., Davies T.G., Endicott J.A., Golding B.T., Grant S., Griffin R.J., Jewsbury P., Johnson L.N., Veronique Mesguiche V., Newell D.R., Noble M.E.M., Julie A., Tucker J.A., and Whitfield H.J. J. Med. Chem. 45 (2002) 3381-3393
24. Hardcastle I.R., Ian R., Arris C.E., Bentley J., Boyle F.T., Chen Y., Curtin N.J., Endicott J.A., Gibson A.E., Golding B.T., Griffin R.J., Jewsbury P., Menyerol J., Mesguiche V., Newell D.R., Noble M.E.M., Pratt D.J., Wang L.-Z., and Whitfield H.J. J. Med. Chem. 47 (2004) 3710-3722
25. Huang L.-K., Cherng Y.-C., Cheng Y.-R., Jang J.-P., Chao Y.-L., and Cherng Y.-J. Tetrahedron 63 (2007) 5323-5327
26. Liu J., and Robins M.J. J. Am. Chem. Soc. 129 (2007) 5962-5968
27. Zhong M., and Robins M.J. J. Org. Chem. 71 (2006) 8901-8906
28. Zhong M., Nowak I., Cannon J.F., and Robins M.J. J. Org. Chem. 71 (2006) 4216-4221
29. Zhong M., Nowak I., and Robins M.J. J. Org. Chem. 71 (2006) 7773-7779
30. Khalafi-Nezhad A., Zarea A., Soltani Rad M.N., Mokhtari B., and Parhami A. Synthesis (2005) 419-424
31. Fu H., and Lam Y. J. Comb. Chem. 7 (2005) 734-738
32. Qu G.-R., Zhang Z.-G., Geng M.-W., Xia R., Zhao L., and Guo H.-M. Synlett (2007) 0721-0724
33. Lam P.Y.S., Clark C.G., Saubern S., Adams J., Averill K.M., Chan D.M.T., and Combs A. Synlett (2000) 674-676
34. Strieter E.R., Blackmond D.G., and Buchwald S.L. J. Am. Chem. Soc. 127 (2005) 4120-4121
35. Moriarty K.J., Koblish H.K., Garrabrant T., Maisuria J., Khalil E., Ali F., Petrounia I.P., Crysler C.S., Maroney A.C., Johnson D.L., Galemmo J., and Robert A. Bioorg. Med. Chem. Lett. 16 (2006) 5778-5783
36. Ding S., Gray N.S., Ding Q., and Schultz P.G. Tetrahedron Lett. 42 (2001) 8751-8755
37. Bakkestuen A.K., and Gundersen L.-L. Tetrahedron Lett. 44 (2003) 3359-3362
38. Jacobsen M.F., Knudsen M.M., and Gothelf K.V. J. Org. Chem. 71 (2006) 9183-9190
39. Jenny T.F., Previsani N., and Benner S.A. Tetrahedron Lett. 32 (1991) 7029-7032
40. Peterson M.L., and Vince R. J. Med. Chem. 34 (1991) 2787-2797
41. Wachtmeister J., Classohn B., and Samuelsson B. Tetrahedron 51 (1995) 2029-2038
42. Wang P., Schinazi R., and Chu C.K. Bioorg. Med. Chem. Lett. 8 (1998) 1585-1588
43. Jacobson K.A., Ji X.-D., Li A.-H., Melman N., Siddiqui M.A., Shin K.-J., Marquez V.E., and Ravi R.G. J. Med. Chem. 43 (2000) 2196-2203
44. Nandanan E., Jang S.-Y., Moro S., Kim H.O., Siddiqui M.A., Russ P., Marquez V.E., Busson R., Herdewijn P., Harden T.K., Boyer J.L., and Jacobson K.A. J. Med. Chem. 43 (2000) 829-842
45. Gray N.S., Kwon S., and Schultz P.G. Tetrahedron Lett. 38 (1997) 1161-1164
46. Toyota A., Katagiri N., and Kaneko C. Heterocycles 36 (1993) 1625-1630
47. Lu W., Sengupta S., Petersen J.L., Akhmedov N.G., and Shi X. J. Org. Chem. 72 (2007) 5012-5015
