Preview

Zhurnal Prikladnoii Spektroskopii

Advanced search

SYNTHESIS AND STRUCTURE OF α-AMINOPHOSPHATE AND ITS INTERACTION WITH DNA/BSA

Abstract

The reaction of terephthalaldehyde, p-chloroaniline, and diethyl phosphite in ethyl alcohol solution yields a new crystal (1), CCDC:1405044. This compound is characterized by X-ray single-crystal diffraction, IR, elemental analysis, ESI-MS, and 1H and 13C NMR. Compound 1 crystallizes in the triclinic system, space group P-1 with a = 11.0444(4) Å, b = 12.6468(4) Å, c = 12.7657(4) Å, V = 1627.46(9) Å3, Z = 2, C28H36Cl2N2O6P2, Mr = 629.43, Dc = 1.284 g/cm3, μ = 0.339 mm-1, F(000) = 660, GOOF = 1.101, final R = 0.0875 and wR = 0.1082 for 7381 observed reflections (I > 2σ(I)). The X-ray analysis reveals that the planes of p-chloroaniline and terephthalaldehyde form a dihedral angle of 87.54(0.28)°. In the crystal of compound 1, P atoms have tetrahedral geometries, made up by a double-bond O atom, one Cα atom, and two O-ethyl groups. Besides, Cα atoms are responsible for the existence of the optical activity. Five intramolecular hydrogen bonds helping to stabilize the crystal structure are observed. The interaction between compound 1 and DNA/BSA is also studied.

About the Authors

Y. L. Chen
Yancheng Teachers’ Unversity
China
Jiangsu, 224051


Q.-M. Wang
Yancheng Teachers’ Unversity
China
Jiangsu, 224051


References

1. W. M. Abdou, R. F. Barghash, M. S. Bekheit, Arch. Pharm. Chem. Life Sci., 345, 884–895 (2012).

2. E. D. Naydenova, P. T. Todorov, P. I. Mateeva, R. N. Zamfirova, N. D. Pavlov, S. B. Todorov, Amino Acids, 39, 1537–1543 (2010).

3. S. C. Fields, Tetrahedron, 55, 12237–12273 (2010).

4. F. R. Atherton, C. H. Hassall, R. W. Lambert, J. Med. Chem., 29, 29–40 (1986).

5. J. Z. Liu, B. A. Song, H. T. Fan, P. S. Bhadury, W. T. Wan, S. Yang, W. M. Xu, J.Wu, L. H. Jin, X. Wei, D. Y. Hu, S. Zeng, Eur. J. Med. Chem., 45, 5108–5112 (2010).

6. A. B. Smith, C. M. Taylor, S. J. Benkovic, R. Hirschmann, Tetrahedron Lett., 35, 6853–6856 (1994).

7. M. F. Abdel-Megeed, B. E. Badr, M. M. Azaam, G. A. El-Hiti, Bioorg. Med. Chem., 20, 2252–2258 (2012).

8. C. P. Holmes, X. F. Li, Y. J. Pan, C. D. Xu, A. Bhandari, C. M. Moody, J. A. Miguel, S. W. Ferla, M. N. De Francisco, B. T. Frederick, S. Q. Zhou, N. Macher, L. Jang, J. D. Irvine, J. R. Grove, Bioorg. Med. Chem. Lett., 18, 2719–2724 (2008).

9. A. Wahhab, D. Smil, A. Ajamian, M. Allan, Y. Chantigny, E. Therrien, N. Nguyen, S. Manku, S. Leit, J. Rahil, A. J. Petschner, A. H. Lu, A. Nicolescu, S. Lefebvre, S. Montcalm, M. Fournel, T. P. Yan, Z. M. Li, J. M. Besterman, R. Déziel, Bioorg. Med. Chem. Lett., 19, 336–340 (2009).

