Optimized Synthesis and Spectral Characterization of Some Hydrazones Based on 5-Nitroindazole with Pharmacological Potential

Authors

  • C. Cheptea “Gr. T. Popa” University of Medicine and Pharmacy, Faculty of Medical Bioengineering
  • L. M. Ivan ”Al. I. Cuza” University, Faculty of Physics
  • D. O. Dorohoi ”Al. I. Cuza” University, Faculty of Physics
  • V. Sunel “Al. I. Cuza” University, Faculty of Chemistry
  • I. Hurjui “Gr. T. Popa” University of Medicine and Pharmacy, Faculty of Medicine
  • C. I. Saveanu “Gr. T. Popa” University of Medicine and Pharmacy, Faculty of Dental Medicine
  • A. I. Galaction “Gr. T. Popa” University of Medicine and Pharmacy, Faculty of Medical Bioengineering

DOI:

https://doi.org/10.15407/ujpe59.03.0313

Keywords:

Hydrazones, HyperChem, antitumor effect

Abstract

A number of new hydrazones with biological activity are synthesized on the basis of 5-nitroindazole. The most efficient conditions of their synthesis with maximum reaction yield are established. The chemical structure of new compounds is found by the elemental analysis, FTIR spectroscopy, and 1H-NMR method. The data of spectral analysis were verified by calculations with the HyperChem software. Toxicological tests indicate that the synthesized hydrazones have the antitumor effect.

References

J.-H. Sun, C.A. Teleha, J.-S. Yan, J.D. Rodgers, and D.A. Nugiel, J. Org. Chem. 62, 5627 (1997).

https://doi.org/10.1021/jo970375b

J.D. Rodgers, B.L. Johnson, H. Wang, R.A. Greenberg, S. Erickson-Viitanen, R.M. Klabe, B.C. Cordova, M.M. Rayner, G.N. Lam, and C.-H. Chang, Bioorg. Med. Chem. Lett. 6, 2919 (1996).

https://doi.org/10.1016/S0960-894X(96)00531-8

M.H. Norman, F. Navas, J.B. Thompson, G.C. Rigdon, J. Med. Chem. 39, 4692 (1996).

https://doi.org/10.1021/jm9603375

T. Yoshida, N. Matsuura, K. Yamamoto, M. Doi, K. Shimada, T. Morie, and S. Kato, Heterocycles 43, 2701 (1996).

https://doi.org/10.3987/COM-96-7614

D.W. Robertson, W. Bloomquist, M.L. Cohen, L.R. Reid, K. Schenck, and D.T. Wong, J. Med. Chem. 33, 3176 (1990).

https://doi.org/10.1021/jm00174a013

B.K. Keppler and M. Hartmann, Met. Based Drugs 1, 145 (1994).

https://doi.org/10.1155/MBD.1994.145

X. Li, S. Chu, V.A. Feher, M. Khalili, Z. Nie, S. Margosiak, V. Nikulin, J. Levin, K.G. Sprankle, M.E. Tedder, R. Almassy, K. Appelt, and K.M. Yager, J. Med. Chem. 46, 5663 (2003).

https://doi.org/10.1021/jm0302039

J. Rodriguez, A. Gerpe, G. Aguirre, U. Kemmerling, O. Piro, V. Ar’an, J. Maya, C.O. Azar, M. Gonz’ales, and H. Cerecetto, Eur. J. Med. Chem. 44, 1545 (2009).

https://doi.org/10.1016/j.ejmech.2008.07.018

L. Bouissoine, S. Kazzouli, L. Pfeiffer, E.M. Rakis, M. Khouili, and G. Guillaumet, Bioorg. Med. Chem. 14, 1078 (2006).

https://doi.org/10.1016/j.bmc.2005.09.037

Wei Li, Yan Lu, Z. Wang, J.T. Dalton, and D.D. Miller, Bioorg. Med. Chem. Lett. 17, 4113 (2007).

https://doi.org/10.1016/j.bmcl.2007.05.059

T. Yakaian, V.P. Lingaiah, B. Naraian, B. Shidhar, Bioorg. Med. Chem. 17, 3445 (2007).

https://doi.org/10.1016/j.bmcl.2007.03.087

L.J. Huang, M.L. Shih, H.S. Chen, S.L. Pan, C.M. Teng, F.Y. Lee, and S.C. Kuo, Bioorg Med. Chem. 14, 528 (2006).

https://doi.org/10.1016/j.bmc.2005.08.032

M. Ribeira, J. Cabral, and A. Cimas, J. Chem. Thermodyn. 42, 1240 (2010).

https://doi.org/10.1016/j.jct.2010.04.026

A. Gerpe, G. Aguirre, L. Boiani, H. Cerecetto, M. Gonz’ales, C.O. Azar, C. Riogol, J. Maya, A. Morello, O. Piro, V. Ar’an, A. Azqueta, A. Cer’ain, A. Monge, A. M. Rojas, and G. Yalluf, Bioorg. Med. Chem. 14, 3467 (2006).

https://doi.org/10.1016/j.bmc.2006.01.007

M. Alho, N. R. Sanchez, N.J. Ruiz, A.J. Escario, G.A. Barrio, R.A. Fernandez, and V. Aran, J. Med. Chem. 4, 78 (2009).

C. Cheptea, V. Sunel, L. Profire, M. Popa, and C. Lionte, Bul. Inst. Polit. Iasi 55, 85 (2009).

M.A. Hamilton, R.C. Russo, and R.V. Thurston, Envir. Sci. Techn. 12, 417 1978.

https://doi.org/10.1021/es60140a017

A. Azzouz, M. Leontie, D.O. Dorohoi, and C. Gheorghies, Elemente de Strategie in Design Industrial (Plumb, Bacau, 1998).

L. Fisher, Design for Environment, Creating Eco-Efficient Products and Processes (McGraw Hill, New York, 1996).

I. Hurjui, C. Cheptea, CF. Dascalu, L. Hurjui, C. Peptu, V. Sunel, and D.O. Dorohoi, Dig. J. Nanomater. Biostr. 7, 1747 (2012).

M. Moise, V. Sunel, M.M. Dulcescu, and D.O. Dorohoi, Rev. de Chim. 61, 799 (2010).

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Published

2018-10-19

How to Cite

Cheptea, C., Ivan, L. M., Dorohoi, D. O., Sunel, V., Hurjui, I., Saveanu, C. I., & Galaction, A. I. (2018). Optimized Synthesis and Spectral Characterization of Some Hydrazones Based on 5-Nitroindazole with Pharmacological Potential. Ukrainian Journal of Physics, 59(3), 313. https://doi.org/10.15407/ujpe59.03.0313

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Section

Solid matter