Synthesis, Spectroscopic Properties of Boc-L-alanine Modified 1,8-Naphthyridine Ligands

Gaozhang Gou; Bo Zhou; Heping Yan; Na Wu; Shijuan Xu; Wei Liu

doi:10.14233/ajchem.2014.16507

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, Spectroscopic Properties of Boc-L-alanine Modified 1,8-Naphthyridine Ligands

https://doi.org/10.14233/ajchem.2014.16507

Gaozhang Gou

School of Science, Honghe University, Mengzi 661100, Yunnan Province, P.R. China; Key Laboratory of Natural Pharmaceutical & Chemical Biology of Yunnan Province, Mengzi 661100, Yunnan Province, P.R. China

Bo Zhou

School of Science, Honghe University, Mengzi 661100, Yunnan Province, P.R. China

Heping Yan

School of Science, Honghe University, Mengzi 661100, Yunnan Province, P.R. China

Na Wu

School of Science, Honghe University, Mengzi 661100, Yunnan Province, P.R. China

Shijuan Xu

School of Science, Honghe University, Mengzi 661100, Yunnan Province, P.R. China

Wei Liu

Corresponding Author(s) : Wei Liu

liuwei4728@126.com

Asian Journal of Chemistry, Vol. 26 No. 21 (2014): Vol 26 Issue 21
Article Published : September 30, 2014

Abstract

Two 1,8-naphthyridine derivatives containing amino acid by amido bond, Boc-L-alanine-2-methy-1,8-naphthyridine (L1) and Boc-L-alanine-2,4-dimethy-1,8-naphthyridine (L2) were synthesized and characterized. And there absorption and fluorescence spectra in various solvents and solid are presented comprehensively. The two ligands exhibit similar electronic absorption spectra with l_max at about 330 nm, which can be tentatively assigned to p®p^* transition. A comprehensive study of spectroscopic properties upon titration of L1, L2 with HBF₄ as a proton source in CH₃OH was investigated. Compounds L1 and L2 can use as acid-controlled molecular switching on from the luminescence intensity change caused by proton source.

Keywords

Boc-L-alanine Amino acid Acid-controlled molecular switching on 1,8-Naphthyridine derivatives Spectroscopic properties

Gou, G., Zhou, B., Yan, H., Wu, N., Xu, S., & Liu, W. (2014). Synthesis, Spectroscopic Properties of Boc-L-alanine Modified 1,8-Naphthyridine Ligands. Asian Journal of Chemistry, 26(21), 7109–7112. https://doi.org/10.14233/ajchem.2014.16507

