SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

Volumn 129, Issue 18, 2007, Pages 5962-5968

SNAr displacements with 6-(fluoro, chloro, bromo, iodo, and alkylsulfonyl)purine nucleosides: Synthesis, kinetics, and mechanism

(2) Liu, Jiangqiong a Robins, Morris J a

a Brigham Young University (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; CARBOXYLIC ACIDS; CHEMICAL SHIFT; NUCLEOPHILES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

DISPLACEMENT REACTIVITY; HALOPURINE COMPOUNDS; TRIFLUOROACETIC ACIDS;

NUCLEOTIDES;

PURINE NUCLEOSIDE DERIVATIVE; TRIFLUOROACETIC ACID;

ARTICLE; CHEMICAL REACTION; KINETICS; NITROGEN NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; PURINE SYNTHESIS; TITRIMETRY;

HALOGENS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PURINE NUCLEOSIDES;

EID: 34248550769 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja070021u Document Type: Article

Times cited : (71)

References (55)

1
- 34247633429
- Nucleic Acid Related Compounds. 144. For paper 143, see: Nowak, I.; Robins, M. J. J. Org. Chem., published online Mar 27, 2007 http://dx.doi.org/10.1021/jo062614d.
- Nucleic Acid Related Compounds. 144. For paper 143, see: Nowak, I.; Robins, M. J. J. Org. Chem., published online Mar 27, 2007 http://dx.doi.org/10.1021/jo062614d.

2
- 0032926819
- (a) Brathe, A.; Gundersen, L.-L.; Rise, F.; Eriken, A. B.; Vollsnes, A. V.; Wang, L. Tetrahedron 1999, 55, 211-228.
- (1999) Tetrahedron , vol.55 , pp. 211-228
- Brathe, A.¹ Gundersen, L.-L.² Rise, F.³ Eriken, A.B.⁴ Vollsnes, A.V.⁵ Wang, L.⁶

3
- 0000133784
- (b) Cocuzza, A. J.; Chidester, D. R.; Culp, S.; Fitzgerald, L.; Gilligan, P. Bioorg. Med. Chem. Lett. 1999, 9, 1063-1066.
- (1999) Bioorg. Med. Chem. Lett , vol.9 , pp. 1063-1066
- Cocuzza, A.J.¹ Chidester, D.R.² Culp, S.³ Fitzgerald, L.⁴ Gilligan, P.⁵

4
- 0035899193
- (c) Verdugo, D. E.; Cancilla, M. T.; Ge, X.; Gray, N. S.; Chang, Y.-T.; Schultz, P. G.; Negishi, M.; Leary, J. A.; Bertozzi, C. R. J. Med. Chem. 2001, 44, 2683-2686.
- (2001) J. Med. Chem , vol.44 , pp. 2683-2686
- Verdugo, D.E.¹ Cancilla, M.T.² Ge, X.³ Gray, N.S.⁴ Chang, Y.-T.⁵ Schultz, P.G.⁶ Negishi, M.⁷ Leary, J.A.⁸ Bertozzi, C.R.⁹

5
- 0036233469
- (d) Perez, O. D.; Chang, Y.-T.; Rosania, G.; Sutherlin, D.; Schultz, P. G. Chem. Biol. 2002, 9, 475-483.
- (2002) Chem. Biol , vol.9 , pp. 475-483
- Perez, O.D.¹ Chang, Y.-T.² Rosania, G.³ Sutherlin, D.⁴ Schultz, P.G.⁵

6
- 0025110788
- (a) Kappler, F.; Hampton, A. J. Med. Chem. 1990, 33, 2545-2551.
- (1990) J. Med. Chem , vol.33 , pp. 2545-2551
- Kappler, F.¹ Hampton, A.²

7
- 0035861620
- (b) Véliz, E. A.; Beal, P. A. J. Org. Chem. 2001, 66, 8592-8598.
- (2001) J. Org. Chem , vol.66 , pp. 8592-8598
- Véliz, E.A.¹ Beal, P.A.²

