An efficient copper-catalyzed microwave-assisted S-arylation towards the synthesis of 8-arylsulfanyl adenines

Synlett

Volumn , Issue 20, 2011, Pages 3008-3012

  Sun, Weilin ^a   Patel, Pallav D ^b   Stephani, Ralph A ^b   Chiosis, Gabriela ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b ST JOHN'S UNIVERSITY   (United States)

Author keywords

copper catalyzed S arylation; microwave; phase transfer catalyst

Indexed keywords

8 ARYLSULFANYL ADENINE DERIVATIVE; ADENINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COUPLING FACTOR; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICROWAVE RADIATION; NUCLEOPHILICITY; REACTION TIME; SYNTHESIS;

EID: 82955235587     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1289888     Document Type: Article

References (54)

1. Hartwig J F., In Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1 Negishi E Wiley-Interscience New York 2002 1051
2. Muci A R., Buchwald S L., Top. Curr. Chem. 2002 219 131
3. Prim D, Campagne J.-M, Joseph D, Andrioletti B, Tetrahedron 2002 58 2041
4. Kondo T, Mitsudo T.-A, Chem. Rev. 2000 100 3205
5. Hartwig J F., Acc. Chem. Res. 1998 31 852
6. Beletskaya I P., Ananikov V P., Eur. J. Org. Chem. 2007 3431
7. For general reviews on sulfides, see: Comprehensi v e Organic Chemistry Vol. 3 Jones D N. Pergamon Press Oxford 1979
8. He H, Zatorska D, Kim J, Aguirre J, Llauger L, She Y, Wu N, Immormino R M., Gewirth D T., Chiosis G, J. Med. Chem. 2006 49 381
9. Chiosis G, Timaul M N., Lucas B, Munster P N., Zheng F F., Sepp-Lorenzino L, Rosen N A., Chem. Biol. 2001 8 289
10. Wang Y, Chackalamannil S, Hu Z, Clader J W., Greenlee W, Billard W, Binch H, Crosby G, Ruperto V, Duffy R A., McQuade R, Lachowicz J E., Bioorg. Med. Chem. Lett. 2000 10 2247
11. Nielsen S F., Nielsen E O., Olsen G M., Liljefors T, Peters D, J. Med. Chem. 2000 43 2217
12. DeMartino G, Edler M C., LaRegina G, Cosuccia A, Barbera M C., Barrow D, Nicholson R I., Chiosis G, Brancale A, Hamel E, Artico M, Silvestri R, J. Med. Chem. 2006 49 947
13. Kadlor S W., Kalish V J., Davies J F., Shetty B V., Fritz J E., Appelt K, Burgess J A., Campanale K M., Chirgadze N Y., Clawson D K., Dressman B A., Hatch S D., Khalil D A., Kosa M B., Lubbehusen P P., Muesing M A., Patick A K., Reich S H., Su K S., Tatlock J H., J. Med. Chem. 1997 40 3979
14. Marcincal-Letebvre A, Gesquiere C, Lemer C, Dupuis B, J. Med. Chem. 1981 24 889
15. Liu G, Link J T., Pei Z, Reilly E B., Leitza S, Nguyen B, Marsh K C., Okasinski G F., vonGeldem T W., Ormes M, Fowler K, Gallatin M, J. Med. Chem. 2000 43 4025
16. Gangjee A, Zeng Y, Talreja T, McGuire J J., Kisliuk R L., Queener S F., J. Med. Chem. 2007 50 3046
17. Jarkas N, McConathy J, Voll R J., Goodman M M., J. Med. Chem. 2005 48 4254
18. Liu L, Stelmach J E., Natarajan S R., Chen M.-H, Singh S B., Schwartz C D., Fitzgerald C E., OKeefe S J., Zaller D M., Schmatz D M., Doherty J B., Bioorg. Med. Chem. Lett. 2003 13 3979
19. Beard R L., Colon D F., Song T K., Davies P J. A., Kochhar D M., Chandraratna R A. S., J. Med. Chem. 1996 39 3556
20. Nagai Y, Irie A, Nakamura H, Hino K, Uno H, Nishimura H, J. Med. Chem. 1982 25 1065
21. Bonnet B, Soullez D, Girault S, Maes L, Landry V, Davioud-Charvet E, Sergheraert C, Bioorg. Med. Chem. 2000 8 95
