Synthesis, physical-chemical and biological properties of 1.8-disubstituted of theobromine. V. 8-Benzylidenhydrazino-1-p-methylbenzyltheobromines

Authors

  • D. G. Ivanchenko Zaporizhzhia State Medical University,

DOI:

https://doi.org/10.14739/2310-1210.2015.5.53768

Keywords:

Xanthine, Organic Synthesis, NMR-spectroscopy, Acute Toxicity, Antioxidant Effect

Abstract

The problem of searching biologically active compounds amidst xanthine derivatives is a crucial one and is an issue for long-term investigation.

Aim. In order to find new biologically active compounds among xanthine derivatives, undescribed earlier 8-benzylidenhydrazino-1-p-methylbenzyltheobromines have been synthesized.

Methods and results. Reaction of 1-p-methylbenzyl-8-bromoxanthine with the excess of hydrazine hydrate in the aqueous dioxane is implemented through formation of 8-hydrazine-1(4-methylbenzyl)theobromine. Through the interaction of 8-hydrazinetheobromine with aldehydes in aqueous propan-2-ol respective 8-benzylidenhydrazino-1-p-methylbenzyltheobromines have been obtained. Structure of synthesized compounds has been definitely proved by NMR-spectroscopy.

Conclusions. Molecular and pharmacological descriptors of obtained substances have been calculated. The antioxidant activity of the obtained compounds has been explored. Priorities for further search of biologically active compounds in a range of xanthine derivatives have been set out. 

References

Dröge, W. (2002). Free radicals in the physiological control of cell function. Physiol. Rev., 82(1), 47–95.

Fridovich, I. (1978). The biology of oxygen radicals. Science, 201(4359), 875–880.

Steinbeck, M. J., Khan, A. U., & Karnovsky, M. J. (1993). Extracellular production of singlet oxygen by stimulated macrophages quantified using 9, 10-diphenylanthracene and perylene in a polystyrene film. J. Biol. Chem., 268(21), 15649–15654.

Kehrer, J. P. (2000). The Haber-Weiss reaction and mechanisms of toxicity. Toxicology, 149(1), 43–50. doi:10.1016/S0300-483X(00)00231-6.

Romanenko, M. I., Ivanchenko, D. H., Zhmurin, R. V., Yevsieieva, L. V., Shkoda, O. S., Myloserdova, H. V., et al. (2005). Syntez, fizyko-khimichni vlastyvosti ilidenpokhidnykh 8-hidrazyno-1-p-metylbenzylteobrominu [Synthesis, physical-chemical properties of iliden derivatives of 8-hydrazino-1-p-methylbenzyltheobromine]. Zaporozhskij medicinskij zhurnal, 6(33), 144–147. [in Ukrainian].

Ivanchenko, D. H., Romanenko, M. I., Samura, B. A., Taran, A. V., & Korniienko, V. I. (2012). Syntez, fizyko-khimichni ta biolohichni vlastyvosti pokhidnykh ksantynu. II. 1-p-khlorobenzyl-8-aminoteobrominy [Synthesis, physical-chemical and biological properties of xanthine derivatives. II. 1-p-chlorobenzyl-8-aminotheobromines]. Aktualni pytannia farmatsevtychnoi i medychnoi nauky ta praktyky, 2(8), 44–47. [in Ukrainian].

Ivanchenko, D. H., Romanenko, M. I., Kamyshnyi, O. M., & Polishchuk, N. M. (2014). Syntez, fizyko-khimichni ta biolohichni vlastyvosti 1,8-dyzamishchenykh teobrominu. III. 8-Amino-1-p-khlorobenzylteobrominy [Synthesis, physical-chemical and biological properties of 1,8-disubstituted of theobromine. III. 8-Amino-p-chlorobenzyltheobromines]. Aktualni pytannia farmatsevtychnoi i medychnoi nauky ta praktyky, 2(15), 45–49. [in Ukrainian].

Bielienichev, I. F., Hubskyi, Yu. I., Dunaiev, V. V., & Kovalenko, S. I. (2002) Metody otsinky antyoksydantnoi aktyvnosti rechovyn pry initsiiuvanni vilno-radykalnykh protsesiv u doslidakh in vitro [Methods for assessing antioxidant substances in initiating free radical processes in experiments in vitro]. Kyiv. [in Ukrainian].

Lipinski, Ch. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (2001). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Del. Rev., 46, 3–26. doi:10.1016/S0169-409X(00)00129-0.

Ghose, A. K., Viswanadhan, V. N., & Wendoloski, J. J. (1999). A Knowledge-Based Approach in Designing Combinatorial or Medicinal Chemistry Libraries for Drug Discovery. 1. A Qualitative and Quantitative Characterization of Known Drug Databases. J. Comb. Chem., 1, 55–68. doi: 10.1021/cc9800071.

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How to Cite

1.
Ivanchenko DG. Synthesis, physical-chemical and biological properties of 1.8-disubstituted of theobromine. V. 8-Benzylidenhydrazino-1-p-methylbenzyltheobromines. Zaporozhye Medical Journal [Internet]. 2015Nov.20 [cited 2024Jul.17];17(5). Available from: http://zmj.zsmu.edu.ua/article/view/53768

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Section

Problems of pharmacy