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How does Europe PMC derive its citations network? Protein Interactions. Protein Families. Nucleotide Sequences. Functional Genomics Experiments. Protein Structures. Gene Ontology GO Terms. Data Citations. They were reported synthesis of novel racemic conformationally locked nucleosides with bicyclo[2. Two methodologies were employed for introduction of the chloropurine moiety to the scaffold: i the Mitsunobu reaction of the chloropurine nucleobase with appropriate alcohols and ii a built-up strategy from appropriate amines. These compounds could be considered as the 6-chloropurines substituted at position 9 with different substituted bicyclic scaffolds bicyclo[2.

These bicyclo systems norbornene or norbornane , like the oxabicyclo[2. All compounds were evaluated for antiviral activity against Coxsackie virus B3, as shown in Table 1. Most analogues showed activity in the low micromolar range with minimal cytotoxicity to the cell line used in this study.

Studies on the mode of action of the most promising compounds are in progress. Quadrelli and coworkers synthesized the isoxazoline-based carbocyclic nucleosides and by the linear construction of the desired purine and pyrimidine bases on the regioisomeric aminols Scheme 1. The complex course of 1,3-dipolar cycloaddition between benzonitrile oxide and the cyclohexadiene adduct of nitrosocarbonyl benzene afford regioisomeric mixtures of exo and endo cycloadducts. The exo cycloadducts of are suitable starting materials for isoxazoline-cyclohexane nucleoside synthesis.

Detachment of the benzoyl group and reductive cleavage of the N—O bond provided the stereodefined aminols , which were used for the linear construction of purine nucleosides by well-established synthetic protocols. Substitution with 5-amino-4,6-dichloropyrimidine and subsequent condensation with orthoformates afford the chloropurines and []. These were further derivatized by replacement of the chlorine with amines and alkoxides to give suitable samples for antiviral tests in very good yields.

The same group was synthesized isoxazoline-carbocyclic nucleosides hav- ing a hydroxymethylene side chain, and a variety of analogues was attained starting from the stereodefined heterocyclic aminol , which are readily avail- able through exo selective 1,3-dipolar cycloadditions of benzonitrile oxide to 2-azanorbornenes and elaboration of the cycloadducts Scheme 1.

The stereodefined heterocyclic aminols afford the carbocyclic skeleton for the linear construction of the purine rings. Functionalization of the chloropurines — [] with a variety of amines extended the synthetic potential of this strategy, allowing for a fine-tuning of their biological and antiviral activity as well as comparison with the corresponding nor-nucleosides. Biological evaluation of the newly obtained compounds — is in progress.

The first ones have the base moiety directly attached to the ring, whereas the other ones have a spacer between the base and the ring Figure 1. Chu and coworkers accomplished the first asymmetric synthesis of d- and l-cyclopropyl nucleosides, which belong to the first category Scheme 1. The requisite cyclopropyl ring was installed by Simmons-Smith cyclopropanation following oxidation, Curtius rearrangement and deprotection protocol to yield cyclopropyl amine The target d-nucleosides were obtained by a linear methodology.

Unfortunately, no significant biological activity was exhibited by synthesized nucleosides. On the other hand, in the second category, several biologically interesting nucleosides were discovered. Ashton et al. Tsuji and coworkers explored extensive SAR of carbocyclic nucleosides bearing a methylene spacer between the base and car- bocyclic ring [,]. Furthermore, this nucleoside was 8- to fold more potent than acyclovir and penciclovir against VZV, and the selectivity index of nucleoside was also high.

As an extension of the research, a series of 5-substituted uracil derivatives were prepared, and some of the target nucleosides exhibited potent anti-VZV activity Scheme 1. Particularly, 5-bromovinyl nucleoside was about fold more potent than acyclovir and had good oral bioavailability in rats The enantiomeric syntheses of compounds and were accomplished using chiral cyclo- propane lactone as starting material.

Zemlicka and coworkers described another type of interesting carbocyclic nucleosides, in which the spacer between the base and the ring is an unsatu- rated double bond [,]. Compounds, such as and Figure 1. The pair of enantiomers and was synthesized through enzymatic as well as chemical resolutions Schemes 1. Further modifications of the spacer generated spiropentane nucleoside Scheme 1. R -Methylenecyclopropylcarbinol was converted in few steps to reagents , which were used for alkylation-elimination of adenine and Scheme 1.

Nucleosides, Nucleotides and Oligonucleotides Conference GRC

It is not cytotoxic, and its efficacy is somewhat lower than that of ganciclovir. Preparation of carbocyclic analogs of the natural counterparts was first reported by Honjo []. In addition, the d-enantiomer of C -OXT-G , lobucavir, LBV could be phosphorylated to its triphosphate by viral TK as well as protein kinase [] and exhibited broad-spectrum antiviral activity against HBV and herpes viruses [].

