Synthesis of novel fluorinated coumarins: Excellent UV-light excitable fluorescent dyes

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 22, 1998, Pages 3107-3110

  Sun, Wei Chuan ^a,b   Gee, Kyle R ^a   Haugland, Richard P ^a  

^a MOLECULAR PROBES INC   (United States)

^b EPIX Pharmaceuticals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DIFLUORORESORCINOL; 3 CARBOXY 6,8 DIFLUORO 7 HYDROXYCOUMARIN; 6,8 DIFLUORO 7 HYDROXY 4 METHYLCOUMARIN; COUMARIN DERIVATIVE; FLUORESCENT DYE; FLUORINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BLEACHING; DRUG STABILITY; DRUG SYNTHESIS; FLUORESCENCE;

EID: 0032541999     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00578-2     Document Type: Article

References (21)

1. 2. Song, L.; Varma, C.A.G.O.; Verhoeven, J.W.; Tanke, H. Biophys. J. 1996, 70, 2959. and references cited therein.
2. 3 Adamczyk, M.; Cornwell, M; Huff, J.; Rege, S.; Rao, T.V.S. Bioorg. Med. Chem. Lett. 1997, 7, 1985.
3. 4. (a) Feraley, H.N.; Walker, P.O. Biochem. J. 1965, 97, 95.
4. (b) Robinson, D.; Willcox, P. Biochim. Biophys. Acta 1969, 191, 183.
5. 5. Steven, F.S.; Al-Ahmad; R.K. FEBS Lett. 1983, 335.
6. 6. Krishnaswamy, S.; Vlasuk, G.P.; Bergum, P.W. Biochemistry 1994, 33, 7897.
7. 7. (a) Maiden, M.F.J.; Tanner, A.; Macuch, P.J. J. Clin. Microbiol. 1996, 34, 376.
8. (b) Yano, S.-I; Kawata, Y.; Delbarre, S.; Kojima, H. Biosci. Biotech. Biochem. 1992, 56, 1310.
9. 8. (a) Villari, P.; Iannuzzo, M.; Torre, I. Lett. Appl. Microbiol. 1997, 24, 286.
10. 9. Moriya, T. Bull. Chem. Soc. Jpn. 1983, 56, 6.
11. 10 (a) Heaney, H.; Proce, A.P. Chem. Commun. 1971, 894.
12. (b) Abdel-Megeid, F.M.E.; El-Kaschef, M.A.F.; Ghattas, A.A.G. Egypt. J. Chem. 1977, 5, 453.
13. (c) Fomenko, T.V.; Danilenko, N.I.; Gerasimova, T.N.; Fokin, E.P. Izv. Sib. Otd. Akad Nauk. SSSR. Ser. Khim. Nauk. 1981, 2, 127.
14. (d) Bertram, H.-J.; Böhm, S.; Born, L. Synthesis 1991, 937.
15. 11. von Pechmann, H.; Duisberg, C. Ber. 1883,16, 2119.
16. 12. Sun, W.-C.; Gee, K.R.; Klaubert, D.H.; Haugland, R.P. J. Org. Chem. 1997, 62, 6469.
17. 13. The following β-ketoesters were used: ethyl acetoacetate, ethyl 4,4,4-trifluoroacetoacetate, ethyl pentafluorobenzoylacetate, diethyl acetylsuccinate.
18. 19F, respectively. 3: δ 10.96 (s, 1H), 7.41 (dd, J = 7.4, 1.8, 1H), 6.95 (t, J = 8.6, 1H), 6.22 (s, 1H), 2.37 (s, 3H). φ 155.04 (d, J = 7.1). 4: δ 7.57 (d, J = 11.6, 1H), 6.89 (d, J = 7.2, 1H), 6.20 (s, 1H), 2.35 (s, 3H). φ 135.06 (dd, J = 11.3, 7.1). 5: δ 10.95 (s, 1H), 6.58 (d, J = 13.4, 1H), 6.11 (s, 1H), 2.43 (d, J = 6.0, 3H). φ 108.84 (m). 6: δ 7.48 (d, J = 9.9, 1H), 6.31 (s, 1H), 2.36 (d, J = 1.0, 3H). φ 131.66 (t, J = 10.4, 1F), 149.31 (d, J = 9.0, 1F). 7: δ 6.18 (s, 1H), 2.44 (d, J = 6.0, 3H). φ 140.04 (m, 1F), 155.24 (s, 1F), 158.74 (m, 1F). 8: δ 7.48 (d, J = 12.1, 1H), 3.56 (s, 2H), 2.32 (s, 3H). φ 128.03 (dd, J = 12.3,10.0, 1F), 147.46 (br, 1F). 10: δ 7.42 (d, J = 11.3, 1H), 7.02 (d, J = 7.4, 1H), 6.86 (s, 1H). φ 59.45 (s, 3F), 133.15 (dd, J = 11.2, 7.3, 1F). 11: δ 7.33 (d, J = 11.1, 1H), 6.99 (s, 1H). φ 59.38 (s, 3F), 129.93 (t, J = 9.9, 1F), 147.78 (d, J = 9.3, 1F). 12: δ 8.53 (d, J = 1.2, 1H), 7.45 (d, J = 10.5, 1H). φ 131.67 (t, J = 12.0, 1F), 153.45 (br, 1F). 13 δ 8.53 (d, J = 1.2, 1H), 7.45 (d, J = 10.5, 1H), 4.23 (q, J = 7.1, 2H), 1.28 (t, J = 7.2, 3H). φ 131.67 (t, J = 11.9, 1F), 153.46 (br, 1F).
19. 15 von Pechmann, H.; Graezer, E. Chem. Ber. 1901, 34, 378.
20. 16. Weidner-Wells, M.A; Fraga-Spano, S.A. Syn. Commun. 1996, 26, 2775.
21. 3: C, 48.29; H, 2.32. Found: C, 47.87; H, 2.62.