The study of reactions of 7-substituted 8-hydrazino-3-methylxanthine with β-dicarbonyl compounds

Romanenko, N. I.; Назаренко, М. В.; Иванченко, Д. Г.; Pakhomova, O. O.; Sharapova, T. A.

doi:10.14739/2409-2932.2015.2.45125

Cited by 2 publications

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References 3 publications

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“…and high variability of chemical modification (6)(7)(8). At the same time, the hydrazine group is one of the most chemically active functional groups, which easily participates in reactions of nucleophilic addition (9,10) and insertion of such functional fragment to the structure of xanthine molecule could have some positive effect on its synthetic potential (9)(10)(11).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel ylidenhydrazides of 3-benzyl-8-methylxanthinyl-7-acetic acid as potential biological active compounds

Александрова

Левич

2017

Scripta Scientifica Pharmaceutica

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In this work, we have described the method of 3-benzyl-8-methylxanthinyl-7-acetohydrazide synthesis and studied its reaction with different aldehydes and ketones in acidic medium. As result, we obtained a series of novel ylidenhydrazides of 3-benzyl-8-methylxanthinyl-7-acetic acid. The structure of the synthesized substances was proved by IR and NMR spectra and elemental analysis and their individuality was confirmed by thin-layer chromatography.

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Section: Introductionmentioning

confidence: 99%

Synthesis of novel ylidenhydrazides of 3-benzyl-8-methylxanthinyl-7-acetic acid as potential biological active compounds

Александрова

Левич

2017

Scripta Scientifica Pharmaceutica

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“…One of the most chemically active functional groups is hydrazine group, which easily participate in reactions of nucleophilic addition [8,9]. Thus, insertion of such functional fragment in the structure of xanthine molecule could increase its synthetic potential [8][9][10].…”

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confidence: 99%

Synthesis and physical-chemical properties of 3-aryl-(aralkyl)-8-hydrazinemethylxanthines and their N-substituted derivatives

Александрова

Левич

Mikhalchenko

et al. 2016

Current Issues in Pharmacy and Medicine: Science and Practice

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Introduction. Analysis of last years' literature shows, that the most wide spread drugs are those, which contain in their structures heterocyclic fragment. Such trend could be explained by the fact that, heterocycle containing compounds are the part of the number of substances, which play an important role in the metabolic processes. It should be noted, that most of these drugs have unpleasant side effects and some of them are rather toxic. Xanthine derivatives are low toxic natural compounds with wide spectrum of pronounced pharmacological properties (antioxidant, diuretic, antibacterial, anti-infl ammatory etc.) and high variability of chemical modifi cation, that make these compounds handy objects for pharmaceutical research. Thus, synthesis of novel less toxic biologically active compounds-potential medicines-by chemical modifi cation of well-known natural substances, is one of the most important tasks of modern pharmaceutical science. Aim of our research was the development of method of 3-aryl(aralkyl)-8hydrazinemethylxanthines and their N-substituted derivatives synthesis and studying their physical-chemical properties. Materials and methods. Melting points were determined using capillary method on DMP (M). 1 Н NMR-spectra were recorded by Varian Mercury VX-200 device (company «Varian»-USA) solvent-(DMSO-d6), internal standard-ТМS. Elemental analysis of obtained compounds was produced on device Elementar Vario L cube. Results and discussion. We selected 3-aryl(aralkyl)-8-chloromethylxanthines as initial compounds for our study. By their interaction with hydrazine hydrate we obtained respective 8-hydrazinemethylxanthines. The next stage of our research was further chemical modifi cation of obtained 8-hydrazinemethylxanthines using the high ability of hydrazine residue for nucleophilic addition reactions. So, we studied the interaction of 3-aryl(aralkyl)-8-hydrazinemethylxanthines with phenylisothiocyanate and carbonyl compounds and synthesized number of N-substituted 8-hydrazinemethylxanthines. The structures of all obtained compounds were proved by the elemental analysis and 1 H NMR-spectroscopy. Conclusions. Obtained results of our work can be used for further search of biological active compounds among xanthine derivatives with hydrazine residue. Синтез і фізико-хімічні властивості 3-арил(аралкіл)-8-гідразинометилксантинів та їх N-заміщених похідних К. В. Александрова, С. В. Левіч, Є. К. Михальченко, Д. М. Сінченко Аналіз фахових літературних джерел останніх років показує, що найбільш поширеними лікарськими засобами є речовини, що містять у своїй структурі гетероциклічні фрагменти. Така тенденція може бути пов'язана з тим, що гетероциклічні сполуки відіграють важливу роль у метаболічних процесах. Слід відзначити, що більшість із цих препаратів мають неприємні побічні ефекти, а деякі з них є доволі токсичними. Похідні ксантину є природними гетероциклічними сполуками з малою токсичністю та широким спектром виражених фармакологічних властивостей (антиоксидантних, сечогінних, антибактеріальних, протизапальних...

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The study of reactions of 7-substituted 8-hydrazino-3-methylxanthine with β-dicarbonyl compounds

Cited by 2 publications

References 3 publications

Synthesis of novel ylidenhydrazides of 3-benzyl-8-methylxanthinyl-7-acetic acid as potential biological active compounds

Synthesis of novel ylidenhydrazides of 3-benzyl-8-methylxanthinyl-7-acetic acid as potential biological active compounds

Synthesis and physical-chemical properties of 3-aryl-(aralkyl)-8-hydrazinemethylxanthines and their N-substituted derivatives

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