However, the clinical studies were suspended due to oncogenicity in rodents. Further modifications based on the structure of C -OXTs generated series of interesting four-membered carbocyclic nucleosides. Novel spiro-carbocyclic nucleosides and have been prepared by Chu and coworkers via enzymatic resolution Scheme 1. Reagents and conditions: a P. The NMR conformational studies suggested that the nucleosides antiviral activity was correlated with their predominant conformation Figure 1.

Virus input was 20 plaque-forming units PFU. The values are means of two independent determinations. It is well known that opposite enantiomers can display dif- ferent pharmacological and toxicological properties. Hence, Alibs and coworkers report an enantiodivergent approach to d- and lhydroxycyclohexenyl nucleo- sides — [], starting from the common intermediate , which bears a hydrobenzoin moiety as the chiral auxiliary Schemes 1.

They Scheme 1. Unfortunately, none of the compounds was found anti-HIV active. Particularly, the discovery of aba- cavir and entecavir as clinically effective antiviral agents prompted the studies of various carbocyclic nucleosides. Although the synthesis of carbocyclic nucle- osides has advanced dramatically, more efficient and practical methods are still in demand for the preparation of biologically active compounds as well as chi- ral key intermediates. In the future, novel biologically interesting carbocyclic nucleosides will likely be continuously discovered to improve the existing list of chemotherapeutic agents.

Adams, R. De Clercq, E. Antiviral drugs in current clinical use. Journal of Clinical Virology, 30 , — Galmarini, C. Nucleoside analogues and nucle- obases in cancer treatment. The Lancet Oncology, 3 , — Stoeckler, J. Human erythrocytic purine nucleoside phosphorylase: Reaction with sugar-modified nucleoside substrates. Biochemistry, 19 , — Shealy, Y. Journal of the American Chemical Society, 88 , — Hayashi, M. Nucleic Acids Symposium Series, vol. Kusaka, T. Streptomyces citricolor nov.

And a new antibiotic, aristeromycin. Journal of Antibiotics, 21 , — Agrofoglio, L. Synthesis of carbocyclic nucleosides. Tetrahedron, 50 , — Crimmins, M. New developments in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides. Tetrahedron, 54 , — Jeong, L. Recent advances in the synthesis of the carbocyclic nucleosides as potential antiviral agents. Schneller, S. Carbocyclic nucleosides carbanucleosides as new therapeutic leads. Current Topics in Medicinal Chemistry, 2 , — Zhu, X. The latest progress in the synthesis of carbocyclic nucleosides.

Nucleosides, Nucleotides and Nucleic Acids, 19 , — Marquez, V. Carbocyclic nucleosides. Medicinal Research Reviews, 6 , 1— Borchardt, R. Neplanocin A. A potent inhibitor of S -adenosylhomocysteine hydrolase and of vaccinia virus multiplication in mouse l cells. Journal of Biological Chemistry, , S -aristeromycinyl-L-homocysteine, a potent inhibitor of S -adenosylmethionine-dependent transmethylations.

Journal of Medicinal Chem- istry, 19 , — Coward, J. Analogs of S -adenosylhomocysteine as potential inhibitors of biological transmethylation. Specificity of the S -adenosylhomocysteine binding site. Journal of Medicinal Chemistry, 16 , — Analogs of S -adenosylhomocysteine as poten- tial inhibitors of biological transmethylation. Synthesis and biological activity of homocysteine derivatives bridged to adenine.

Journal of Medicinal Chemistry, 15 , — S -adenosylhomocysteine hydrolase inhibitors as broad- spectrum antiviral agents.

1. Introduction

Biochemical Pharmacology, 36 , — Guranowski, A. Adenosine analogs as substrates and inhibitors of S -adenosylhomocysteine hydrolase. Biochemistry, 20 , — Palmer, J. The mechanism of action of S -adenosyl- homocysteinase. Parry, R. Studies of enzyme stereochemistry. Elucidation of the stereochemistry of the reaction catalyzed by S -adenosylhomocysteine hydrolase. Journal of the American Chemical Society, , — Sinhababu, A.

Mechanism of action of S -adenosyl-L-homocysteine hydrolase. Abeles, R. Bio- chemistry, 21 , — Matuszewska, B. The role of nicotinamide adenine dinu- cleotide in the inhibition of bovine liver S -adenosylhomocysteine hydrolase by neplanocin a. Journal of Biological Chemistry, , — Wolfson, G. Neplanocin a. Actions on S -adenosylhomocysteine hydrolase and on hormone synthesis by gh4c1 cells. Design, synthe- sis, and biological evaluation of fluoroneplanocin a as the novel mechanism-based inhibitor of S -adenosylhomocysteine hydrolase.

