Chen 2011
Chen 2011
Chen 2011
Abstract
To develop more potent small molecules with enhanced free radical scavenger properties, a series of N-substituted
isatin derivatives was synthesized, and the cytoprotective effect on the apoptosis of PC12 cells induced by H2O2
was screened. All these compounds were found to be active, and N-ethyl isatin was found with the most potent
activity of 69.7% protective effect on PC12 cells. Structure-activity relationship analyses showed the bioactivity of N-
alkyl isatins decline as the increasing of the chain of the alkyl group, furthermore odd-even effect was found in the
activity, which is interesting for further investigation.
© 2010 Chen et al
Chen et al. Chemistry Central Journal 2011, 5:37 Page 2 of 5
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80
70 20 μM
.
20 μM
60
Protective effect(%)
50
40
30
20
10
0
1 2 3 4 5 6
Alkyl-carbon atom amount of the substituent
Figure 1 The cytoprotective activities of N-substituted isatin derivatives with the alkyl group containing 1-6 carbon atoms (The
corresponding compounds are compounds 2-7.).
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Found: C, 68.59; H, 5.22; N, 8.01 (%). Calc. for 1.2 Hz), 7.56 (1 H, dd, J = 7.6, 1.2 Hz), 7.29 (1 H, d, J =
(C10H9NO2): C, 68.56; H, 5.18; N, 8.00 (%). 8.0 Hz), 7.14 (1 H, dd, J = 7.6, 0.8 Hz), 4.10 (2 H, t, J =
1-Propylindoline-2,3-dione (Compound 4) 1 H-NMR 6.4 Hz), 3.70 (2 H, t, J = 6.4 Hz); MS (EI) m/z: 211 (M
(D6-DMSO, 400 MHz): 7.58 (1 H, d, J = 6.8 Hz), 7.55 (1 +
); Anal. Found: C, 58.86; H, 3.99; N, 13.70 (%). Calc.
H, t, J = 7.6 Hz), 7.09 (1 H, t, J = 7.6 Hz), 6.88 (1 H, d, J for (C10H8ClNO2): C, 58.82; H, 3.95; N, 13.72 (%).
= 8 Hz), 3.67 (2 H, t, J = 7.2 Hz), 1.72 (2 H, m, J = 7.2- 1-(2-Bromoethyl)indoline-2,3-dione (Compound 12)
7.6 Hz), 0.98 (3 H, t, J = 7.6 Hz); MS (EI) m/z: 189 (M 1
H-NMR (D6-DMSO, 400 MHz) δ: 7.67 (1 H, td, J = 8,
+
); Anal. Found: C, 69.88; H, 5.89; N, 7.35 (%). Calc. for 1.2 Hz), 7.57 (1 H, dd, J = 7.6, 1.2 Hz), 7.29 (1 H, d, J =
(C11H11NO2): C, 69.83; H, 5.86; N, 7.40 (%). 8.0 Hz), 7.14 (1 H, dd, J = 7.6, 0.8 Hz), 4.11 (2 H, t, J =
1-Butylindoline-2,3-dione (Compound 5) 1 H-NMR 6.4 Hz), 3.71 (2 H, t, J = 6.4 Hz); MS (EI) m/z: 254 (M
(CDCl3, 400 MHz) δ: 7.60 (2 H, m), 7.12 (1 H, t, J = 7.6 +
); Anal. Found: C, 47.31; H, 3.19; N, 5.50 (%). Calc. for
Hz), 6.91 (1 H, d, J = 8.4 Hz), 3.73 (2 H, t, J = 7.6 Hz), (C10H8BrNO2): C, 47.27; H, 3.17; N, 5.51 (%).
1.69 (2 H, m), 1.42 (2 H, m), 0.98 (3 H, t, J = 7.2 Hz);
MS (EI) m/z: 203 (M+); Anal. Found: C, 70.90; H, 6.59;
Acknowledgements
N, 6.90 (%). Calc. for (C12H13NO2): C, 70.92; H, 6.54; N, This work was financially supported by the grant from Scientific Research
6.89 (%). Program Funded by Shaanxi Provincial Education Department (Program
1-Pentylindoline-2,3-dione (Compound 6) 1 H-NMR No.11JK0560).
(CDCl3, 400 MHz) δ: 7.60 (2 H, m), 7.12 (1 H, t, J = 7.6 Author details
Hz), 6.91 (1 H, d, J = 8.0 Hz), 3.72 (2 H, t, J = 7.6 Hz), 1
College of Chemistry and Chemical Engineering, Xi’an Shiyou University,
1.71 (2 H, m), 1.37 (4 H, m), 0.91 (3 H, t, J = 6.8 Hz); Xi’an, Shaanxi, 710065, PR China. 2Key Laboratory of Chemistry for Natural
Products of Guizhou Province and Chinese Academy of Sciences, Guiyang
MS (EI) m/z: 217 (M+); Anal. Found: C, 71.88; H, 7.00; 550002, PR China.
N, 6.44 (%). Calc. for (C13H15NO2): C, 71.87; H, 6.96; N,
6.45 (%). Authors’ contributions
GC has formulated the research idea and prepared the manuscript draft
1-Hexylindoline-2,3-dione (Compound 7) 1 H-NMR version, YW prepared the manuscript for submission and coordinated further
(CDCl3, 400 MHz) δ: 7.60 (2 H, m), 7.11 (1 H, t, J = 7.6 formalities, SM and QS carried out the chemical and biological studies, XH
Hz), 6.90 (1 H, d, J = 7.6 Hz), 3.72 (2 H, t, J = 7.6 Hz), conceived of the study, participated in its design and coordination. All
authors have read and approved the final manuscript.
1.70 (2 H, m), 1.31-1.38 (6 H, m), 0.89 (3 H, t, J = 6.4
Hz); MS (EI) m/z: 231 (M+); Anal. Found: C, 72.72; H, Competing interests
7.40; N, 6.01 (%). Calc. for (C14H17NO2): C, 72.70; H, The authors declare that they have no competing interests.
7.41; N, 6.06 (%). Received: 19 April 2011 Accepted: 1 July 2011 Published: 1 July 2011
1-Allylindoline-2,3-dione (Compound 8) 1 H-NMR
(D6-DMSO, 400 MHz): 7. 63 (1 H, t, J = 7.6 Hz), 7.55 (1 References
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Chen et al. Chemistry Central Journal 2011, 5:37 Page 5 of 5
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doi:10.1186/1752-153X-5-37
Cite this article as: Chen et al.: Simple isatin derivatives as free radical
scavengers: Synthesis, biological evaluation and structure-activity
relationship. Chemistry Central Journal 2011 5:37.