Unsaturated Keto and Exomethylene Pyranonucleoside Analogues of Thymine and Uracil Exhibit Potent Antioxidant
Properties
126
Carbohydrate Research, Vol. 248, 1993, pp. 143-150.
doi:10.1016/0008-6215(93)84122-M
[8] M. Alaoui, M. J. Egron, M. Bessodes, K. Antonakis and I.
Chouroulinkov, “Relationship between the Structure and
Cytotoxic Activity of New Unsaturated Ketonucleosides
Tested on Eight Cell Lines,” European Journal of Me-
dicinal Chemistry, Vol. 22, No. 4, 1987, pp. 305-310.
doi:10.1016/0223-5234(87)90267-4
[9] F. Leclercq and K. Antonakis, “Unsaturated Ketonucleo-
tides: Synthesis of
and
Anomers of 1-(2,3-dide-
oxy-6-O-diethoxyphosphoryl-D-glycero-hex-2-enopyra-
nosyl-4-ulose) Thymine,” Carbohydrate Research, Vol.
263, No. 2, 1994, pp. 309-313.
doi:10.1016/0008-6215(94)00168-5
[10] G. S. Bisacchi, S. T. Chao, C. Bachard, J. P. Daris, S.
Innaimo, G. A. Jacobs, O. Kocy, P. Lapointe, A. Martel,
Z. Merchant, W. A. Slusarchyk, J. E. Sundeen, M. G.
Young, R. Colonno and R. Zahler, “BMS-200475, a
Novel Carbocyclic 2′-Deoxyguanosine Analog with Po-
tent and Selective Anti-Hepatitis B Virus Activity in Vi-
tro,” Bioorganic & Medicinal Chemistry Letters, Vol. 7,
No. 2, 1997, pp. 127-132.
doi:10.1016/S0960-894X(96)00594-X
[11] S. J. Yoo, H. O. Kim, Y. Lim, J. Kim and L. S. Jeong,
“Synthesis of Novel (2R,4R)- and (2S,4S)-Iso-Dideoxy-
nucleosides with Exocyclic Methylene as Potential Anti-
viral Agents,” Bioorganic & Medicinal Chemistry, Vol.
10, No. 1, 2002, pp. 215-226.
doi:10.1016/S0968-0896(01)00266-8
[12] P. Gunaga, M. Baba and L. S. Jeong, “Asymmetric Syn-
thesis of Novel Thioisodideoxynucleosides with Exocyc-
lic Methylene as Potential Antiviral Agents,” Journal of
Organic Chemistry, Vol. 69, No. 9, 2004, pp. 3208-3211.
[13] S. Manta, G. Agelis, T. Botić, A. Cencič and D. Komiotis,
“Fluoro-Ketopyranosyl Nucleosides: Synthesis and Bio-
logical Evaluation of 3-fluoro-2-keto-β-D-glucopyranosyl
Derivatives of N4-benzoyl Cytosine,” Bioorganic & Me-
dicinal Chemistry, Vol. 15, No. 2, 2007, pp. 980-987.
doi:10.1016/j.bmc.2006.10.033
[14] S. Manta, G. Agelis, T. Botić, A. Cencič and D. Komiotis,
“Unsaturated Fluoro-Ketopyranosyl Nucleosides: Syn-
thesis and Biological Evaluation of 3-fluoro-4-keto-β-D-
glucopyranosyl Derivatives of N4-benzoyl Cytosine and
N6-benzoyl Adenine,” European Journal of Medicinal
Chemistry, Vol. 43, No. 2, 2008, pp. 420-428.
doi:10.1016/j.ejmech.2007.04.001
[15] S. Manta, E. Tsoukala, N. Tzioumaki, A. Goropevšek, R.
T. Pamulapati, A. Cencič, J. Balzarini and D. Komiotis,
“Dideoxy Fluoro-Ketopyranosyl Nucleosides as Potent
Antiviral Agents: Synthesis and Biological Evaluation of
2,3- and 3,4-dideoxy-3-fluoro-4- and -2-keto-β-D-glu-
copyranosyl Derivatives of N4-benzoyl Cytosine,” Euro-
pean Journal of Medicinal Chemistry, Vol. 44, No. 6,
2009, pp. 2696-2704. doi:10.1016/j.ejmech.2009.01.020
[16] G. Agelis, N. Tzioumaki, T. Botić, A. Cencič and D.