Journal of Medicinal Chemistry, 46 , — Wnuk, S. Journal of Medicinal Chemistry, 41 , — Nucleic acid-related compounds. Journal of Medicinal Chemistry, 37 , — Yang, X.

Reward Yourself

Biochemistry, 39 , — Yuan, C. Nucleosides, Nucleotides and Nucleic Acids, 24 , — Madhavan, G. The Journal of Organic Chemistry, 51 , — Cermak, R. Carbocyclic ribofuranosylamine for the synthesis of carbocyclic nucleosides. Tetrahedron Letters, 22 , — Maggini, M.

Biomolecules - Nucleotides and Nucleosides

Tetrahedron Letters, 31 , — Palmer, C. Synthesis of carbocyclic clitocine. Synthesis of carbocyclic analogs of purine ribonucleosides. Journal of the American Chemical Society, 91 , — Trost, B. Transition-metal-controlled synthesis of. An unusual directive effect in hydroxylations. Arita, M. Enantioselective syn- thesis of the carbocyclic nucleosides — -aristeromycin and — -neplanocin a by a chemicoenzymatic approach. Arai, Y. Dimethyl R S isobornylsulfinyl maleate, a chiral synthetic equivalent of dimethyl acetylenedicarboxylate: Preparation and its application to the formal chiral synthesis of — -neplanocin a and — -aristeromycin.

Tetrahedron Letters, 29 , — An enanti- oconvergent route to carbocyclic nucleosides — -aristeromycin and — -neplanocin a via the asymmetric Diels—Alder reaction. Journal of the Chemical Society, Perkin Transactions 1 , , — Boyer, S. Carbocyclic nucleoside analogs. Concise enan- tioselective synthesis of functionalized cyclopentanes and formal total synthesis of aristeromycin. The Journal of Organic Chemistry, 62 , — Brown, B. A novel, one-pot ring expansion of cyclobu- tanones.

Syntheses of carbovir and aristeromycin. The Journal of Organic Chemistry, 65 , — Deardorff, D. Conversion of allylic alcohols into allylic nitromethyl compounds via a palladium-catalyzed solvolysis: An enantioselective synthesis of an advanced carbocyclic nucleoside precursor. The Journal of Organic Chemistry, 61 , — Palladium-catalyzed enantioselective synthesis of carbanucleosides. Asymmetric alkylation of nitroalkanes Ange- wandte Chemie, 39 , — Borcherding, D. Synthesis of analogs of neplanocin A: Utilization of optically active dihydroxycyclopentenones derived from carbohydrates.

The Journal of Organic Chemistry, 52 , — Wolfe, M. Tetrahedron Letters, 30 , — Jin, Y. Efficient and practical synthesis of d-cyclopent enone, the key intermediate for the synthesis of carbocyclic nucleosides. Tetrahedron Letters, 43 , — Practical synthesis of D- and Lcyclopentenone and their utility for the synthesis of car- bocyclic antiviral nucleosides against orthopox viruses smallpox, monkeypox, and cowpox virus.

The Journal of Organic Chemistry, 68 , — Wang, P. Asymmet- ric synthesis of L-cyclopentyl carbocyclic nucleosides. Tetrahedron Letters, 38 , — Chiral synthesis of carbocyclic analogues of L-ribofuranosides. The Journal of Organic Chemistry, 64 , — Yang, M. Preparation of carbocyclic S - adenosylazamethionine accompanied by a practical synthesis of — -aristeromycin. The Journal of Organic Chemistry, 69 , — Total synthesis of — -neplanocin A. The Journal of Organic Chemistry, 53 , — Camps, P.

Tetra- hedron, 38 , — Medich, J.

Recent Advances in Nucleosides: Chemistry and Chemotherapy

Synthesis of the carbocyclic nucleoside — -neplanocin A. Tetrahedron Letters, 28 , — Song, G. Journal of Medicinal Chemistry, 44 , — Michel, B. Synthesis of — -neplanocin A with the highest overall yield via an efficient mitsunobu coupling. Tetrahedron, 63 , — Bennett Jr. Metabolic studies with carbocyclic analogs of purine nucleosides. Molecular Pharmacology, 4 , — Glazer, R. A cyclopentenyl analog of adenosine with specificity for inhibiting RNA methylation.

Biochemical Pharmacology, 35 , — Keller, B. Purification and characteriza- tion of some metabolic effects of S-neplanocylmethionine. Molecular Pharmacol- ogy, 28 , — Li, W. Ando, T. Synthesis of 2-modified aristeromycins and their analogs as potent inhibitors against Plasmodium falciparum S -adenosyl-L-homocysteine hydrolase. Kitade, Y.