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References

J.K. Bera, N. Sadhukhan and M. Majumdar, Eur. J. Inorg. Chem., 2009, 4023 (2009); doi:10.1002/ejic.200900312.
V. Litvinov, Adv. Heterocycl. Chem., 91, 189 (2006); doi:10.1016/S0065-2725(06)91004-6.
W.W. Paudler and R.M. Sheets, Adv. Heterocycl. Chem., 33, 147 (1983); doi:10.1016/S0065-2725(08)60053-7.
M. Andrews, R.H. Laye and S.J. Pope, Transition Metal Chem., 34, 493 (2009); doi:10.1007/s11243-009-9221-0.
V.P. Litvinov, S.V. Roman and V.D. Dyachenko, Russ. Chem. Rev., 69, 201 (2000); doi:10.1070/RC2000v069n03ABEH000553.
H. Araki, K. Tsuge, Y. Sasaki, S. Ishizaka and N. Kitamura, Inorg. Chem., 46, 10032 (2007); doi:10.1021/ic7010925.
C.X. Wang, Y. Sato, M. Kudo, S. Nishizawa and N. Teramae, Chem. Eur. J., 18, 9481 (2012); doi:10.1002/chem.201200219.
Z. Li, W. Zhao, X. Li, Y. Zhu, C. Liu, L. Wang, M. Yu, L. Wei, M. Tang and H. Zhang, Inorg. Chem., 51, 12444 (2012); doi:10.1021/ic3018453.
Y. Zhou, Y. Xiao and X. Qian, Tetrahedron Lett., 49, 3380 (2008); doi:10.1016/j.tetlet.2008.03.128.
Y. Ferrand, A.M. Kendhale, J. Garric, B. Kauffmann and I. Huc, Angew. Chem., 122, 1822 (2010); doi:10.1002/ange.200906401.
S.Z. Hu and C.F. Chen, Chem. Commun., 46, 4199 (2010); doi:10.1039/c002944k.
Q. Gan, Y. Ferrand, N. Chandramouli, B. Kauffmann, C. Aube, D. Dubreuil and I. Huc, J. Am. Chem. Soc., 134, 15656 (2012); doi:10.1021/ja3064364.
H. Yamazaki, T. Hakamata, M. Komi and M. Yagi, J. Am. Chem. Soc., 133, 8846 (2011); doi:10.1021/ja2024228.
H.W. Tseng, R. Zong, J.T. Muckerman and R. Thummel, Inorg. Chem., 47, 11763 (2008); doi:10.1021/ic8014817.
D. Bhuniya, D. Umrani, B. Dave, D. Salunke, G. Kukreja, J. Gundu, M. Naykodi, N.S. Shaikh, P. Shitole, S. Kurhade, S. De, S. Majumdar, S.B. Reddy, S. Tambe, Y. Shejul, A. Chugh, V.P. Palle, K.A. Mookhtiar, D. Cully, J. Vacca, P.K. Chakravarty, R.P. Nargund, S.D. Wright, M.P. Graziano, S.B. Singh, S. Roy and T.-Q. Cai, Bioorg. Med. Chem. Lett., 21, 3596 (2011); doi:10.1016/j.bmcl.2011.04.091.
A. Capozzi, E. Mantuano, P. Matarrese, G. Saccomanni, C. Manera, V. Mattei, L. Gambardella, W. Malorni, M. Sorice and R. Misasi, Anticancer Agents Med. Chem., 12, 653 (2012); doi:10.2174/187152012800617731.
Y. Chen, J.L. Li, G.S.M. Tong, W. Lu, W.-F. Fu, S.-W. Lai and C.-M. Che, Chem. Sci., 2, 1509 (2011); doi:10.1039/c0sc00597e.
A. Fernández-Mato, J.M. Quintela and C. Peinador, New J. Chem., 36, 1634 (2012); doi:10.1039/c2nj40279c.
Y.Y. Wu, Y. Chen, G.Z. Gou, W.-H. Mu, X.-J. Lv, M.-L. Du and W.-F. Fu, Org. Lett., 14, 5226 (2012); doi:10.1021/ol302347m.
G. Ligthart, H. Ohkawa, R.P. Sijbesma and E.W. Meijer, J. Org. Chem., 71, 375 (2006); doi:10.1021/jo051864b.
C.A. Anderson, P.G. Taylor, M.A. Zeller and S.C. Zimmerman, J. Org. Chem., 75, 4848 (2010); doi:10.1021/jo100476x.
W.F. Fu, L.F. Jia, W.H. Mu, X. Gan, J.-B. Zhang, P.-H. Liu, Q.-Y. Cao, G.-J. Zhang, L. Quan, X.-J. Lv and Q.-Q. Xu, Inorg. Chem., 49, 4524 (2010); doi:10.1021/ic100094y.
S.M. Chi, Y.F. Wang, X. Gan, D.-H. Wang and W.-F. Fu, Cent. Eur. J. Chem., 7, 923 (2009); doi:10.2478/s11532-009-0087-y.
C. He, J.L. DuBois, B. Hedman, K.O. Hodgson and S.J. Lippard, Angew. Chem. Int. Ed., 40, 1484 (2001); doi:10.1002/1521-3773(20010417)40:8<1484::AID-ANIE1484>3.0.CO;2-Z.
R.A. Henery and P.R. Hammond, J. Heterocycl. Chem., 14, 1109 (1977); doi:10.1002/jhet.5570140638.
Y. Chen, W.F. Fu, J.L. Li, X.-J. Zhao and X.-M. Ou, New J. Chem., 31, 1785 (2007); doi:10.1039/b705149b.
E.V. Brown, J. Org. Chem., 30, 1607 (1965); doi:10.1021/jo01016a066.
W.W. Paudler and T.J. Kress, J. Org. Chem., 32, 832 (1967); doi:10.1021/jo01278a078.
Z. Li, M. Yu, L. Zhang, M. Yu, J. Liu, L. Wei and H. Zhang, Chem. Commun., 46, 7169 (2010); doi:10.1039/c0cc01687j.

References

J.K. Bera, N. Sadhukhan and M. Majumdar, Eur. J. Inorg. Chem., 2009, 4023 (2009); doi:10.1002/ejic.200900312.

V. Litvinov, Adv. Heterocycl. Chem., 91, 189 (2006); doi:10.1016/S0065-2725(06)91004-6.

W.W. Paudler and R.M. Sheets, Adv. Heterocycl. Chem., 33, 147 (1983); doi:10.1016/S0065-2725(08)60053-7.

M. Andrews, R.H. Laye and S.J. Pope, Transition Metal Chem., 34, 493 (2009); doi:10.1007/s11243-009-9221-0.

V.P. Litvinov, S.V. Roman and V.D. Dyachenko, Russ. Chem. Rev., 69, 201 (2000); doi:10.1070/RC2000v069n03ABEH000553.

H. Araki, K. Tsuge, Y. Sasaki, S. Ishizaka and N. Kitamura, Inorg. Chem., 46, 10032 (2007); doi:10.1021/ic7010925.

C.X. Wang, Y. Sato, M. Kudo, S. Nishizawa and N. Teramae, Chem. Eur. J., 18, 9481 (2012); doi:10.1002/chem.201200219.