Synthesis and Biological Evaluation of 1-(2,3,4-trideoxy-
2-methylene-β-D-glycero-hex-3-enopyranosyl)thymine,”
Bioorganic and Medicinal Chemistry, Vol. 15, No. 16,
2007, pp. 5448-5456.
Komiotis, “Exomethylene Pyranonucleosides: Efficient
doi:10.1016/j.bmc.2007.05.055
[17] G. Agelis, N. Tzioumaki, T. Tselios, T. Botić, A. Cencič
and D. Komiotis, “Synthesis and Molecular Modelling of
Unsaturated Exomethylene Pyranonucleoside Analogues
with Antitumor and Antiviral Activities,” European
Journal of Medicinal Chemistry, Vol. 43, No. 7, 2008, pp.
1366-1375. doi:10.1016/j.ejmech.2007.10.014
[18] N. Tzioumaki, E. Tsoukala, S. Manta, G. Agelis, J. Bal-
zarini and D. Komiotis, “Synthesis, Antiviral and Cy-
tostatic Evaluation of Unsaturated Exomethylene and
keto D-lyxopyranonucleoside Analogues,” Archiv der
Pharmazie, Vol. 342, No. 6, 2009, pp. 353-360.
doi:10.1002/ardp.200900004
[19] C. Spanou, S. Manta, D. Komiotis, A. Dervishi and D.
Kouretas, “Antioxidant Activity of a Series of Fluori-
nated Pyrano-nucleoside Analogues of N4-benzoyl Cyto-
sine and N6-benzoyl Adenine,” International Journal of
Molecular Sciences, Vol. 8, No. 7, 2007, pp. 695-704.
doi:10.3390/i8070695
[20] S. Manta, N. Tzioumaki, E. Tsoukala, A. Panagiotopou-
lou, M. Pelecanou, J. Balzarini and D. Komiotis, “Un-
saturated Dideoxy Fluoro-Ketopyranosyl Nucleosides as
New Cytostatic Agents: A Convenient Synthesis of 2,6-
dideoxy-3-fluoro-4-keto-β-D-glucopyranosyl Analogues
of Uracil, 5-Fluorouracil, Thymine, N4-benzoyl Cytosine
and N6-benzoyl Adenine,” European Journal of Medici-
nal Chemistry, Vol. 44, No. 11, 2009, pp. 4764-4771.
doi:10.1016/j.ejmech.2009.06.013
[21] S. Manta, E. Tsoukala, N. Tzioumaki, C. Kiritsis, J. Bal-
zarini and D. Komiotis, “Synthesis of 4,6-dideoxy-3-
fluoro-2-keto-β-D-glucopyranosyl Analogues of 5-Fluo-
rouracil, N6-Benzoyl Adenine, Uracil, Thymine, N4-Ben-
zoyl Cytosine and Evaluation of Their Antitumor Activi-
ties,” Bioorganic Chemistry, Vol. 38, No. 2, 2010, pp. 48-
55. doi:10.1016/j.bioorg.2009.11.001
[22] C. Mylonas and D. Kouretas, “Lipid Peroxidation and
Tissue Damage,” In Vivo, Vol. 13, No. 3, 1999, pp. 295-
310. doi:10.1016/j.ejmech.2011.01.005
[23] N. Tzioumaki, S. Manta, E. Tsoukala, J. V. Voorde, S.
Liekens, D. Komiotis and J. Balzarini, “Synthesis and
Biological Evaluation of Unsaturated Keto and Exome-
thylene D-Arabinopyranonucleoside Analogues: Novel
5-Fluorouracil Analogues That Target Thymidylate Syn-
thase,” European Journal of Medicinal Chemistry, Vol.
46, No. 4, 2011, pp. 993-1005. doi:10.1021/jf0100907
[24] S. T. Chang, J. H. Wu, S. Y. Wang, P. L. Kang, N. S.
Yang and L. F. Shyur, “Antioxidant Activity of Extracts
from Acacia Confusa Bark and Heartwood,” Journal of
Agricultural and Food Chemistry, Vol. 49, No. 7, 2001,
pp. 3420-3424.
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