4-N-Methyl-N′-(2-dihydroxyboryl-benzyl)amino benzonitrile and its boronate analogue sensing saccharides and fluoride ion

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 9, 2007, Pages 2629-2633

  Tan, Wei ^a,b   Zhang, Deqing ^a   Zhu, Daoben ^a  

^a PEKING UNIVERSITY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

4 N,N dimethylaminobenzonitrile; Boronic acid; Fluorescence; Fluoride ion; Saccharides sensor

Indexed keywords

AMINE; BENZONITRILE; BENZYL DERIVATIVE; BORONIC ACID DERIVATIVE; CARBOHYDRATE; FLUORIDE; FRUCTOSE; GALACTOSE; GLUCOSE; MANNOSE; METHYL GROUP;

ARTICLE; FLUORESCENCE SPECTROSCOPY; MOLECULAR INTERACTION; QUANTUM YIELD; SENSOR; SPECTRAL SENSITIVITY;

BORONIC ACIDS; CARBOHYDRATES; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; FLUORESCENT DYES; FLUORIDES; FRUCTOSE; IONS; KINETICS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR PROBES; NITRILES; SPECTROMETRY, FLUORESCENCE;

EID: 33947727501     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.01.099     Document Type: Article

References (55)

1. See for examples. Yoon J., and Czarnik A.W. J. Am. Chem. Soc. 114 (1992) 5874
2. James T.D., Samankumara Sandanayake K.R.A., and Shinkai S. Angew. Chem., Int. Ed. 35 (1996) 1910
3. Samankumara Sandanayake K.R.A., James T.D., and Shinkai S. Pure Appl. Chem. 68 (1996) 1207
4. Davis A.P., and Wareham R.S. Angew. Chem., Int. Ed. 38 (1999) 2978
5. Cao H., and Heagy M.D. J. Fluoresc. 14 (2004) 569
6. James T.D., Linnane P., and Shinkai S. Chem. Commun. (1996) 281
7. Yan J., Fang H., and Wang B. Med. Res. Rev. 25 (2005) 490 and further references therein
8. See for examples. Nakata E., Nagase T., Shinkai S., and Hamachi I. J. Am. Chem. Soc. 126 (2004) 490
9. Sugasaki A., Sugiyasu K., Takeuchi M., and Shinkai S. J. Am. Chem. Soc. 123 (2001) 10239
10. James T.D., Samankumara Sandanayake K.R.A., and Shinkai S. Nature 374 (1995) 345
11. James T.D., Shinmori H., and Shinkai S. Chem. Commun. (1997) 71
12. Tsukagoshi K., and Shinkai S. J. Org. Chem. 56 (1991) 4089
13. James T.D., Samankumara Sandanayake K.R.A., and Shinkai S. J. Chem. Soc. Chem. Commun. (1994) 477
14. See for examples. Cooper C.R., and James T.D. Chem. Lett. (1998) 883
15. Ward C.J., Patel P., and James T.D. Org. Lett. 4 (2002) 477
16. Cooper C.R., and James T.D. J. Chem. Soc., Perkin Trans. 1 (2000) 963
17. Arimori S., Bell M.L., Oh C.S., and James T.D. Org. Lett. 4 (2002) 4249
18. Kijima H., Takeuchi M., Robertson A., Shinkai S., Cooper C., and James T.D. Chem. Commun. (1999) 2011
19. Arimori S., Ushiroda S., Peter L.M., Jenkins A.T.A., and James T.D. Chem. Commun. (2002) 2368
20. Arimori S., Bosch L.I., Ward C.J., and James T.D. Tetrahedron Lett. 42 (2001) 4553
