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Synthesis, Electronic Absorption, Fluorescence and Live Time Spectroscopic Study of Some New 3,7-Disubstituted Coumarin Derivatives as New Fluorescent Probes
Asian Journal of Chemistry,
Vol. 28 No. 10 (2016): Vol 28 Issue 10
Abstract
The synthesis of several novel 3-heterocyclic substituent-7-methoxycoumarin derivatives were carried out starting from 3-acetyl-7-hydroxy-2H-chromen-2-one (3), which reacted with DMF-DMA affords enaminone 4 which transformed into pyranone 8, pyridine derivative 12a,b, 23, 24, triaroylbenzene 22 and fuaranone 17 with treatment with hippuric acid (5), acetyl acetone (12a), ethyl acetoacetate (12b), acetic acid and ammonium acetate, 3-acetyl-7- hydroxy-2H-chromen-2-one (3), acetic acid and 1,4-naphthoquinone (15) respectively. The UV-visible, fluorescence and live time spectra for compounds were determined. Most of them displayed high fluorescence quantum yields ranging from 0.70 to 0.99 and life times in the nanosecond range, which can make these new 3-heterocyclic substituent-7-methoxycoumarin compounds very useful as new fluorescent probes.
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- G. Jones, W.R. Jackson, C.Y. Choi and W.R. Bergmark, J. Phys. Chem., 89, 294 (1985); doi:10.1021/j100248a024.
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References
R.D.H. Murray, J. Medez and S.A. Brown, The Natural Coumarins: Occurrence, Chemistry and Biochemistry, Wiley, New York (1982).
R. Sabou, W.F. Hoelderich, D. Ramprasad and R. Weinand, J. Catal., 232, 34 (2005); doi:10.1016/j.jcat.2005.02.002.
A. Lacy and R.O. Kennedy, Curr. Pharm. Des., 10, 3797 (2004); doi:10.2174/1381612043382693.
Z.M. Nofal, M.I. El-Zahar and S.S. Abd El-Karim, Molecules, 5, 99 (2000); doi:10.3390/50200099.
M.A. Musa, V.L.D. Badisa, L.M. Latinwo, J. Cooperwood, A. Sinclair and A. Abdullah, Anticancer Res., 31, 2017 (2011).
Y. Takeuchi, L. Xie, L.M. Cosentino and K.H. Lee, Bioorg. Med. Chem. Lett., 7, 2573 (1997); doi:10.1016/S0960-894X(97)10050-6.
B. Musicki, A.M. Periers, P. Laurin, D. Ferroud, Y. Benedetti, S. Lachaud, F. Chatreaux, J.L. Haesslein, A. Lltis, C. Pierre, J. Khider, N. Tessot, M. Airault, J. Demassey, C. Dupuis-Hamelin, P. Lassaigne, A. Bonnefoy, P. Vicat and M. Klich, Bioorg. Med. Chem. Lett., 10, 1695 (2000); doi:10.1016/S0960-894X(00)00304-8.
O.A. Abd Allah, Farmaco, 55, 641 (2000); doi:10.1016/S0014-827X(00)00090-2.
E.A. Gunnewegh, A.J. Hoefnagel, R.S. Downing and H. van Bekkum, Recl. Trav. Chim. Pays Bas, 115, 226 (1996); doi:10.1002/recl.19961150407.
W.C. Sun, K.R. Gee and R.P. Haugland, Bioorg. Med. Chem. Lett., 8, 3107 (1998); doi:10.1016/S0960-894X(98)00578-2.
J. Oyamada, C. Jia, Y. Fujiwara and T. Kitamura, Chem. Lett., 380 (2002); doi:10.1246/cl.2002.380.
M.-T. Alonso, E. Brunet, O. Juanes and J.-C. Rodríguez-Ubis, J. Photochem. Photobiol. Chem., 147, 113 (2002); doi:10.1016/S1010-6030(01)00628-1.
M.H. Elnagdi, S.O. Abdallah, K.M. Ghoneim, E.M. Ebied and K.N. Kassab, J. Chem. Res., 44 (1997); doi:10.1039/a603731c.