10. M. Thérien, K. Skorey, R. Zamboni R, C. S. Li, C. K. Lau, T. LeRiche, V. L. Truong, D. Waddleton, C. Ramachandran, Bioorg. Med. Chem. Lett., 14, 2319–2322 (2004).

11. Q. M. Wang, L. Yang, H. Ding, X. R. Chen, H. Wang, X. H. Tang, Bioorg. Chem., 69, 132–139 (2016).

12. Q. M. Wang, M. L. Zhu, R. T. Zhu, L. P. Lu, C. X. Yuan, S. Xing, X. Q. Fu, Y. H. Mei, Eur. J. Med. Chem., 49, 354–364 (2012).

13. B. M. Zeglis, V. C. Pierre, J. K. Barton, Chem. Commun., 44, 4565–4579 (2007).

14. C. Icsel, V. T. Yilmaz, Y. Kaya, S. Durmus, M. Sarimahmut, O. Buyukgungor, J. Inorg. Biochem., 152, 38–52 (2015).

15. A. I. Matesanz, C. Hernandez, A. Rodriguez, P. Souza, Dalton Trans., 40, 5738–5745 (2011).

16. E. R. Jamieson, S. J. Lippard, Chem. Rev., 99, 2467–2498 (1999).

17. L. Kelland, Nat. Rev. Cancer, 7, 573–584 (2007).

18. L. Ta, Neurotoxicology, 27, 992–1002 (2006).

19. S. Dhar, D. Senapati, P. K. Das, P. Chatopadhyay, M. Nethaji, A. R. Chakravarty, J. Am. Chem. Soc., 125, 12118–12124 (2003).

20. D. Li, J. Tian, Y. Kou, F. Huang, G. Chen, W. Gu, X. Liu, D. Liao, P. Cheng, S. Yan, Dalton Trans., 3574–3583 (2009).

21. L. S. Lerman, J. Mol. Biol., 3, 18–30 (1961).

22. W. Li, Y. H. Ji, C. X. Li, Z. Y. Liu, N. Li, L. Fang, J. Chang, J. Tan, World J. Gastroenterol., 22, No. 14, 3758–3768 (2016).

23. L. Cheng, C. Bulmer, A. Margaritis, Curr. Drug Deliv., 12, 351–357 (2015).

24. A. Robert, B. Meunier, Chem. Eur. J., 7, 1287–1296 (1998).

25. Q. M. Wang, W. Gao, J. L. Song, Y. Liu, H. Qi, X. H. Tang, J. Appl. Spectrosc., 83, No. 4, 703–709 (2016).

26. M. X. Li, M. L. Zhu, L. P. Lu, Acta Crystallogr., E64, o1178–o1179 (2008).

27. J. Rohovec, P. Vojtíšek, I. Lukeš, Phosphorus Sulfur Silicon Relat. Elem., 148, 79–95 (1999).

28. G. M. Sheldrick, Acta Crystallogr., A, 64, 112–122 (2008).

29. A. Gohel, M. B. McCarthy, G. Gronowicz, Endocrinology, 140, No. 11, 5339–5347 (1999).

30. J. K. Barton, J. M. Goldberg, C. V. Kumar, N. J. Turro, J. Am. Chem. Soc., 108, 2081–2088 (1986).

31. B. D. Wang, Z. Y. Yang, Q. Wang, T. K. Cai, P. Crewdson, Bioorg. Med. Chem., 14, No. 6, 1880–1888 (2006).

32. P. Grzegorz, Arch. Biochem. Biophys., 453, 54–62 (2006).

33. W. R. Ware, J. Phys. Chem., B, 66, 455–458 (1962).


Review

For citations:


Chen Y.L., Wang Q. SYNTHESIS AND STRUCTURE OF α-AMINOPHOSPHATE AND ITS INTERACTION WITH DNA/BSA. Zhurnal Prikladnoii Spektroskopii. 2019;86(5):842(1)-842(6).

Views: 362


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


ISSN 0514-7506 (Print)