21. Bosch L.I., Mahon M.F., and James T.D. Tetrahedron Lett. 45 (2004) 2859
22. Gao X., Zhang Y., and Wang B. Org. Lett. 5 (2003) 4615
23. Gao X., Zhang Y., and Wang B. New J. Chem. 29 (2005) 579
24. Wang J., Jin S., and Wang B. Tetrahedron Lett. 46 (2005) 7003
25. Gao X., Zhang Y., and Wang B. Tetrahedron 61 (2005) 9111
26. Yang W., Yan J., Springsteen G., Deeter S., and Wang B. Bioorg. Med. Chem. Lett. 13 (2003) 1019
27. Zhang Y., Gao X., Hardcastle K., and Wang B. Chem. Eur. J. 12 (2006) 1377
28. Wang Z., Zhang D., and Zhu D. J. Org. Chem. 70 (2005) 5729
29. Tan W., Wang Z., Zhang D., and Zhu D. Sensors 6 (2006) 954
30. Yu Y., Zhang D., Tan W., Wang Z., and Zhu D. Bioorg. Med. Chem. Lett. (2006) 10.1016/j.bmcl.2006.09.081
31. Davis A.P., and Wareham R.S. Angew. Chem., Int. Ed. 38 (1999) 2978 and further references therein
32. Fang J., Selvi S., Liao J., Slanina Z., Chen C., and Chou P. J. Am. Chem. Soc. 126 (2004) 3559
33. Lippert E., Lüder W., Moll F., Nagele H., Boos H., Prigge H., and Siebold-Blankenstein I. Angew. Chem. 73 (1961) 695
34. Rettig W. Angew. Chem., Int. Ed. Engl. 25 (1986) 971
35. Grabowski Z.R., Rotkiewicz K., and Rettig W. Chem. Rev. 103 (2003) 3899 and references therein
36. Collins G.E., Choi L.S., and Callahan J.H. J. Am. Chem. Soc. 120 (1998) 1474
37. Létard J.F., Delmond S., Lapouyade R., Braun D., Rettig W., and Kreissler M. Recl. Trav. Chim. Pays-Bas 114 (1995) 517
38. Wu F.Y., and Jiang Y.B. Chem. Phys. Lett. 355 (2002) 438
39. Wu F.Y., Ma L.H., and Jiang Y.B. Anal. Sci. 17 Suppl. (2001) i801
40. Wu F.Y., Li Z., Wen Z.C., Zhou N., Zhao Y.F., and Jiang Y.B. Org. Lett. 4 (2002) 3203
41. Wen Z.C., and Jiang Y.B. Tetrahedron 60 (2004) 11109
42. Hartley J.H., James T.D., and Ward C.J. J. Chem. Soc., Perkin Trans. 1 (2000) 3155
43. Wiskur S.L., Lavigne J.J., Ait-Haddou H., Lynch V., Chiu Y.H., Canary J.W., and Anslyn E.V. Org. Lett. 3 (2001) 1311
44. See Ref. 1a.
45. Yamaguchi S., Akiyama S., and Tamao K. J. Am. Chem. Soc. 122 (2000) 6335
46. Yamaguchi S., Akiyama S., and Tamao K. J. Am. Chem. Soc. 123 (2001) 11372
47. Yamaguchi S., Shirasaka T., Akiyama S., and Tamao K. J. Am. Chem. Soc. 124 (2002) 8816
48. Kubo Y., Yamamoto M., Ikeda M., Takeuchi M., Shinkai S., Yamaguchi S., and Tamao K. Angew. Chem., Int. Ed. 42 (2003) 2036
49. Liu X.Y., Bai D.R., and Wang S. Angew. Chem., Int. Ed. 45 (2006) 5475
50. Liu Z., Shi M., Li F., Fang Q., Chen Z., Yi T., and Huang C. Org. Lett. 7 (2005) 5481
51. Kubo Y., Kobayashi A., Ishida T., Misawa Y., and James T.D. Chem. Commun. (2005) 2846
52. Cooper C.R., Spencer N., and James T.D. Chem. Commun. (1998) 1365
53. 2: 334.1853 [M]; found: 334.1848.
54. Rettig W. J. Lumin. 26 (1980) 21
55. Rettig W. J. Phys. Chem. 86 (1982) 1970