48. Legraverend M., Boumchita H., and Bisagni E. Synthesis (1990) 587-589
49. Daluge S.M., Martin M.T., Sickles B.R., and Livingston D.A. Nucleosides Nucleotides Nucleic Acids 19 (2000) 297-327
50. He R., Ching S.M., and Lam Y. J. Comb. Chem. 8 (2006) 923-928
51. Allwood M.B., Cannan B., van Aalten D.M.F., and Eggleston I.M. Tetrahedron 63 (2007) 12294-12302
52. Zhang L., and Zhang Y.J. Tetrahedron Lett. 47 (2006) 775-778
53. van den Berg D., Zoellner K.R., Ogunrombi M.O., Malan S.F., Terre′Blanche G., Castagnoli Jr. N., Bergh J.J., and Petzer J.P. Bioorg. Med. Chem. 15 (2007) 3692-3702
54. Kalla R.V., Elzein E., Perry T., Li X., Gimbel A., Yang M., Zeng D., and Zablocki J. Bioorg. Med. Chem. Lett. 18 (2008) 1397-1401
55. Elzein E., Kalla R., Li X., Perry T., Parkhill E., Palle V., Varkhedkar V., Gimbel A., Zeng D., and Lustig D. Bioorg. Med. Chem. Lett. 16 (2006) 302-306
56. Varani K., Gessi S., Merighi S., Vincenzi F., Cattabriga E., Benini A., Klotz K.-N., Baraldi P.G., Tabrizi M.A., and Lennan S.M. Biochem. Pharmacol. 70 (2005) 1601-1612
57. Zablocki J., Kalla R., Perry T., Palle V., Varkhedkar V., Xiao D., Piscopio A., Maa T., Gimbel A., and Hao J. Bioorg. Med. Chem. Lett. 15 (2005) 609-612
58. Kazaoka K., Sajiki H., and Hirota K. Chem. Pharm. Bull. 51 (2003) 608-611
59. Ahn H.-S., Bercovici A., Boykow G., Bronnenkant A., Chackalamannil S., Chow J., Cleven R., Cook J., Czarniecki M., Domalski C., Fawzi A., Green M., Gündes A., Ho G., Laudicina M., Lindo N., Ma K., Manna M., McKittrick B., Mirzai B., Nechuta T., Neustadt B., Puchalski C., Pula K., Silverman L., Smith E., Stamford A., Tedesco R.P., Tsai H., Tulshian D.B., Vaccaro H., Watkins R.W., Weng X., Witkowski J.T., Xia Y., and Zhang H. J. Med. Chem. 40 (1997) 2196-2210
60. Boyle C.D., Xu R., Asberom T., Chackalamannil S., Clader J.W., Greenlee W.J., Guzik H., Hu Y., Hu Z., Lankin C.M., Pissarnitski D.A., Stamford A.W., Wang Y., Skell J., Kurowski S., Vemulapalli S., Palamanda J., Chintala M., Wu P., Myers J., and Wang P. Bioorg. Med. Chem. Lett. 15 (2005) 2365-2369
61. Brown D.J., and Mason S.F. The Pyrimidines. In: Sons J.W. (Ed). The Chemistry of Heterocyclic Compounds (1962), Interscience, New York, NY, London 31-81
62. Baindur N., Chadha N., and Player M.R. J. Comb. Chem. 5 (2003) 653-659
63. Kenner G.W., Lythgoe B., Todd A.R., and Topham A. J. Chem. Soc. (1943) 388-390
64. Taddei D., Slawin A.M.Z., and Woollins J.D. Eur. J. Org. Chem. (2005) 939-947
65. Marchetti F., Sayle K.L., Bentley J., Clegg W., Curtin N.J., Endicott J.A., Golding B.T., Griffin R.J., Haggerty K., Harrington R.W., Mesguiche V., Newell D.R., Noble M.E.M., Parsons R.J., Pratt D.J., Wang L.Z., and Hardcastle I.R. Org. Biomol. Chem. 5 (2007) 1577-1585
