Synthesis, Characterization, Crystal Structure and Free Radical Scavenging Activities of 2-(2-Benzylamine)-6-[(2-benzylamine)amino]-5-nitro-1H-benzo[de]-isoquinoline-1,3(2H)-dione

Ye Zhang; Wen Qin; Yongzhi Liao; Xianghui Yi

doi:10.14233/ajchem.2014.17444

Issue

Vol. 26 No. 21 (2014): Vol 26 Issue 21

Issue Published : September 30, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis, Characterization, Crystal Structure and Free Radical Scavenging Activities of 2-(2-Benzylamine)-6-[(2-benzylamine)amino]-5-nitro-1H-benzo[de]-isoquinoline-1,3(2H)-dione

https://doi.org/10.14233/ajchem.2014.17444

Ye Zhang

Department of Chemistry & Pharmaceutical Science, Guilin Normal College, Guilin 541001, Guangxi Province, P.R. China

Wen Qin

Department of Chemistry & Pharmaceutical Science, Guilin Normal College, Guilin 541001, Guangxi Province, P.R. China

Yongzhi Liao

Guangxi Academy of Fishery Sciences, Nanning 530021, P.R. China

Xianghui Yi

Department of Chemistry & Pharmaceutical Science, Guilin Normal College, Guilin 541001, Guangxi Province, P.R. China

Corresponding Author(s) : Yongzhi Liao

liao0777@163.com

Asian Journal of Chemistry, Vol. 26 No. 21 (2014): Vol 26 Issue 21
Article Published : October 1, 2014

Abstract

2-(2-Benzylamine)-6-[(2-benzylamine)amino]-5-nitro-1H-benzo[de]-isoquinoline-1,3(2H)-dione (BBNID, 3) was synthesized and then characterized by FT-IR, NMR and elemental analysis. The crystal structure of BBNID was investigated using X-ray diffraction and SHELXTL97 software and the result indicated that BBNID crystallized in the monoclinic system, space group C2/c with a = 8.8032 (14), b = 8.822 (2), c = 13.994 (4) Å, V = 1005.9 (4) Å³; Z = 2. The free radical scavenging activity screening results showed that BBNID exhibited better scavenging activity than the commercial antioxidant BHT against 2,2-diphenyl-1-picrylhydrazyl radical (DPPH^•), with IC₅₀ of 43.10 μM.

Keywords

Naphthalimides Synthesis Crystal Free radical scavenging activity

Zhang, Y., Qin, W., Liao, Y., & Yi, X. (2014). Synthesis, Characterization, Crystal Structure and Free Radical Scavenging Activities of 2-(2-Benzylamine)-6-[(2-benzylamine)amino]-5-nitro-1H-benzo[de]-isoquinoline-1,3(2H)-dione. Asian Journal of Chemistry, 26(21), 7460–7462. https://doi.org/10.14233/ajchem.2014.17444

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References

C. Behl, Int. J. Vitam. Nutr. Res., 69, 213 (1999); doi:10.1024/0300-9831.69.3.213.

B. Halliwell and J.M.C. Gutteridge, Free Radicals in Biology and Medicine, Oxford University Press: Oxford (1999).

T.W. Stief, Med. Hypotheses, 60, 567 (2003); doi:10.1016/S0306-9877(03)00026-4.

B.N. Ames, M.K. Shigenaga and T.M. Hagen, Proc. Natl. Acad. Sci. USA, 90, 7915 (1993); doi:10.1073/pnas.90.17.7915.

Y.K. Tyagi, A. Kumar, H.G. Raj, P. Vohra, G. Gupta, R. Kumari, P. Kumar and R.K. Gupta, Eur. J. Med. Chem., 40, 413 (2005); doi:10.1016/j.ejmech.2004.09.002.

A. Kamal, B.S.N. Reddy, G.S.K. Reddy and G. Ramesh, Bioorg. Med. Chem. Lett., 12, 1933 (2002); doi:10.1016/S0960-894X(02)00326-8.

M.F. Braña, M. Cacho, A. Ramos, M. Teresa Domínguez, J.M. Pozuelo, C. Abradelo, M. Fernanda Rey-Stolle, M. Yuste, C. Carrasco and C. Bailly, Org. Biomol. Chem., 1, 648 (2003); doi:10.1039/b209042b.

M.F. Braña and A. Ramos, Curr. Med. Chem. Anticancer Agents, 1, 237 (2001); doi:10.2174/1568011013354624.

V.K. Malviya, P.Y. Liu, D.S. Alberts, E.A. Surwit, J.B. Craig and E.V. Hannigan, Am. J. Clin. Oncol., 15, 41 (1992); doi:10.1097/00000421-199202000-00009.

Y. Zhang, S.B. Feng, Q. Wu, K. Wang, X.H. Yi, H.S. Wang and Y.M. Pan, Med. Chem. Res., 20, 752 (2011); doi:10.1007/s00044-010-9384-4.

Y. Zhang, B.Q. Zou, K. Wang, Y.M. Pan, H. Liang, X.H. Yi and H.S. Wang, Med. Chem. Res., 21, 1341 (2012); doi:10.1007/s00044-011-9648-7.

Y. Zhang, G.M. Han, Q. Wu and H.S. Wang, Acta Crystallogr., E63, o4336 (2007); doi:10.1107/S1600536807049975.

Y.L. Lee, M.T. Yen and J.L. Mau, Food Chem., 104, 1 (2007); doi:10.1016/j.foodchem.2006.10.063.

Issue

Vol. 26 No. 21 (2014): Vol 26 Issue 21

Synthesis, Characterization, Crystal Structure and Free Radical Scavenging Activities of 2-(2-Benzylamine)-6-[(2-benzylamine)amino]-5-nitro-1H-benzo[de]-isoquinoline-1,3(2H)-dione

Corresponding Author(s) : Yongzhi Liao

Abstract

Keywords

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