Synthesis, stereochemistry, intramolecular cyclization, and rates of hydrolysis of adenosine 2′,3′-acetals

Bakthavachalam, Venkatesalu; Lin, Lee-Gin; Cherian, X. M.; Czarnik, Anthony W.

doi:10.1016/0008-6215(87)85011-5

Cited by 18 publications

(21 citation statements)

References 13 publications

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“…14 Antiviral Activity. The phosphoramidates (18)(19)(20)(21)(22)(23) were characterized in Vitro as inhibitors of HCV replication in the HCV replicon assay using similar conditions as described. 8 Data are presented in Table 2 as EC 50 values representing the concentration of compound reducing HCV replication by 50% and CC 50 values representing the concentration of compound reducing cell viability by 50% as determined using the WST assay.…”

Section: Resultsmentioning

confidence: 99%

First Example of Phosphoramidate Approach Applied to a 4‘-Substituted Purine Nucleoside (4‘-Azidoadenosine): Conversion of an Inactive Nucleoside to a Submicromolar Compound versus Hepatitis C Virus

et al. 2007

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We report on the synthesis of the anti hepatitis C virus (HCV) agent 4'-azidoadenosine (1) and the application of the phosphoramidate ProTide technology to this nucleoside. The synthesis of 1 was achieved through an epoxide intermediate followed by regio- and stereoselective ring opening by azidotrimethylsilane in the presence of a Lewis acid. Compound 1 did not inhibit HCV replication in cell culture at concentrations up to 0.1 mM. However, a submicromolar active agent could be derived from 1 by the application of the ProTide technology. All the phosphoramidates prepared were L-alanine derivatives with variations in the aryl moiety and in the ester part of the amino acid. The benzyl ester and the l-naphthyl phosphate (18) had the best activity in replicon assay. Phosphoramidates (18-21) achieved a significant improvement in antiviral potency over the parent nucleoside (1) with no increase in cytotoxicity.

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Section: Resultsmentioning

confidence: 99%

First Example of Phosphoramidate Approach Applied to a 4‘-Substituted Purine Nucleoside (4‘-Azidoadenosine): Conversion of an Inactive Nucleoside to a Submicromolar Compound versus Hepatitis C Virus

et al. 2007

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“…Most importantly, compound 1 and catalyst (PTSA) were stable, solid and easy to use at room temperature. Earlier compound 1 was used for the synthesis of p-nitrophenyl b-D-ribofuranoside derivatives, which were used as substrate analogues for nucleoside glycosylase enzymes [26,27]. Another derivative of compound 1 i.e.…”

Section: Resultsmentioning

confidence: 99%

“…The compound 1 was synthesized from commercially available inexpensive materials [26] in 78% yield. Most importantly, compound 1 and catalyst (PTSA) were stable, solid and easy to use at room temperature.…”

Section: Resultsmentioning

confidence: 99%

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A Novel Method for Monitoring the Transesterification Reaction of Oil in Biodiesel Production by Estimation of Glycerol

Reddy

Devamani

Chadha

2010

J Americ Oil Chem Soc

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A quantitative method is reported for the estimation of glycerol during transesterification of oil to form biodiesel. The reagent used to derivatize glycerol was 9,9-dimethoxyfluorene. Glycerol is estimated by both UV-visible spectrophotometric and high performance liquid chromatography methods. Using the former method, detection limits of 0.05% w/w of glycerol in biodiesel was established. Validation of the developed method was done using the Greenhill method for determination of free glycerol formed during the transesterification reaction.

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“…Compound 3 was immediately converted to benzylidene 4 via transacetylation to prevent reversion back to compound 2 . The acetal forming reaction produced a mixture of diastereomers due to non-selective formation of the acetal carbon 7 . Compound 4 was hydrolyzed to the carboxylic acid 5 with 48 % overall yield in four steps.…”

Section: Resultsmentioning

confidence: 99%

Efficient microwave-assisted solid phase coupling of nucleosides, small library generation, and mild conditions for release of nucleoside derivatives

Paritala

Suzuki

Carroll

2013

Tetrahedron Letters

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Nucleosides are essential bio-molecules that participate in a wide array of biological processes involved in maintaining physiologic homeostasis. Recent efforts geared towards the synthesis of nucleoside analogues and development of nucleoside combinatorial libraries using solid phase synthesis has contributed invaluable information towards drug design and development. These studies have provided information concerning the structural requirements of substrate binding pockets of enzymes and evaluation of enzyme kinetics. However, the synthesis of nucleosides and its corresponding analogues remains a challenging and time consuming process. Herein, we report an efficient, microwave assisted solid phase coupling of nucleosides, combinatorial chemistry on the coupled nucleosides to generate small library and mild cleavage conditions to release nucleoside derivatives from its solid support. We anticipate these findings will accelerate the development of synthetic methods or combinatorial library design of nucleoside analogues in similar settings.

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Synthesis, stereochemistry, intramolecular cyclization, and rates of hydrolysis of adenosine 2′,3′-acetals

Cited by 18 publications

References 13 publications

First Example of Phosphoramidate Approach Applied to a 4‘-Substituted Purine Nucleoside (4‘-Azidoadenosine): Conversion of an Inactive Nucleoside to a Submicromolar Compound versus Hepatitis C Virus

First Example of Phosphoramidate Approach Applied to a 4‘-Substituted Purine Nucleoside (4‘-Azidoadenosine): Conversion of an Inactive Nucleoside to a Submicromolar Compound versus Hepatitis C Virus

A Novel Method for Monitoring the Transesterification Reaction of Oil in Biodiesel Production by Estimation of Glycerol

Efficient microwave-assisted solid phase coupling of nucleosides, small library generation, and mild conditions for release of nucleoside derivatives

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