A New Effective Method for the Synthesis of 1,2,4-Triazole-3-carboxamide and Ribavirin Derivatives

Chudinov, M. V.; Konstantinova, Irina D.; Ryzhova, O. I.; Есипов, Р. С.; Yurkevich, A. M.; Швец, В. И.; Мирошников, А. И.

doi:10.1007/s11094-005-0119-7

Cited by 15 publications

(8 citation statements)

References 14 publications

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“…In some applications, the enzymes were immobilized onto aminopropyl macroporous glass AP-CPG-170 and used for the synthesis of Virazole (48), ara-A (19) and 6-azauridine in 68, 56 and 45% isolated yields, respectively [99]. Recently, this study was extended to the synthesis of 5-substituted derivatives of Virazole [100].…”

Section: -Deaza-adementioning

confidence: 99%

“…An enzymatic synthesis of the broad spectrum antiviral nucleoside Virazole (48) catalyzed by nucleoside phosphorylases was frequently described (see, e.g., [ 74,99,100]). An attempt to employ similar enzymatic transglycosylation for the synthesis of its 2'-deoxyfluoro derivative, 1-(2-deoxy-2-fluoro--D-ribofuranosyl)-1,2,4-triazole -3-carboxamide (100), has, however, failed [121].…”

Section: N-deoxyribosyltransferases As Biocata-lystsmentioning

confidence: 99%

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Biotechnology of Nucleic Acid Constituents - State of the Art and Perspectives

Mikhailopulo

2007

COC

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A survey of the chemo-enzymatic methodology for the preparation of nucleosides of biological importance is presented. The emphasis is made on the enzymatic transglycosylation and glycosylation employing the nucleoside phosphorylases and N-deoxyribosyltransferases. Application of the whole cells as biocatalysts as well as purified enzymes from wild-type bacteria and recombinant enzymes is considered.

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Section: -Deaza-adementioning

confidence: 99%

Section: N-deoxyribosyltransferases As Biocata-lystsmentioning

confidence: 99%

Biotechnology of Nucleic Acid Constituents - State of the Art and Perspectives

Mikhailopulo

2007

COC

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“…For background, see: Chudinov et al (2005); Kamei et al (2005). Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

Pyridine-4-carboximidamidate chloride

Fan¹,

Wang²,

Zhang³

2009

Acta Cryst E

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In the title salt, C6H8N3 +·Cl−, each pyridinecarboximidamidate cation is linked to two symmetry-related cations through N—H⋯N hydrogen bonds, and to two chloride ions by N—H⋯Cl hydrogen bonds. The N—H⋯N hydrogen bonds involve the pyridine N atom and one NH2 group. In the crystal, N—H⋯N and N—H⋯Cl hydrogen bonds extend the structure into two-dimensional layers. Weak C—H⋯Cl interactions further connect these layers into a three-dimensional network.

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“…Because of its activity against both RNA and DNA viruses [8], it is recommended for the treatment of some infectious disorders including herpes [9], respiratory syncytial viral disease, and acute respiratory infections caused by adenovirus [10]. At present, ribavirin is also part of a combination therapy for the treatment of hepatitis C [11][12][13][14][15][16] and Lassa fever [14,15]. Furthermore, it has been evaluated for severe acute respiratory syndrome (SARS) and as an anti-cancer drug with successful results for the treatment of leukemia and breast cancer [16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Thermodynamic modelling of solubility and preferential solvation for ribavirin (II) in co-solvent mixtures of (methanol, n -propanol, acetonitrile or 1,4-dioxane) + water

Cong

et al. 2017

The Journal of Chemical Thermodynamics

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a b s t r a c tThe equilibrium solubility of ribavirin in solvent mixtures of {methanol (1) + water (2)}, {n-propanol (1) + water (2)}, {acetonitrile (1) + water (2)} and {1,4-dioxane (1) + water (2)} was determined experimentally by using isothermal dissolution equilibrium method within the temperature range from (278.15 to 318.15) K under atmospheric pressure (101.1 kPa). At the same temperature and mass fraction of methanol (n-propanol, acetonitrile or 1,4-dioxane), the mole fraction solubility of ribavirin is greater in (methanol + water) than in the other three solvent mixtures. The preferential solvation parameters were derived from their thermodynamic solution properties by means of the inverse Kirkwood-Buff integrals. The preferential solvation parameters for methanol, n-propanol, acetonitrile or 1,4-dioxane (dx 1,3 ) were negative in the four solvent mixtures with a very wide compositions, which indicated that ribavirin was preferentially solvated by water. Temperature had little effect on the preferential solvation magnitudes. The higher solvation by water could be explained in terms of the higher acidic behaviour of water interacting with the Lewis basic groups of the ribavirin. Besides, the solubility of the drugs was mathematically represented by using the Jouyban-Acree model, van't Hoff-Jouyban-Acree model and Apelblat-Jouyban-Acree model obtaining average relative deviations lower than 1.57% for correlative studies. It is noteworthy that the solubility data presented in this work contribute to expansion of the physicochemical information about the solubility of drugs in binary solvent mixtures and also allows the thermodynamic analysis of the respective dissolution and specific solvation process.

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A New Effective Method for the Synthesis of 1,2,4-Triazole-3-carboxamide and Ribavirin Derivatives

Abstract: A new method for the synthesis of 1,2,4-triazole-3-carboxamide and its 5-substituted analogs has been developed. The substrate specificity of purine nucleoside phosphorylase from E. coli with respect to the synthesized bases has been studied. 212 0091-150X/05/3904-0212

Cited by 15 publications

References 14 publications

Biotechnology of Nucleic Acid Constituents - State of the Art and Perspectives

Biotechnology of Nucleic Acid Constituents - State of the Art and Perspectives

Pyridine-4-carboximidamidate chloride

Thermodynamic modelling of solubility and preferential solvation for ribavirin (II) in co-solvent mixtures of (methanol, n -propanol, acetonitrile or 1,4-dioxane) + water

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