8
- 0346100650
- (c) Pathak, A. K.; Pathak, V.; Seitz, L. E.; Suling, W. J.; Reynolds, R. C. J. Med. Chem. 2004, 47, 273-276.
- (2004) J. Med. Chem , vol.47 , pp. 273-276
- Pathak, A.K.¹ Pathak, V.² Seitz, L.E.³ Suling, W.J.⁴ Reynolds, R.C.⁵

9
- 11144241597
- (d) Wanner, M. J.; Koch, M.; Koomen, G.-J. J. Med. Chem. 2004, 47, 6875-6883.
- (2004) J. Med. Chem , vol.47 , pp. 6875-6883
- Wanner, M.J.¹ Koch, M.² Koomen, G.-J.³

10
- 13444272999
- (e) Laufer, S. A.; Domeyer, D. M.; Scior, T. R. F.; Albrecht, W.; Hauser, D. R. J. J. Med. Chem. 2005, 48, 710-722.
- (2005) J. Med. Chem , vol.48 , pp. 710-722
- Laufer, S.A.¹ Domeyer, D.M.² Scior, T.R.F.³ Albrecht, W.⁴ Hauser, D.R.J.⁵

11
- 24344483502
- (f) Wang, J.-Q.; Kreklau, E. L.; Bailey, B. J.; Erickson, L. C.; Zheng, Q.-H. Bioorg. Med. Chem. 2005, 13, 5779-5786.
- (2005) Bioorg. Med. Chem , vol.13 , pp. 5779-5786
- Wang, J.-Q.¹ Kreklau, E.L.² Bailey, B.J.³ Erickson, L.C.⁴ Zheng, Q.-H.⁵

12
- 27144534479
- (g) Maruyama, T.; Moriwaka, N.; Demizu, Y.; Ohtsuka, M. Tetrahedron Lett. 2005, 46, 8225-8228.
- (2005) Tetrahedron Lett , vol.46 , pp. 8225-8228
- Maruyama, T.¹ Moriwaka, N.² Demizu, Y.³ Ohtsuka, M.⁴

13
- 33144458429
- (h) Nair, V.; Uchil, V.; Neamati, N. Bioorg. Med. Chem. Lett. 2006, 16, 1920-1923.
- (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 1920-1923
- Nair, V.¹ Uchil, V.² Neamati, N.³

14
- 0034069172
- (a) Hocek, M.; Holy, A.; Votruba, I.; Dvorakova, H. J. Med. Chem. 2000, 43, 1817-1825.
- (2000) J. Med. Chem , vol.43 , pp. 1817-1825
- Hocek, M.¹ Holy, A.² Votruba, I.³ Dvorakova, H.⁴

15
- 23044526799
- (b) Hoeck, M.; Holy, A.; Votruba, I.; Dvorakova, H. Collect. Czech. Chem. Commun. 2000, 65, 1683-1697.
- (2000) Collect. Czech. Chem. Commun , vol.65 , pp. 1683-1697
- Hoeck, M.¹ Holy, A.² Votruba, I.³ Dvorakova, H.⁴

16
- 0035537024
- (c) Hocek, M.; Holy, A.; Votruba, I.; Dvorakova, H. Collect. Czech. Chem. Commun. 2001, 66, 483-499.
- (2001) Collect. Czech. Chem. Commun , vol.66 , pp. 483-499
- Hocek, M.¹ Holy, A.² Votruba, I.³ Dvorakova, H.⁴

17
- 0242266522
- (d) Yao, S.-W.; Lopes, V. H. C.; Fernandez, F.; Garcia-Mera, X.; Morales, M.; Rodriguez-Borges, J. E.; Cordeiro, M. N. D. S. Bioorg. Med. Chem. 2003, 11, 4999-5006.
- (2003) Bioorg. Med. Chem , vol.11 , pp. 4999-5006
- Yao, S.-W.¹ Lopes, V.H.C.² Fernandez, F.³ Garcia-Mera, X.⁴ Morales, M.⁵ Rodriguez-Borges, J.E.⁶ Cordeiro, M.N.D.S.⁷

