Synthesis of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole amino acid Derivatives and Anti-DNA Damaging Activity

Ranganatha S.R; Vinaya K; Chandrappa S.; Ananda Kumar C. S.; Benaka Prasad S. B; Prasanna D.S; Rangappa K.S.

doi:10.37285/ijddd.1.1.7

Articles

Vol. 1 No. 1 (2010): January-March 2010

Synthesis of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole amino acid Derivatives and Anti-DNA Damaging Activity

Ranganatha S.R^▸^▾
Vinaya K^▸^▾
Chandrappa S.^▸^▾
Ananda Kumar C. S.^▸^▾
Benaka Prasad S. B^▸^▾
Prasanna D.S^▸^▾
Rangappa K.S.^▸^▾

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DOI: https://doi.org/10.37285/ijddd.1.1.7
Submitted: November 19, 2024
Published: 2010-02-15

Abstract

Series of novel 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole L-amino acid derivatives 5(a-f) were synthesized by varying substitution at N-position of the 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole. All the compounds 5(a-f) were characterized by 1H-NMR, IR and LC/MS spectroscopy. The compounds were tested for anti-DNA damaging property by using biophysical techniques such as agarose gel, thermal melting temperature (Tm) and ethidium bromide binding to DNA by using fluorescence spectrophotometer. The results revealed that 5c, 5b and 5d showed high activity. These observations can be related to the presence of the lysine, tryptophan and proline amino acid residues with basic amine, aromatic and heterocyclic groups respectively.

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Keywords

1,2-benzisoxazole
Amino acids
Alzheimer’s disease
Anti-DNA damage

How to Cite

S.R, R., K, V., S., C., C. S., A. K., S. B, B. P., D.S, P., & K.S., R. (2010). Synthesis of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole amino acid Derivatives and Anti-DNA Damaging Activity . International Journal of Drug Design and Discovery, 1(1), 57–64. https://doi.org/10.37285/ijddd.1.1.7

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[1] 1. Van Muiswinkel, F.L.; Kuiperij, H.B.; The. Curr. Drug. Targets. CNS. Neurol. Disord. 2005, 4, 267.

[2] 2. Frautschy, S.A.; Baired, A.; Cole, G.M.; Ann. N. Y. Acad. Sci. USA. 1991, 88, 8362.

[3] 3. Markesbery, W.R.; Free. Radic. Biol. Med. 1997, 23, 134.

[4] 4. Mancuso, M.; Coppede, F.; Migliore, L.; Siciliano, G.; Murri, L.; J. Alzheimers. Dis. 2006, 10, 59.

[5] 5. Evans, M.D.; Dizdaroglu, M.; Cooke, M.S.; Mutat. Res. 2004, 567, 1.

[6] 6. Lin, M.T.; Beal, M.F.; Nature. 2006, 443, 787.

[7] 7. Kirk, K.L.; Filler, R.; In Biomedical Frontiers of Fluorine Chemistry, Symposium Series; American Chemical Society, Washington, DC, 1996, 639, 1.

[8] 8. Kuhl, A.; Hahn, M.G.; Dumic, M.; Mittendorf, J.; Amino. Acids. 2005, 29, 89.

[9] 9. Richard, P.; Cheng.; Samuel, H.; Gellman.; DeGrado,

[10] W. F.; Chem. Rev. 2001, 101, 3219.

[11] 10. Yan, S.; Larson, G.; Wu, J.Z.; App leby, T.; Ding, Y.; Hamatake, R, Hong, Z.; Yao, N.; Bioorg. Med. Chem. Lett. 2007, 17, 1991.

[12] 12. Dublanchet, A.C.; Ducrot, P.; Andrianjara, C.; Gara, M.O.; Morales, R.; Compere, D.; Denis, A.; Blais, S.; Cluzeau, P.; Courte, K.; Hamon, J.; Moreau, F.; Prunet, M. L.; Tertre, A.; Bioorg. Med. Chem. Lett. 2005, 15, 3787.

[13] 13. Cardillo, G.; Gentilucci, L.; Melchiorre, P.; Spampinato, S.; Bioorg. Med. Chem. Lett. 2000, 10, 2755.

[14] 14. Jin, M.; Fischbach, M.A.; Clardy, J.; J. Am. Chem. Soc. 2006, 128, 10660.

[15] 15. Marcuse, R.; J. Am. Oil. Chem. Soc. 1962, 39, 97.

[16] 16. Arredondo, M.; Nunez, M.T.; Mol. Aspects. Med. 2005, 26, 313.

[17] 17. Floris, G.; Agro, A.F.; Amine Oxidases. In: Lennarz WJ, Lane MD (ed) Encyclopedia of Biological Chemistry, Elsevier Inc, 2004, 1, pp 85.

[18] 18. Halliwell, B.; Adv. Pharmacol. 1997, 38, 3.

[19] 19. Lovell, M.A.; Ehmann, W.D.; Butler, S.M.; Markesberg,W. R.; Neurology. 1995, 45, 1594.

[20] 20. Pappolla, M.A.; Chyan, Y.J.; Omar, R.A.; Hsiao, K.; Perry, G.; Smith, M.A.; Bozner, P.; Am. J. Pathol. 1998, 152, 871.

[21] 21. Barbara, S.; Berlett.; Stadtman, E.R.; J. Biol. Chem. 1997, 272, 20313.

[22] 22. Amici, A.; Levine, R.L.; Tsai, L.; Stadtman, E.R.; J. Biol. Chem. 1989, 264, 3341.

[23] 23. Armstrong, R.C.; Swallow, A.J.; Radiation. Res. 1969, 41, 563.

[24] 24. Uchida, K.; Kato, Y.; Kawakishi, S.; Biochem. Biophys. Res. Commun. 1990, 169, 265.

[25] 25. Basappa.; Mantelingu, K.; Sadashiva, M.P.; Rangappa,K. S.; Indian. J. Chem. 2004, 43, 1954.

[26] 26. Scatchard, G.; Ann. N. Y. Acad. Sci. USA. 1949, 51,660.