Synthesis and characterization of 5-substituted 8-hydroxyquinoline derivatives and their metal complexes

Tetrahedron

Volumn 64, Issue 49, 2008, Pages 10986-10995

  Li, Lihua ^c   Xu, Bing ^a,b  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b BRANDEIS UNIVERSITY   (United States)

^c NONE

Author keywords

8 Hydroxyquinoline; Absorption; Emission; Metalloquinolate

Indexed keywords

5 AMINOMETHYL 8 HYDROXYQUINOLINE; METAL COMPLEX; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CHELATION; CHEMICAL STRUCTURE; DERIVATIZATION; FLAME PHOTOMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 54549101998     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.09.081     Document Type: Article

References (59)

1. Tang C.W., and Vanslyke S.A. Appl. Phys. Lett. 51 (1987) 913-915
2. Tang C.W., Vanslyke S.A., and Chen C.H. J. Appl. Phys. 65 (1989) 3610-3616
3. Chen C.H., and Shi J.M. Coord. Chem. Rev. 171 (1998) 161-174
4. Hopkins T.A., Meerholz K., Shaheen S., Anderson M.L., Schmidt A., Kippelen B., Padias A.B., Hall H.K., Peyghambarian N., and Armstrong N.R. Chem. Mater. 8 (1996) 344-351
5. Farruggia G., Iotti S., Prodi L., Montalti M., Zaccheroni N., Savage P.B., Trapani V., Sale P., and Wolf F.I. J. Am. Chem. Soc. 128 (2006) 344-350
6. Shirakawa M., Fujita N., Tani T., Kaneko K., and Shinkai S. Chem. Commun. (2005) 4149-4151
7. Wilcher F.J. Organic Analytical Reagents (1947), D. Van Nostrand, New York, NY
8. Kolthoff I.M., and Sandell E.B. Textbook of Quantitative Inorganic Analysis. 3rd ed. (1952), Macmillan, New York, NY
9. Shen A.Y., Chen C.P., and Roffler S. Life Sci. 64 (1999) 813-825
10. Collery P., Lechenault F., Cazabat A., Juvin E., Khassanova L., Evangelou A., and Keppler B. Anticancer Res. 20 (2000) 955-958
11. Zheng H.L., Weiner L.M., Bar-Am O., Epsztejn S., Cabantchik Z.I., Warshawsky A., Youdim N.B.H., and Fridkin M. Bioorg. Med. Chem. 13 (2005) 773-783
12. Estroff L.A., and Hamilton A.D. Chem. Rev. 104 (2004) 1201-1217
13. Jayawarna V., Smith A., Gough J.E., and Ulijn R.V. Biochem. Soc. Trans. 35 (2007) 535-537
14. Yang Z.M., Gu H.W., Zhang Y., Wang L., and Xu B. Chem. Commun. (2004) 208-209
15. Yang Z.M., Liang G.L., Ma M.L., Gao Y., and Xu B. J. Mater. Chem. 17 (2007) 850-854
16. Burckhalter J., and Leib R.I. J. Org. Chem. 26 (1961) 4078-4083
17. Manolova N., Ignatova M., and Rashkov I. Eur. Polym. J. 34 (1998) 1133-1141
18. Ignatova M., Manolova N., Rashkov I., Vassileva V., and Ignatov G. Plant Soil 227 (2000) 27-34
19. Williamson D.A., and Bowler B.E. Tetrahedron 52 (1996) 12357-12372
20. Lytle F.E., Storey D.R., and Juricich M.E. Spectrochim. Acta 29A (1973) 1357-1369
21. Moeller T. Ind. Eng. Chem., Anal. Ed. 15 (1943) 346-349
22. Goldman M., and Wehry E.L. Anal. Chem. 42 (1970) 1178-1185
23. Bardez E., Devol I., Larrey B., and Valeur B. J. Phys. Chem. B 101 (1997) 7786-7793
24. Prodi L., Bargossi C., Montalti M., Zaccheroni N., Su N., Bradshaw J.S., Izatt R.M., and Savage P.B. J. Am. Chem. Soc. 122 (2000) 6769-6770
25. Bhatnaga D., and Forster L.S. Spectrochim. Acta 21 (1965) 1803-1807
