Paper
RSC Advances
silica gel column chromatography with CH
2
Cl
2
as an eluent in
6 A. M. Katsori and D. Hadjipavlou-Litina, Expert Opin. Ther.
Pat., 2011, 21, 1575–1596.
1
35% yield (0.84 g, 3.5 mmol). H NMR (500 MHz, CD CN, 293 K)
3
d (ppm): 12.91 (s, 1H), 8.17 (d, J ¼ 15.5 Hz, 1H), 8.09 (dd, J ¼ 8.6,
7 P. Singh, A. Anand and V. Kumar, Eur. J. Med. Chem., 2014,
85, 758–777.
8 G. Romanelli, G. Pasquale, A. Sathicq, H. Thomas, J. Autino
and P. Vazquez, J. Mol. Catal. Chem., 2011, 340, 24–32.
9 M. J. Climent, A. Corma, S. Iborra and A. Velty, J. Catal., 2004,
221, 474–482.
1
1
1
6
.6 Hz, 1H), 7.92 (d, J ¼ 15.5 Hz, 1H), 7.75 (dd, J ¼ 7.5, 1.6 Hz,
H), 7.69 (s, 1H), 7.55 (td, J ¼ 7.9, 1.6 Hz, 1H), 7.32 (td, J ¼ 7.7,
.6 Hz, 1H), 6.99 (td, J ¼ 7.6, 1.5 Hz, 1H), 6.98 (t, J ¼ 7.3 Hz, 1H),
1
3
.97 (d, J ¼ 7.3 Hz, 1H), 6.96 (d, J ¼ 8.0 Hz, 1H); C NMR (125
3
MHz, CD CN, 293 K) d (ppm): 194.59, 163.37, 156.80, 140.53,
1
1
36.44, 132.39, 130.36, 129.53, 121.66, 120.45, 120.42, 120.04, 10 J. Y. Park, J. A. Ko, D. W. Kim, Y. M. Kim, H. J. Kwon,
ꢀ
18.99, 117.99, 116.26. HRMS (Orbitrap) m/z: [M ꢀ H] calcu-
H. J. Jeong, C. Y. Kim, K. H. Park, W. S. Lee and Y. B. Ryu,
J. Enzym. Inhib. Med. Chem., 2016, 31, 23–30.
lated for C H O : 239.0703, found: 239.0707.
1
5
12 3
CLN6. 4-Fluoro-2-hydroxyacetophenone (1.54 g, 10 mmol) 11 J. B. Daskiewicz, G. Comte, D. Barron, A. D. Pietro and
was dissolved in 2.5 mL of 95% ethanol solution, and 5 mL of F. Thomasson, Tetrahedron Lett., 1999, 40, 7095–7098.
0% potassium hydroxide aqueous solution was then added to 12 V. R. Yadav, S. Prasad, B. Sung and B. B. Aggarwal, Int.
4
ꢁ
the sample solution. The mixture was stirred for 10 min at 30 C
until all the solutes were dissolved to give a homogeneous 13 K. V. Sashidhara, A. Kumar, M. Kumar, J. Sarkar and
solution. Aer then, 2-hydroxybenzaldehyde (1.22 g, 10 mmol) S. Sinha, Bioorg. Med. Chem. Lett., 2010, 20, 7205–7211.
was dissolved in 2.5 mL of 95% ethanol and slowly added to the 14 L. B. Salum, W. F. Altei, L. D. Chiaradia, M. N. S. Cordeiro,
Immunopharmacol., 2011, 11, 295–309.
mixture. The resulting solution was then reuxed for 38 h. Aer
completion of the reaction, the pH was adjusted to 2 with dilute
R. R. Canevarolo, C. P. S. Melo, E. Winter, B. Mattei,
H. N. Daghestani, M. C. Santos-Silva, T. B. Creczynski-Pasa,
R. A. Yunes, J. A. Yunes, A. D. Andricopulo, B. W. Day,
R. J. Nunes and A. Vogt, J. Med. Chem., 2013, 63, 501–510.
hydrochloric acid and extracted with CH
organic layers were dried over anhydrous Na
2
Cl
2
. The combined
SO and evapo-
2
4
rated to dryness. CLN6 was isolated as a yellow solid through 15 B. Kolundzija, V. Markovic, T. Stanojkovic, L. Joksovic,
silica gel column chromatography with CH
2
Cl
2
as an eluent in
CN, 293 K)
I. Matic, N. Todorovic, M. Nikolic and M. D. Joksovic,
Bioorg. Med. Chem. Lett., 2014, 24, 65–71.
1
35% yield (0.90 g, 3.5 mmol). H NMR (500 MHz, CD
3
d (ppm): 13.35 (s, 1H), 8.18 (d, J ¼ 15.8 Hz, 1H), 8.16 (dd, J ¼ 7.8, 16 Y. L. N. Murthy, K. P. Suhasini, A. S. Pathania, S. Bhushan
5
1
2
1
.6 Hz, 1H), 7.84 (d, J ¼ 15.6 Hz, 1H), 7.74 (dd, J ¼ 7.8, 1.5 Hz,
and Y. N. Sastry, Eur. J. Med. Chem., 2013, 62, 545–555.
H), 7.67 (br, 1H), 7.32 (td, J ¼ 7.8, 1.5 Hz, 1H), 6.97 (td, J ¼ 7.4, 17 I. Karpaviciene, I. Cikotiene and J. M. Padron, Eur. J. Med.
.1 Hz, 1H), 6.96 (d, J ¼ 7.7 Hz, 1H), 6.76 (dd, J ¼ 8.8, 2.5 Hz,
Chem., 2013, 70, 568–578.
1
3
H), 6.72 (dd, J ¼ 10.6, 2.5 Hz); C NMR (125 MHz, CD
3
CN, 293 18 X. W. Zhou, H. L. Ma, X. Zhang, S. Y. Jing, J. Y. Miao and
K) d (ppm): 193.51, 156.85, 140.75, 133.17, 133.07, 132.49,
B. X. Zhao, Eur. J. Med. Chem., 2014, 79, 95–101.
1
1
29.53, 121.58, 120.44, 120.24, 116.26, 106.96, 106.77, 104.46, 19 V. Sharma, V. Kumar and P. Kumar, Anti-Cancer Agents Med.
ꢀ
04.27. HRMS (Orbitrap) m/z: [M ꢀ H] calculated for
Chem., 2013, 13, 422–432.
20 M. G. Jaroslaw, S. Olga and J. Janusz, Chem.–Eur. J., 2014, 20,
C H O F: 257.0608, found: 257.0615.
1
5
11 3
12790–12795.
2
2
2
2
2
2
1 R. B. Sushil, M. Bijan, V. Gonela and T. Arunabha, Inorg.
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Conflicts of interest
The authors declare no conict of interest.
Acknowledgements
The present work was sponsored by The National Natural
Science Foundation of China (21961026).
2006, 62, 765–770.
6 T. Viruthachalam, R. Perumal, T. Dhakshanamurthy and
T. R. Vayalakkavoor, Org. Lett., 2005, 7, 657–660.
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