18
- 4444340442
- (e) Fernandez, F.; Garcia-Mera, X.; Morales, M.; Vilarino, L.; Caamano, O.; De Clercq, E. Tetrahedron 2004, 60, 9245-9253.
- (2004) Tetrahedron , vol.60 , pp. 9245-9253
- Fernandez, F.¹ Garcia-Mera, X.² Morales, M.³ Vilarino, L.⁴ Caamano, O.⁵ De Clercq, E.⁶

19
- 10644259620
- (f) Hocek, M.; Pohl, R. Synthesis 2004, 2869-2876.
- (2004) Synthesis , pp. 2869-2876
- Hocek, M.¹ Pohl, R.²

20
- 0026514219
- (a) Matsuda, A.; Shinozaki, M.; Yamaguchi, T.; Homma, H.; Nomoto, R.; Miyasaka, T.; Watanabe, Y.; Abiru, T. J. Med. Chem. 1992, 35, 241-252.
- (1992) J. Med. Chem , vol.35 , pp. 241-252
- Matsuda, A.¹ Shinozaki, M.² Yamaguchi, T.³ Homma, H.⁴ Nomoto, R.⁵ Miyasaka, T.⁶ Watanabe, Y.⁷ Abiru, T.⁸

21
- 0036189146
- (b) Brathe, A.; Andresen, G.; Gundersen, L.-L.; Malterud, K. E.; Rise, F. Bioorg. Med. Chem. 2002, 10, 1581-1586.
- (2002) Bioorg. Med. Chem , vol.10 , pp. 1581-1586
- Brathe, A.¹ Andresen, G.² Gundersen, L.-L.³ Malterud, K.E.⁴ Rise, F.⁵

22
- 0037430585
- (c) Brathe, A.; Gundersen, L.-L.; Nissen-Meyer, J.; Rise, F.; Spilsberg, B. Bioorg. Med. Chem. Lett. 2003, 13, 877-880.
- (2003) Bioorg. Med. Chem. Lett , vol.13 , pp. 877-880
- Brathe, A.¹ Gundersen, L.-L.² Nissen-Meyer, J.³ Rise, F.⁴ Spilsberg, B.⁵

23
- 10344240898
- (d) Naus, P.; Votruba, I.; Hocek, M. Collect. Czech. Chem. Commun. 2004, 69, 1955-1970.
- (2004) Collect. Czech. Chem. Commun , vol.69 , pp. 1955-1970
- Naus, P.¹ Votruba, I.² Hocek, M.³

24
- 19344365981
- (e) Turek, P.; Kotora, M.; Hocek, M.; Votruba, I. Collect. Czech. Chem. Commun. 2005, 70, 339-349.
- (2005) Collect. Czech. Chem. Commun , vol.70 , pp. 339-349
- Turek, P.¹ Kotora, M.² Hocek, M.³ Votruba, I.⁴

25
- 28444499086
- (f) Berg, T. C.; Gundersen, L.-L.; Eriksen, A. B.; Malterud, K. E. Eur. J. Org. Chem. 2005, 4988-4994.
- (2005) Eur. J. Org. Chem , pp. 4988-4994
- Berg, T.C.¹ Gundersen, L.-L.² Eriksen, A.B.³ Malterud, K.E.⁴

26
- 33947449188
- Bunnet, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273-412.
- (1951) Chem. Rev , vol.49 , pp. 273-412
- Bunnet, J.F.¹ Zahler, R.E.²

27
- 4444383383
- Liu, J.; Janeba, Z.; Robins, M. J. Org. Lett. 2004, 6, 2917-2919.
- (2004) Org. Lett , vol.6 , pp. 2917-2919
- Liu, J.¹ Janeba, Z.² Robins, M.J.³

28
- 0034597503
- and references cited therein
- Lin, X.; Robins, M. J. Org. Lett. 2000, 2, 3497-3499 and references cited therein.
- (2000) Org. Lett , vol.2 , pp. 3497-3499
- Lin, X.¹ Robins, M.J.²

29
- 0000310421
- Robins, M. J.; Barr, P. J.; Giziewicz, J. Can. J. Chem. 1982, 60, 554-557.
- (1982) Can. J. Chem , vol.60 , pp. 554-557
- Robins, M.J.¹ Barr, P.J.² Giziewicz, J.³