22. Kondo T, Mitsudo T.-A, Chem. Rev. 2000 100 3205
23. Procter D J., J. Chem. Soc., Perkin Trans. 1 2001 335
24. Ley S V., Thomas A W., Angew. Chem. Int. Ed. 2003 43 5400
25. Itoh T, Mase T, Org. Lett. 2004 6 4587
26. Fernández-Rodríguez M A., Shen Q, Hartwig J F., J. Am. Chem. Soc. 2006 128 2180
27. Murata M, Buchwald S L., Tetrahedron 2004 60 7397
28. Mispelaere-Canivet C, Spindler J.-F, Perrio S, Beslin P, Tetrahedron 2005 61 5253
29. Zhang Y, Ngeow K C., Ying J Y., Org. Lett. 2007 9 3495
30. Jammi S, Barua P, Rout L, Saha P, Punniyamurthy T, Tetrahedron Lett. 2008 49 1484
31. Taniguchi N, J. Org. Chem. 2004 69 6904
32. Millois C, Diaz P, Org. Lett. 2000 2 1705
33. Wong Y.-C, Jayanth T T., Cheng C.-H, Org. Lett. 2006 8 5613
34. Correa A, Carril M, Bolm C, Angew. Chem. Int. Ed. 2008 47 2880
35. Sperotto E, vanKlink G P. M., deVries J G., vanKoten G, J. Org. Chem. 2008 73 5625
36. Kasibhatla S R., Hong K, Zhang L, Biamonte M A., Boehm M F., Shi J, Fan J, WO 03037860 2003, Bajji A C., Kim S.-H, Tangallapally R, Markovitz B, Trovatao R, Anderson M B., Wettstein D, Shenderovich M, WO 2009065035 2009, Chen J, Sperl G, Gullo V, Sista L, Hughes D, Peng Y, Pierceall W, Weiskopf A, Dushin R G., Kevin J I., WO 2008049105 2008, Taldone T, Chiosis G, Curr Top Med. Chem. 2009 9 1436
37. Chiosis G, Kang Y, Sun W, Expert Opin. Drug Discovery 2008 3 99
38. Workman P, Burrows F, Neckers L, Rosen N, Ann. N. Y. Acad. Sci. 2007 1113 202
39. Luo W, Rodina A, Chiosis G, BMC Neurosci. 2008 9 S7; Suppl. 2
40. Luo W, Sun W, Taldone T, Rodina A, Chiosis G, Mol. Neurodegener. 2010 5 24
41. Llauger L, He H, Kim J, Aguirre J, Rosen N, Peters U, Davies P, Chiosis G, J. Med. Chem. 2005 48 2892
42. Luo W, Dou F, Rodina A, Chip S, Kim J, Zhao Q, Moulick K, Aguirre J, Wu N, Greengard P, Chiosis G, Proc. Natl. Acad. Sci. U.S.A. 2007 104 9511
43. Cerchietti L C., Lopes E C., Yang S N., Hatzi K, Bunting K L., Tsikitas L A., Malik A, Robles A I., Walling J, Varticovski L, Shaknovich R, Bhalla K N., Chiosis G, Melnick A, Nat. Med. 2009 15 1369
44. Caldas-Lopes E, Cerchietti L, Ahn J H., Clement C C., Robles A I., Rodina A, Moulick K, Taldone T, Gozman A, Guo Y, Wu N, deStanchina E, White J, Gross S S., Ma Y, Varticovski L, Melnick A, Chiosis G, Proc. Natl. Acad. Sci. U.S.A. 2009 106 8368
45. Marubayashi S, Koppikar P, Taldone T, Abdel-Wahab O, West N, Bhagwat N, Caldas-Lopes E, Ross K N., Gonen M, Gozman A, Ahn J H., Rodina A, Ouerfeli O, Yang G, Hedvat C, Bradner J E., Chiosis G, Levine R L., J. Clin. Invest. 2010 120 3578
46. Tao H, Kang Y, Taldone T, Chiosis G, Bioorg. Med. Chem. Lett. 2009 19 415
47. Kwong F Y., Buchwald S L., Org. Lett. 2002 4 3517
48. She J, Jiang Z, Wang Y, Tetrahedron Lett. 2009 50 593
49. Buranaprasertsuk P, Chang J W. W., Chavasiri W, Chan P W. H., Tetrahedron Lett. 2008 49 2023
50. Bagley M C., Davis T, Dix M C., Fusillo V, Pigeaux M, Rokicki M J., Kipling D, J. Org. Chem. 2009 74 8336
51. Friden-Saxin M, Pemberton N, daSilvaAndersson K, Dyrager D, Friberg A, Grotli M, Luthman K, J. Org. Chem. 2009 74 2755
52. Al-Saleh B, El-Apasery M A., Hilmy N M., Elnagdi M H., J. Heterocycl. Chem. 2006 43 1575
53. Bargiggia F C., Murray W V., J. Org. Chem. 2005 70 9636
54. Xu Y, Guo Q.-X, Heterocycles 2004 63 903