Z. Li, W. Zhao, X. Li, Y. Zhu, C. Liu, L. Wang, M. Yu, L. Wei, M. Tang and H. Zhang, Inorg. Chem., 51, 12444 (2012); doi:10.1021/ic3018453.

Y. Zhou, Y. Xiao and X. Qian, Tetrahedron Lett., 49, 3380 (2008); doi:10.1016/j.tetlet.2008.03.128.

Y. Ferrand, A.M. Kendhale, J. Garric, B. Kauffmann and I. Huc, Angew. Chem., 122, 1822 (2010); doi:10.1002/ange.200906401.

S.Z. Hu and C.F. Chen, Chem. Commun., 46, 4199 (2010); doi:10.1039/c002944k.

Q. Gan, Y. Ferrand, N. Chandramouli, B. Kauffmann, C. Aube, D. Dubreuil and I. Huc, J. Am. Chem. Soc., 134, 15656 (2012); doi:10.1021/ja3064364.

H. Yamazaki, T. Hakamata, M. Komi and M. Yagi, J. Am. Chem. Soc., 133, 8846 (2011); doi:10.1021/ja2024228.

H.W. Tseng, R. Zong, J.T. Muckerman and R. Thummel, Inorg. Chem., 47, 11763 (2008); doi:10.1021/ic8014817.

D. Bhuniya, D. Umrani, B. Dave, D. Salunke, G. Kukreja, J. Gundu, M. Naykodi, N.S. Shaikh, P. Shitole, S. Kurhade, S. De, S. Majumdar, S.B. Reddy, S. Tambe, Y. Shejul, A. Chugh, V.P. Palle, K.A. Mookhtiar, D. Cully, J. Vacca, P.K. Chakravarty, R.P. Nargund, S.D. Wright, M.P. Graziano, S.B. Singh, S. Roy and T.-Q. Cai, Bioorg. Med. Chem. Lett., 21, 3596 (2011); doi:10.1016/j.bmcl.2011.04.091.

A. Capozzi, E. Mantuano, P. Matarrese, G. Saccomanni, C. Manera, V. Mattei, L. Gambardella, W. Malorni, M. Sorice and R. Misasi, Anticancer Agents Med. Chem., 12, 653 (2012); doi:10.2174/187152012800617731.

Y. Chen, J.L. Li, G.S.M. Tong, W. Lu, W.-F. Fu, S.-W. Lai and C.-M. Che, Chem. Sci., 2, 1509 (2011); doi:10.1039/c0sc00597e.

A. Fernández-Mato, J.M. Quintela and C. Peinador, New J. Chem., 36, 1634 (2012); doi:10.1039/c2nj40279c.

Y.Y. Wu, Y. Chen, G.Z. Gou, W.-H. Mu, X.-J. Lv, M.-L. Du and W.-F. Fu, Org. Lett., 14, 5226 (2012); doi:10.1021/ol302347m.

G. Ligthart, H. Ohkawa, R.P. Sijbesma and E.W. Meijer, J. Org. Chem., 71, 375 (2006); doi:10.1021/jo051864b.

C.A. Anderson, P.G. Taylor, M.A. Zeller and S.C. Zimmerman, J. Org. Chem., 75, 4848 (2010); doi:10.1021/jo100476x.

W.F. Fu, L.F. Jia, W.H. Mu, X. Gan, J.-B. Zhang, P.-H. Liu, Q.-Y. Cao, G.-J. Zhang, L. Quan, X.-J. Lv and Q.-Q. Xu, Inorg. Chem., 49, 4524 (2010); doi:10.1021/ic100094y.

S.M. Chi, Y.F. Wang, X. Gan, D.-H. Wang and W.-F. Fu, Cent. Eur. J. Chem., 7, 923 (2009); doi:10.2478/s11532-009-0087-y.

C. He, J.L. DuBois, B. Hedman, K.O. Hodgson and S.J. Lippard, Angew. Chem. Int. Ed., 40, 1484 (2001); doi:10.1002/1521-3773(20010417)40:8<1484::AID-ANIE1484>3.0.CO;2-Z.

R.A. Henery and P.R. Hammond, J. Heterocycl. Chem., 14, 1109 (1977); doi:10.1002/jhet.5570140638.

Y. Chen, W.F. Fu, J.L. Li, X.-J. Zhao and X.-M. Ou, New J. Chem., 31, 1785 (2007); doi:10.1039/b705149b.

E.V. Brown, J. Org. Chem., 30, 1607 (1965); doi:10.1021/jo01016a066.

W.W. Paudler and T.J. Kress, J. Org. Chem., 32, 832 (1967); doi:10.1021/jo01278a078.

Z. Li, M. Yu, L. Zhang, M. Yu, J. Liu, L. Wei and H. Zhang, Chem. Commun., 46, 7169 (2010); doi:10.1039/c0cc01687j.

Issue

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

Synthesis, Spectroscopic Properties of Boc-L-alanine Modified 1,8-Naphthyridine Ligands

Corresponding Author(s) : Wei Liu

Abstract

Keywords

Full Article

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