26. Moeller T., and Cohen A.J. J. Am. Chem. Soc. 72 (1950) 3546-3548
27. Zharovskii F.G., and Ryzhenko V.L. Seriya Fiziki ta Khimii 9 (1968) 62-66
28. Chen B.J., Sun X.W., and Li Y.K. Appl. Phys. Lett. 82 (2003) 3017-3019
29. Koenuma M., Kinashi H., Otake N., Sato S., and Saito Y. Acta Crystallogr. 32B (1976) 1267-1269
30. Summers A.O., Wireman J., Vimy M.J., Lorscheider F.L., Marshall B., Levy S.B., Bennett S., and Billard L. Antimicrob. Agents Chemother. 37 (1993) 825-834
31. Morones J.R., Elechiguerra J.L., Camacho A., Holt K., Kouri J.B., Ramirez J.T., and Yacaman M.J. Nanotechnology 16 (2005) 2346-2353
32. Cai Y.P., Zhang H.X., Xu A.W., Su C.Y., Chen C.L., Liu H.Q., Zhang L., and Kang B.S. J. Chem. Soc., Dalton Trans. (2001) 2429-2434
33. Shirakawa M., Fujita N., Tani T., Kaneko K., Ojima M., Fujii A., Ozaki M., and Shinkai S. Chem.-Eur. J. 13 (2007) 4155-4162
34. Zhang L.G., Ren X.G., Jiang D.P., Lu A.D., and Yuan J.S. Spectrosc. Lett. 29 (1996) 995-1001
35. Tao X.T., Suzuki H., Wada T., Sasabe H., and Miyata S. Appl. Phys. Lett. 75 (1999) 1655-1657
36. Tao X.T., Suzuki H., Wada T., Miyata S., and Sasabe H. J. Am. Chem. Soc. 121 (1999) 9447-9448
37. Zhang Y., Gu H.W., Yang Z.M., and Xu B. J. Am. Chem. Soc. 125 (2003) 13680-13681
38. Yang Z.M., Gu H.W., Fu D.G., Gao P., Lam J.K., and Xu B. Adv. Mater. 16 (2004) 1440-1444
39. Yang Z.M., and Xu B. Chem. Commun. (2004) 2424-2425
40. Yang Z.M., Xu K.M., Wang L., Gu H.W., Wei H., Zhang M.J., and Xu B. Chem. Commun. (2005) 4414-4416
41. Yang Z.M., and Xu B. Adv. Mater. 18 (2006) 3043-3046
42. Yang Z.M., Liang G.L., and Xu B. Chem. Commun. (2006) 738-740
43. Liang G.L., Xu K.M., Li L.H., Wang L., Kuang Y., Yang Z.M., and Xu B. Chem. Commun. (2007) 4096-4098
44. Yang Z.M., Liang G.L., Ma M.L., Abbah A.S., Lu W.W., and Xu B. Chem. Commun. (2007) 843-845
45. Yang Z.M., Liang G.L., Wang L., and Bing X. J. Am. Chem. Soc. 128 (2006) 3038-3043
46. Yang Z.M., Ho P.L., Liang G.L., Chow K.H., Wang Q.G., Cao Y., Guo Z.H., and Xu B. J. Am. Chem. Soc. 129 (2007) 266-267
47. Brinkmann M., Gadret G., Muccini M., Taliani C., Masciocchi N., and Sironi A. J. Am. Chem. Soc. 122 (2000) 5147-5157
48. Rajeswaran M., and Jarikov V.V. Acta Crystallogr. 59E (2003) M306-M307
49. Islam I., Ng K.Y., Chong K.T., Mcquade T.J., Hui J.O., Wilkinson K.F., Rush B.D., Ruwart M.J., Borchardt R.T., and Fisher J.F. J. Med. Chem. 37 (1994) 293-304
50. Seki M. Med. Res. Rev. 26 (2006) 434-482
51. Reddy J.A., and Low P.S. Crit. Rev. Ther. Drug Carr. Syst. 15 (1998) 587-627
52. Leamon C.P., and Low P.S. Drug Discovery Today 6 (2001) 44-51
53. Lu Y.J., Sega E., Leamon C.P., and Low P.S. Adv. Drug Delivery Rev. 56 (2004) 1161-1176
54. Fleisch H.A. Ann. Med. 29 (1997) 55-62
55. Rogers M.J., Watts D.J., and Russell R.G.G. Cancer 80 (1997) 1652-1660
56. Bankhead C. J. Natl. Cancer Inst. 89 (1997) 115-116
57. Stensbol T.B., Madsen U., and Krogsgaard-Larsen P. Curr. Pharm. Des. 8 (2002) 857-872
58. O'Shea R.D. Clin. Exp. Pharmacol. Physiol. 29 (2002) 1018-1023
59. Johansen T.N., Greenwood J.R., Frydenvang K., Madsen U., and Krogsgaard-Larsen P. Chirality 15 (2003) 167-179