30
- 0343332932
- Parish, R. C.; Stock, L. M. J. Org. Chem. 1965, 30, 927-929.
- (1965) J. Org. Chem , vol.30 , pp. 927-929
- Parish, R.C.¹ Stock, L.M.²

31
- 33847088576
- Gassman, P. G.; Schenk, W. N. J. Org. Chem. 1977, 42, 918-920.
- (1977) J. Org. Chem , vol.42 , pp. 918-920
- Gassman, P.G.¹ Schenk, W.N.²

32
- 0019781093
- (a) Robins, M. J.; Uznański, B. Can. J. Chem. 1981, 59, 2608-2611.
- (1981) Can. J. Chem , vol.59 , pp. 2608-2611
- Robins, M.J.¹ Uznański, B.²

33
- 0022492192
- (b) Secrist, J. A., III; Bennett, L. L., Jr.; Allan, P. W.; Rose, L. M.; Chang, C.-H.; Montgomery, J. A. J. Med. Chem. 1986, 29, 2069-2074.
- (1986) J. Med. Chem , vol.29 , pp. 2069-2074
- Secrist III, J.A.¹ Bennett Jr., L.L.² Allan, P.W.³ Rose, L.M.⁴ Chang, C.-H.⁵ Montgomery, J.A.⁶

34
- 18244380805
- Liu, J.; Robins, M. J. Org. Lett. 2005, 7, 1149-1151.
- (2005) Org. Lett , vol.7 , pp. 1149-1151
- Liu, J.¹ Robins, M.J.²

35
- 33947484336
- (a) Gerster, J. F.; Jones, J. W.; Robins, R. K. J. Org. Chem. 1963, 28, 945-948.
- (1963) J. Org. Chem , vol.28 , pp. 945-948
- Gerster, J.F.¹ Jones, J.W.² Robins, R.K.³

36
- 0019864944
- (b) Robins, M. J.; Uznański, B. Can. J. Chem. 1981, 59, 2601-2607.
- (1981) Can. J. Chem , vol.59 , pp. 2601-2607
- Robins, M.J.¹ Uznański, B.²

37
- 0018382228
- (a) Nair, V.; Richardson, S. G. Tetrahedron Lett. 1979, 1181-1184.
- (1979) Tetrahedron Lett , pp. 1181-1184
- Nair, V.¹ Richardson, S.G.²

38
- 0019196854
- (b) Nair, V.; Richardson, S. G. J. Org. Chem. 1980, 45, 3969-3974.
- (1980) J. Org. Chem , vol.45 , pp. 3969-3974
- Nair, V.¹ Richardson, S.G.²

39
- 0037144688
- (a) Francom, P.; Janeba, Z.; Shibuya, S.; Robins, M. J. J. Org. Chem. 2002, 67, 6788-6796.
- (2002) J. Org. Chem , vol.67 , pp. 6788-6796
- Francom, P.¹ Janeba, Z.² Shibuya, S.³ Robins, M.J.⁴

40
- 0037462415
- (b) Francom, P.; Robins, M. J. J. Org. Chem. 2003, 68, 666-669.
- (2003) J. Org. Chem , vol.68 , pp. 666-669
- Francom, P.¹ Robins, M.J.²

41
- 0036914685
- Schlosser, M.; Cottet, F. Eur. J. Org. Chem. 2002, 4181-4184.
- (2002) Eur. J. Org. Chem , pp. 4181-4184
- Schlosser, M.¹ Cottet, F.²

42
- 0033618139
- (a) Lakshman, M. K.; Keeler, J. C.; Hilmer, J. H.; Martin, J. Q. J. Am. Chem. Soc. 1999, 121, 6090-6091.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 6090-6091
- Lakshman, M.K.¹ Keeler, J.C.² Hilmer, J.H.³ Martin, J.Q.⁴

43
- 0034802548
- (b) Lakshman, M. K.; Hilmer, J. H.; Martin, J. Q.; Keeler, J. C.; Dinh, Y. Q. V.; Ngassa, F. N.; Russon, L. M. J. Am. Chem. Soc. 2001, 123, 7779-7787.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 7779-7787
- Lakshman, M.K.¹ Hilmer, J.H.² Martin, J.Q.³ Keeler, J.C.⁴ Dinh, Y.Q.V.⁵ Ngassa, F.N.⁶ Russon, L.M.⁷