K.H. Drexhage, in ed.: F.P. Schafer, Dye Lasers, Topics in Applied Physics, Springer, Berlin: vol. 1 (1973).
G. Jones, W.R. Jackson, C.Y. Choi and W.R. Bergmark, J. Phys. Chem., 89, 294 (1985); doi:10.1021/j100248a024.
L.M. Loew, S. Scully, L. Simpson and A.S. Waggoner, Nature, 281, 497 (1979); doi:10.1038/281497a0.
F.M. Altalbawy and E.A.M. Alsherbini, Chem. Sci. Transac., 4, 1018 (2015); doi:10.7598/cst2015.1101.
F.M.A. Altalbawy and E.A.M. Alsherbini, Asian J. Chem., 25, 6181 (2013); doi:10.14233/ajchem.2013.14305.
F.M.A. Altalbawy and E.S.S. Darwish, Asian J. Spectrosc., 16, 45 (2012).
A.S. Shawali, E.S.S. Darwish and F.M.A. Altalbawy, Asian J. Spectrosc., 11, 115 (2007).
A.S. Shawali, E.S.S. Darwish and F.M.A. Altalbawy, Asian J. Spectrosc., 12, 113 (2008).
.S. Darwish, M.A. Mosselhi, F.M. Altalbawy and H.A. Saad, Molecules, 16, 8788 (2011); doi:10.3390/molecules16108788.
A.S. Shawali, M.A. Mosselhi, F.M.A. Altablawy, T.A. Farghaly and N.M. Tawfik, Tetrahedron, 64, 5524 (2008); doi:10.1016/j.tet.2008.03.096.
A.S. Shawali, M.H. Abdelkader and F.M.A. Eltalbawy, Tetrahedron, 58, 2875 (2002); doi:10.1016/S0040-4020(02)00157-6.
A.S. Shawali, I.F. Zeid, M.H. Abdelkader, A.A. Elsherbini and F.M.A. Altalbawy, J. Chil. Chem. Soc., 48, 65 (2001); doi:10.1002/jccs.200100012.
H. Ammar, S. Fery-Forgues and R. El Gharbi, Dyes Pigments, 57, 259 (2003); doi:10.1016/S0143-7208(03)00028-7.
M.M. Hamad, A.F. El-Faragy, S.A. Said and A.A. Fahmy, Pak. J. Soc. Indic. Res., 33, 515 (1990).
S. Almazroa, M.H. Elnagdi and A.M.S. El-Din, J. Heterocycl. Chem., 41, 267 (2004); doi:10.1002/jhet.5570410219.
S.A. Tuccio, K.H. Drexhage and G.A. Reynolds, Opt. Coumun., 7, 248 (1973); doi:10.1016/0030-4018(73)90021-7.
K.H. Drexhage and G.A. Reynolds, VIII Inter. Quant. Electron. Conf., San Francisco, Calif, Paper F.1. (1974).
E.J. Schimitschek, J.A. Trias, P.R. Hammond and R.L. Atkins, Opt. Coumun., 11, 352 (1973); doi:10.1016/0030-4018(74)90234-X.
K.H. Drexhage, VII Intern. Quant. Electron. Conf., Montreal, Canada, Paper B. 5 (1972).
K.H. Drexhage, Laser Focus, 3, 35 (1973).
K.H. Drexhage, in ed.: F.P. Schafer, Structure and Properties of Laser Dyes, In: Dye Laser, Topics in Applied Physics, 1, 144 (1973).
G.A. Reynolds and K.H. Drexhage, Opt. Commun., 13, 222 (1975); doi:10.1016/0030-4018(75)90085-1.
J.B. Marling, J.G. Hawley, E.M. Liston and W.B. Grant, Appl. Opt., 13, 2317 (1974); doi:10.1364/AO.13.002317.
K. Das, B. Jain and H.S. Patel, J. Phys. Chem. A, 110, 1698 (2006); doi:10.1021/jp0556411.