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and 5% CO2 in a humidied incubator. MCF7 cells (5 ꢃ 103 per
well of 96 well plate) were seeded one day prior and then were
treated with these compounds (0–100 mM) for 48 hours. DMSO
(0.05% v/v) treated cells were considered as a control. At the end
of incubation, 850 mM of MTT was added to each well and
further incubated for 4 hours in the CO2 incubator. Then, the
MTT containing medium was replaced with 150 ml of MTT
solvent (4 mM HCl, 0.1% NP-40 in isopropanol) and further
incubated for 15 minutes at room temperature. Finally the
absorbance at 595 nm were measured in an Elisa plate reader
(Thermo Fisher Multiskan 80). The data were acquired from
three independent cell passages and the IC50 values were
calculated from the plot of cell viability vs. the concentration of
the complexes.
and J. Alfoldi, Tetrahedron Lett., 2002, 43, 5405; (c)
I. Burger, B. V. Burger, C. F. Albrecht, H. S. C. Spie and
P. Sandor, Phytochemistry, 1998, 49, 2087; (d)
R. J. Nachman, M. Honel, T. M. Williams, R. C. Halaska
and H. S. Mosher, J. Org. Chem., 1986, 51, 4802; (e)
M. Koos and H. S. Mosher, Carbohydr. Res., 1986, 146, 335;
(f) P. T. Ho, Can. J. Chem., 1979, 57, 381; (g) D. T. Williams
and J. K. N. Jones, Can. J. Chem., 1964, 42, 67; (h)
R. Schaffer, J. Am. Chem. Soc., 1959, 81, 5452.
7 (a) Y. Song, H. Ding, Y. Dou, R. Yang, Q. Sun, Q. Xiao and
Y. Ju, Synthesis, 2011, 9, 1442; (b) I. M. Lagoja, S. Pochet,
V. Boudou, R. Little, E. Lescrinier, J. Rozenski and
P. Herdewijn, J. Org. Chem., 2003, 68, 1867. Other
references there in.
8 (a) A. Panda, S. Das and S. Pal, Carbohydr. Res., 2014, 398, 13;
(b) H. R. Moon, H. O. Kim, K. M. Lee, M. W. Chun, J. H. Kim
and L. S. Jeong, Org. Lett., 2002, 4, 3501.
Acknowledgements
This work was supported by the Department of Science and
Technology (DST), India FAST track project grant no: SERB/F/
0287. The authors thank CIF, IIT Bhubaneswar for
characterization.
9 (a) D. Canals, D. Mormeneo, G. Fabrias, A. Llebaria, J. Casas
and A. Delgado, Bioorg. Med. Chem., 2009, 17, 235; (b)
R. J. B. H. N. van den Berg, T. J. Boltje, C. P. Verhagen,
R. E. J. N. Litjens, G. A. van der Marel and H. S. Overklee,
J. Org. Chem., 2006, 71, 836.
10 (a) R. Alibes, P. Bayon, P. March, M. Figueredo, J. Font and
G. Marjanet, Org. Lett., 2006, 8, 1617; (b) G. Mehta,
N. Mohal and S. Lakshminath, Tetrahedron Lett., 2000, 41,
3505.
Notes and references
1 (a) L. P. Jordheim, D. Durantel, F. Zoulim and C. Dumontet,
Nat. Rev. Drug Discovery, 2013, 12, 447; (b) G. Romeo,
U. Chiacchio, A. Corsaro and P. Merino, Chem. Rev., 2010, 11 (a) J. Liu, Y. Liu, X. Zhang, C. Zhang, Y. Gao, L. L. Wang and
110, 3337; (c) O. Arjona, A. M. Gomez, J. C. Lopez and
J. Plumet, Chem. Rev., 2007, 107, 1919; (d) C. M. Galmarini,
Y. Du, J. Org. Chem., 2012, 77, 9718; (b) P. Ghosal and
A. K. Shaw, J. Org. Chem., 2012, 77, 7627.
Electron. J. Oncol., 2002, 1, 22; (e) C. R. Wagner, V. V. Iyer 12 G. V. Ramana and B. V. Rao, Tetrahedron Lett., 2003, 44,
and E. J. McIntee, Med. Res. Rev., 2000, 20, 417; (f) X. Tan, 5103.
