Synthesis and Biological Activity of Amino Acid Esters of Acyclovir

Stankova, Ivanka; Dzimbova, Tatyana; Shishkov, Stoyan

doi:10.1007/978-0-387-73657-0_77

Cited by 4 publications

(6 citation statements)

References 8 publications

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“…The low stability of amino acid esters in water solutions does not allow a drug being developed to be administered as an injection. Therefore, ACV esters with the aminomethylbenzoyl group have been analyzed to prove that the incorporation of an aromatic ring between the amino group and the carboxyl group stabilizes the molecule , whereas the insertion of a thiazole ring does not have such an effect . For the purpose of use after oral and nasal mucosa administration, the stability of aliphatic (ACV) esters ( n ‐butyrate, pivalate, valerate, and hexanoate) has been investigated.…”

Section: Introductionmentioning

confidence: 99%

Comparative Analysis of Acyclovir Esters Stability in Solutions: The Influence of the Substituent Structure, Kinetics, and Steric Effects

Lesniewska

Gola

Dutkiewicz

et al. 2015

Int J of Chemical Kinetics

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Reversed‐phase high‐performance liquid chromatography has been applied to the determination of acyclovir (ACV) esters such as acetate, isobutyrate, pivalate, ethoxycarbonate, and nicotinate. All analyses were carried out at laboratory temperature using a column LiChrospher RP‐18 (250 × 4 mm, 5 µm) and a proper mobile phase consisting of acetonitrile and phosphate buffer (pH 6 or 6.7) or acetonitrile and potassium dihydrogen phosphate, and acetic acid. The methods were validated by the determination of the following parameters: selectivity, precision, accuracy, and linearity. Kinetic studies on the hydrolysis were investigated in solutions at 310 K over the pH range 0.42–1.38. The pH‐profiles indicated specific acid‐catalyzed and spontaneous water‐catalyzed degradation. The stability of the studied ACV esters were determined not only by steric factors. In the case of ethoxycarbonyl ester of ACV, the hydrolysis was a two‐step reaction.

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Section: Introductionmentioning

confidence: 99%

Comparative Analysis of Acyclovir Esters Stability in Solutions: The Influence of the Substituent Structure, Kinetics, and Steric Effects

Lesniewska

Gola

Dutkiewicz

et al. 2015

Int J of Chemical Kinetics

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“…Acyclovir derivatives modified with amino acids and peptides [15][16][17][18] and acyclovir containing peptidomimetics [19,20] have been reported but acyclovir containing cinnamic acids are not known. In order to obtain analogues with more desirable characteristics, we synthesized new esters of acyclovir containing p-coumaric, ferulic, and sinapic acids.…”

Section: Chemistrymentioning

confidence: 99%

Cinnamic Esters of Acyclovir-Synthesis and Biological Activity

Stankova

Chuchkov

Wutzler

et al. 2010

Nucleosides, Nucleotides and Nucleic Acids

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In the present study we have synthesized esters of acyclovir with cinnamic acids (p-coumaric, ferulic, and sinapic acids) and evaluated them for their antiviral and antioxidant potential. The antiviral activity of the newly synthesized compounds has been tested against human herpes virus 1 (HSV-1) in vitro. The results indicate that none of the synthesized compounds inhibits the tested virus strain. The antioxidant properties have been studied using 2,2-diphenyl-1-picrylhydrazyl (DPPH)* test.

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“…The only exception with prominent activity against HSV-2 turned out to be the Ala-thiazolyl ester of acyclovir [8, 9]. The object of this study was to assess the chemical stability of some of the synthesised acyclovir esters with peptidomimetics at pH 1.0 and pH 7.4 at 37°C.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, we synthesised acyclovir esters with peptidomimetics and studied their antiviral activity against HSV-1 and HSV-2 [ 8 – 10 ].…”

Section: Introductionmentioning

confidence: 99%

“…Contrary to acyclovir esters with natural amino acids, the results showed that modification of acyclovir with thiazole, oxazole and thiazolyl-thiazole containing amino acids (Gly, Val, Ala, Leu) decreased the antiviral effect of acyclovir. The only exception with prominent activity against HSV-2 turned out to be the Ala-thiazolyl ester of acyclovir [ 8 , 9 ]. The object of this study was to assess the chemical stability of some of the synthesised acyclovir esters with peptidomimetics at pH 1.0 and pH 7.4 at 37°C.…”

Section: Introductionmentioning

confidence: 99%

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Chemical Stability of New Acyclovir Analogues with Peptidomimetics

Hristov

Stankova²

2011

Sci. Pharm.

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In the search for new and effective prodrugs against the herpes simplex virus, a series of acyclovir analogues with a thiazole ring containing amino acids (glycine, alanine, valine, leucine) has been investigated. The chemical stability of some of the compounds containing different residues was studied at pH 1 and pH 7.4 at a temperature of 37°C. An HPLC method was developed for quantification of the unchanged ester concentration.Some of the esters (Gly-thiazole, Ala-thiazole-acyclovir, Leu-thiazole-acyclovir) were rather unstable, especially under acidic conditions, and underwent rapid hydrolysis into the chemical precursor acyclovir. At pH 7.4, the stability of Valthiazole-acyclovir was remarkable. At this pH, Val-thiazole-acyclovir showed stability higher than that of valacyclovir (the first effective prodrug of acyclovir).

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Synthesis and Biological Activity of Amino Acid Esters of Acyclovir

Cited by 4 publications

References 8 publications

Comparative Analysis of Acyclovir Esters Stability in Solutions: The Influence of the Substituent Structure, Kinetics, and Steric Effects

Comparative Analysis of Acyclovir Esters Stability in Solutions: The Influence of the Substituent Structure, Kinetics, and Steric Effects

Cinnamic Esters of Acyclovir-Synthesis and Biological Activity

Chemical Stability of New Acyclovir Analogues with Peptidomimetics

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