Patil, S. Journal of Medicinal Chemistry, 35 , — Siddiqi, S. Journal of Medicinal Chemistry, 48 , — Yin, X. Ault-Riche, D. Molecular Pharmacology, 43 , — Hasobe, M. Das, S. Rajappan, V. Roy, A. Tetrahedron, 61 , — Seley-Radtke, K. Carbocyclic thymidine analogs for use as potential therapeutic agents. Carroll, S. Inhibition of hepatitis C virus RNA replication by 2-modified nucleoside analogs. Eldrup, A.

Journal of Medicinal Chemistry, 47 , — Ko, O. Journal of Medicinal Chemistry, 31 , — Tetrahedron Letters, 46 , — Chiang, P. S -adenosyl-L-homocysteine hydro- lase: Analogues of S -adenosyl-L-homocysteine as potential inhibitors. Molecular Pharmacology, 13 , — Broad-spectrum antiviral activity of the carbocyclic analog of 3-deazaadenosine. Antiviral Research, 3 , 17— Journal of Medicinal Chemistry, 38 , — Lin, W. Syntheses of new spirocarbocyclic nucleoside analogs using iminonitroso diels-alder reactions. Organic Letters, 11 , — Diastereoselective synthesis of a spiro-noraristeromycin using an acyl-nitroso Diels- Alder reaction.

Journal of Organic Chemistry, 74 , — Kojima, H. Sadler, J. Synthetic strategies toward carbocyclic purine-pyrimidine hybrid nucleosides. Li, H. Rao, J. Kim, Y. Structure-activity relationships of carbocyclic 6-benzylthioinosine analogues as subversive substrates of Toxoplasma gondii adenosine kinase. Obara, T. New neplanocin analogues. Synthesis and antiviral activ- ity of 2-halo derivatives of neplanocin A.

Journal of Medicinal Chemistry, 39 , — Shuto, S. IV: 2-fluoroneplanocin A: An adenosine deaminase-resistant equivalent of neplanocin A. Chemical and Pharmaceutical Bulletin, 42 , — Andrei, G. Inhibitory effect of selected antiviral compounds on arenavirus replication in vitro. Antiviral Research, 14 , — Shigeta, S. Antimicrobial Agents and Chemotherapy, 36 , — New neplanocin analogs. Journal of Medicinal Chemistry, 45 , — Antimicrobial Agents and Chemotherapy, 31 , — Ye, W.

Tetrahedron Letters, 50 , — Park, A. Nucleic Acids Symposium Series, 52 , — Bulletin of the Korean Chemical Society, 29 , — Lee, H. Bulletin of the Korean Chemical Society, 30 , — Radi, M. A convergent approach for the synthesis of ara-neplanocin A analogs under sub-zero microwave assisted conditions. Chu, C. Antiviral activity of cyclopentenyl nucleosides against orthopox viruses smallpox, monkeypox and cow- pox. Park, Y. Truncated fluorocyclopentenyl pyrimidines as S -adenosylhomocysteine hydrolase inhibitors.

Asymmetric synthesis of novel apio carbocyclic nucleoside analogues as potential antiviral and antitumor agent. Asymmetric synthesis of apio fluoroneplanocin a analogs as potential adohcy hydrolase inhibitor. Enantioselective synthesis and antivi- ral activity of purine and pyrimidine cyclopentenyl C-nucleosides. Cho, J. Syn- thesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and sars. Journal of Medicinal Chemistry, 49 , — Arumugham, B. Synthe- sis and antiviral activity of 7-deazaneplanocin A against orthopoxviruses vaccinia and cowpox virus.

Kim, H. Synthesis and anti-hepatitis B virus and anti-hepatitis C virus activities of 7-deazaneplanocin A analogues in vitro. Journal of Medicinal Chemistry, 52 , — Bodenteich, M. Ellis, M. Antimicrobial Agents and Chemotherapy 33 3 Furman, P. Fyfe, J. Glazier, A. The metabolism and antiviral activity of a novel group of anti herpes prodrugs. Paper No. Uribandai, Fukushima, Japan, May 23, The metabolism and antiviral activity of a novel group of anti-herpes prodrugs.

Gomez almaguer, D. Gomez-almaguer, D. Hoard, D. Hunt, B. Chemistry and Industry Hutchinson, D. The synthesis, reaction and properties of nucleoside mono , di , tri , and tetraphosphates and nucleotides with changes in the phosphoryl residue. In Chemistry of Nucleotides and Nucleosides, L. Townsend, ed. The synthesis, reaction and properties of nucleoside mono-, di-, tri-, and tetraphosphates and nucleotides with changes in the phosphoryl residue.

King History, pharmacokinetics, and pharmacology of acyclovir. Krenitsky, T. The Journal of Biological Chemistry 6 Lobe, D. Antiviral Research Masch et al.


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