C. K. Chu and F. D. Boudinot, Adv. Drug Delivery Rev., 13 (a) L. S. Jeong, S. A. Choe, P. Gunaga, H. O. Kim, H. W. Lee,
1999, 39, 117; (g) G. J. Koomen, Recl. Trav. Chim. Pays-Bas,
1993, 112, 51; (h) C. Perigaud, G. Gosselin and
J. L. Imbach, Nucleosides Nucleotides, 1992, 11, 903; (i)
D. M. Huryn and M. Okabe, Chem. Rev., 1992, 92, 1745.
2 (a) O. Sari, V. Roy and L. A. Agrofoglio, in Chemical Synthesis
of Nucleoside Analogues, John Wiley & Sons, Inc., 2013, p. 49;
S. K. Lee, D. K. Tosh, A. Patel, K. K. Palaniappan, Z. G. Gao,
K. A. Jacobson and H. R. Moon, J. Med. Chem., 2007, 50, 3159;
(b) L. S. Jeong, H. W. Lee, K. A. Jacobson, H. O. Kim,
D. H. Shin, J. A. Lee, Z. G. Gao, C. Lu, H. T. Duong,
P. Gunaga, S. K. Lee, D. Z. Jin, M. W. Chun and
H. R. Moon, J. Med. Chem., 2006, 49, 273.
(b) Q. Wu and C. Simons, Synthesis, 2004, 10, 1533; (c) 14 (a) L. S. Jeong, S. Pal, S. A. Choe, W. J. Choi, K. A. Jacobson,
E. Ichikawa and K. Kato, Synthesis, 2002, 1, 1; (d)
E. Ichikawa and K. Kato, Curr. Med. Chem., 2001, 8, 385;
(e) M. Meldgaard and J. Wengel, J. Chem. Soc., Perkin
Trans. 1, 2000, 21, 3539; (f) E. S. H. El Ashry and
Z. G. Gao, A. M. Klutz, X. Hou, H. O. Kim, H. W. Lee,
D. K. Tosh and H. R. Moon, J. Med. Chem., 2008, 51, 6609;
(b) P. Gunaga, H. O. Kim, H. W. Lee, D. K. Tosh, J. S. Ryu,
S. Choi and L. S. Jeong, Org. Lett., 2006, 8, 4267.
N. Rashed, Curr. Org. Chem., 2000, 4, 609; (g) H. Gao and 15 (a) I. Carrera, M. C. Brovetto, J. C. Ramos and G. A. Seoane,
A. K. Mitra, Synthesis, 2000, 3, 329; (h) C. Meier, Synlett,
1998, 3, 233.
3 (a) T. B. Sells and V. Nair, Tetrahedron Lett., 1993, 34, 3527;
Tetrahedron Lett., 2009, 50, 5399; (b) A. D. Lebsack,
L. E. Overman and R. J. Valentekovich, J. Am. Chem. Soc.,
2001, 123, 4851.
(b) V. Nair and Z. Nuesca, J. Am. Chem. Soc., 1992, 114, 7951. 16 W. J. Choi, Y. J. Ko, G. Chandra, H. W. Lee, H. O. Kim,
4 Y. Terao, M. Akamatsu and K. Achiwa, Chem. Pharm. Bull.,
1991, 39, 823.
H. J. Koh, H. R. Moon, Y. H. Jung and L. S. Jeong,
Tetrahedron, 2012, 68, 1253.
5 J. A. Lee, H. R. Moon, H. O. Kim, K. R. Kim, K. M. Lee, 17 (a) W. J. Choi, H. J. Chung, G. Chandra, V. Alexander,
B. T. Kim, K. J. Hwang, M. W. Chun, K. A. Jacobson and
L. S. Jeong, J. Org. Chem., 2005, 70, 5006.
6 (a) K. S. Toti, M. Derudas, F. Pertusati, D. Sinnaeve,
F. V. Broeck, L. Margamuljana, J. C. Martins, P. Herdewijn,
J. Balzarini, C. McGuigan and S. V. Calenbergh, J. Org.
Chem., 2014, 79, 5097; (b) M. Koos, J. Micova, B. Steiner
L. X. Zhao, H. W. Lee, A. Nayak, M. S. Majik, H. O. Kim,
J. H. Kim, Y. B. Lee, C. H. Ahn, S. K. Lee and L. S. Jeong, J.
Med. Chem., 2012, 55, 4521; (b) L. S. Jeong, D. K. Tosh,
W. J. Choi, S. K. Lee, Y. J. Kang, S. Choi, J. H. Lee, H. Lee,
H. W. Lee and O. K. Hea, J. Med. Chem., 2009, 52, 5303; (c)
L. S. Jeong, L. X. Zhao, W. J. Choi, S. Pal, Y. H. Park,
82458 | RSC Adv., 2015, 5, 82450–82459
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