44
- 0038576280
- (c) Lakshman, M. K.; Gunda, P. Org. Lett. 2003, 5, 39-42.
- (2003) Org. Lett , vol.5 , pp. 39-42
- Lakshman, M.K.¹ Gunda, P.²

45
- 0037696809
- (d) Lakshman, M. K.; Ngassa, F. N.; Bae, S.; Buchanan, D. G.; Hahn, H.-T.; Mah, H. J. Org. Chem. 2003, 68, 6020-6030.
- (2003) J. Org. Chem , vol.68 , pp. 6020-6030
- Lakshman, M.K.¹ Ngassa, F.N.² Bae, S.³ Buchanan, D.G.⁴ Hahn, H.-T.⁵ Mah, H.⁶

46
- 0017764994
- (a) Markowski, V.; Sullivan, G. R.; Roberts, J. D. J. Am. Chem. Soc. 1977, 99, 714-718.
- (1977) J. Am. Chem. Soc , vol.99 , pp. 714-718
- Markowski, V.¹ Sullivan, G.R.² Roberts, J.D.³

47
- 0001749729
- (b) Gonnella, N. C.; Nakanishi, H.; Holtwick, J. B.; Horowitz, D. S.; Kanamori, K.; Leonard, N. J.; Roberts, J. D. J. Am. Chem. Soc. 1983, 105, 2050-2055.
- (1983) J. Am. Chem. Soc , vol.105 , pp. 2050-2055
- Gonnella, N.C.¹ Nakanishi, H.² Holtwick, J.B.³ Horowitz, D.S.⁴ Kanamori, K.⁵ Leonard, N.J.⁶ Roberts, J.D.⁷

48
- 0344530801
- Whitfield, H. J.; Griffin, R. J.; Hardcastle, I. R.; Henderson, A.; Meneyrol, J.; Mesguiche, V.; Sayle, K. L.; Golding, B. T. Chem. Commun. 2003, 2802-2803.
- (2003) Chem. Commun , pp. 2802-2803
- Whitfield, H.J.¹ Griffin, R.J.² Hardcastle, I.R.³ Henderson, A.⁴ Meneyrol, J.⁵ Mesguiche, V.⁶ Sayle, K.L.⁷ Golding, B.T.⁸

49
- 3242762940
- Wang, G.; Gaffney, B. L.; Jones, R. A. J. Am. Chem. Soc. 2004, 126, 8908-8909.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 8908-8909
- Wang, G.¹ Gaffney, B.L.² Jones, R.A.³

50
- 5844297911
- (a) Forlani, L.; Tortelli, V. J. Chem. Res., Synop. 1982, 62-63.
- (1982) J. Chem. Res., Synop , pp. 62-63
- Forlani, L.¹ Tortelli, V.²

51
- 0348001126
- (b) Forlani, L. J. Chem. Res., Synop. 1984, 260-261.
- (1984) J. Chem. Res., Synop , pp. 260-261
- Forlani, L.¹

52
- 0016845044
- Wetzel, R.; Eckstein, F. J. Org. Chem. 1975, 40, 658-660.
- (1975) J. Org. Chem , vol.40 , pp. 658-660
- Wetzel, R.¹ Eckstein, F.²

53
- 34248533217
- Experimental details are in the Supporting Information
- Experimental details are in the Supporting Information.

54
- 84986760697
- Sibi, M. P.; Lichter, R. L. Org. Magn. Reson. 1980, 14, 494-496.
- (1980) Org. Magn. Reson , vol.14 , pp. 494-496
- Sibi, M.P.¹ Lichter, R.L.²

55
- 3543005929
- Terrazas, M.; Ariza, X.; Farrax, J.; Guisado-Yang, J. M.; Vilarrasa, J. J. Org. Chem. 2004, 69, 5473-5475.
- (2004) J. Org. Chem , vol.69 , pp. 5473-5475
- Terrazas, M.¹ Ariza, X.² Farrax, J.³ Guisado-Yang, J.M.⁴ Vilarrasa, J.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.