66. Gibson C.L., La Rosa S., and Suckling C.J. Org. Biomol. Chem. 1 (2003) 1909-1918
67. Sayle K.L., Bentley J., Boyle F.T., Calvert A.H., Cheng Y., Curtin N.J., Endicott J.A., Golding B.T., Hardcastle I.R., and Jewsbury P. Bioorg. Med. Chem. Lett. 13 (2003) 3079-3082
68. Harnden M.R., and Hurst D. Aust. J. Chem. 42 (1990) 55-62
69. Albert A., Brown D.J., and Wood H.C.S. J. Chem. Soc. (1954) 3832-3839
70. Brown D.J., and Jacobsen N.W. J. Chem. Soc., Perkin Trans. 1 (1965) 3770-3778
71. Yang J., Dang Q., Liu J., Wei Z., Wu J., and Bai X. J. Comb. Chem. 7 (2005) 474-482
72. Hammarstrom L.G.J., Meyer M.E., Smith D.B., and Talamas F.X. Tetrahedron Lett. 44 (2003) 8361-8363
73. Hammarstrom L.G.J., Smith D.B., Talamas F.X., Labadie S.S., and Krauss N.E. Tetrahedron Lett. 43 (2002) 8071-8073
74. Liu J., Dang Q., Wei Z., Zhang H., and Bai X. J. Comb. Chem. 7 (2005) 627-636
75. Hammarstrom L.G.J., Smith D.B., and Talamas F.X. Tetrahedron Lett. 48 (2007) 2823-2827
76. Trivedi B.K., and Bruns R.F. J. Med. Chem. 32 (1989) 1667-1673
77. Ding S., Gray N.S., Ding Q., Wu X., and Schultz P.G. J. Comb. Chem. 4 (2002) 183-186
78. Whitfield H.J., Griffin R.J., Hardcastle I.R., Henderson A., Meneyrol J., Mesguiche V., Sayle K.L., and Golding B.T. Chem. Commun. (2003) 2802-2803
79. Gangjee A., Jain H.D., and Kisliuk R.L. Bioorg. Med. Chem. Lett. 15 (2005) 2225-2230
80. Arnold L.D., Calderwood D.J., Dixon R.W., Johnston D.N., Kamens J.S., Munschauer R., Rafferty P., and Ratnofsky S.E. Bioorg. Med. Chem. Lett. 10 (2000) 2167-2170
81. Chien T.-C., Meade E.A., Hinkley J.M., and Townsend L.B. Org. Lett. 6 (2004) 2857-2859
82. Gangjee A., Mavandadi F., Kisliuk R.L., McGuire J.J., and Queener S.F. J. Med. Chem. 39 (1996) 4563-4568
83. Gangjee A., Yang J., McGuireb J.J., and Kisliuk R.L. Bioorg. Med. Chem. 14 (2006) 8590-8598
84. Legraverend M., Ngongo-Tekam R.M., Bisagni E., and Zerial A. J. Med. Chem. 28 (1985) 1477-1480
85. Biamonte M.A., Shi J., Hong K., Hurst D.C., Zhang L., Fan J., Busch D.J., Karjian P.L., Maldonado A.A., Sensintaffar J.L., Yang Y.-C., Kamal A., Lough R.E., Lundgren K., Burrows F.J., Timony G.A., Boehm M.F., and Kasibhatla S.R. J. Med. Chem. 49 (2006) 817-828
86. Llauger L., He H., Kim J., Aguirre J., Rosen N., Peters U., Davies P., and Chiosis G. J. Med. Chem. 48 (2005) 2892-2905
87. Müller C.E., Shi D., Manning J., Malcolm, and Daly J.W. J. Med. Chem. 36 (1993) 3341-3349
88. 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., and Abe S. J. Med. Chem. 44 (2001) 170-179
89. Liu J., Dang Q., Wei Z., Shi F., and Bai X. J. Comb. Chem. 8 (2006) 410-416
90. Liu J., Patch R.J., Schubert C., and Player M.R. J. Org. Chem. 70 (2005) 10194-10197
91. Horton D.A., Bourne G.T., and Smythe M.L. Chem. Rev. 103 (2003) 893-930