Synthesis, Transformations, and Physicochemical Properties of 3-(4′-Methylphenyl)-8-Methylxanthine Derivatives

Александрова, Е. В.; Левич, С. В.; Romanenko, N. I.; Шкода, А. С.; Mikhal′chenko, E. K.

doi:10.1007/s10600-014-0830-2

Cited by 2 publications

(3 citation statements)

References 11 publications

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“…Traube synthesis mechanism is the widely used industrial method for synthesis in which 5, 6-diaminouracils formed from urea or N-substituted urea and followed by cyclization i,e. ring closure [ 11 , 29 , 78 , 79 ]. Orthogonal safety-catch protection has been another strategy for synthesizing these derivatives [ 12 , 80 ].…”

Section: Main Textmentioning

confidence: 99%

Xanthine scaffold: scope and potential in drug development

Singh

Shreshtha

Thakur

et al. 2018

Heliyon

102

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Medicinal plants have been the basis for discovery of various important marketed drugs. Xanthine is one such lead molecule. Xanthines in various forms (caffeine, theophylline, theobromine, etc) are abode in tea, coffee, cocoa, chocolate etc. giving them popular recognition. These compounds are best known for their diverse pharmaceutical applications as cyclic nucleotide phosphodiesterase inhibition, antagonization of adenosine receptor, anti-inflammatory, anti-microbial, anti-oxidant and anti-tumor activities. These properties incentivize to use xanthine as scaffold to develop new derivatives. Chemical synthesis contributes greater diversity in xanthine based derivatisation. With highlighting the existing challenges in chemical synthesis, the present review focuses the probable solution to fill existing lacuna. The review summarizes the available knowledge of xanthine based drugs development along with exploring new xanthine led chemical synthesis path for bringing diversification in xanthine based research. The main objective of this review is to explore the immense potential of xanthine as scaffold in drug development.

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Section: Main Textmentioning

confidence: 99%

Xanthine scaffold: scope and potential in drug development

Singh

Shreshtha

Thakur

et al. 2018

Heliyon

102

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“…3-Benzyl-8-propylxanthinyl-7-acetic acid, its amide and propyl ester were synthesized using xanthine alkylation methodic [11]. Reaction was carried out in DMF in the presence of calculated amount of NaHCO 3 and addition chloroacetic acid, chloroacetamide or propyl chloroacetate as reagents (Fig.…”

Section: Results and Their Discussionmentioning

confidence: 99%

“…Полученные в ходе нашей работы результаты могут быть использованы для дальнейшего поиска биологически активных соединений среди карбоксилсодержащих ксантинов. Ammonium salts of 3-benzyl-8-propylxanthinyl-7-acetic acid (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15). Method A.…”

Section: Methodsunclassified

Synthesis and physical-chemical properties of 3-benzyl-8-propylxanthinyl-7-acetic acid and its derivatives

Mikhal′chenko¹,

Александрова²,

Левич³

et al. 2017

Current Issues in Pharmacy and Medicine: Science and Practice

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Introduction. Heterocyclic compounds play an important role in the metabolic processes of human organism. Structures of vitamins, nucleotides, chromoproteins are based on Nitrogen-containing heterocycles (purine, pyrimidine, thiazole etc). Thus, it was obvious to use these organic substances as basic molecules for synthetic research of biologically active compounds which could be used for treatment of different pathological processes. In their research, some scientist pay special attention to xanthine derivatives that are well-known low toxic natural compounds with wide spectrum of pronounced pharmacological properties (antioxidant, diuretic, antibacterial, anti-inflammatory etc). Insertion of carboxyl group in the structure of xanthine molecule is a prospective ability of its synthetic potential increasing. Aim of our research was the development of method of 3-benzyl-8-propylxanthinyl-7-acetic acid and its 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-benzyl-8-propyl xanthine as initial compound for our study. By its interaction with chloroacetic acid, chloroacetamide or propyl chloroacetate in DMF in the presence of calculated amount of NaHCO 3 we synthesized 3-benzyl-8propylxanthinyl-7-acetic acid its ester and amide. At the same time we found that obtaining of xanthinyl-7-acetic acid by hydrolysis of its ester produced with higher yield. On the next stage of our research we synthesized a number of water-soluble salts of 3-benzyl-8propylxanthinyl-7-acetic acid by reaction of acid with different primary and secondary amines. 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 biologically active compounds among xanthine derivatives with carboxyl residue.

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Synthesis, Transformations, and Physicochemical Properties of 3-(4′-Methylphenyl)-8-Methylxanthine Derivatives

Cited by 2 publications

References 11 publications

Xanthine scaffold: scope and potential in drug development

Xanthine scaffold: scope and potential in drug development

Synthesis and physical-chemical properties of 3-benzyl-8-propylxanthinyl-7-acetic acid and its derivatives

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