Recent Advances in Synthesis and Biological Activity of 4′‐Thionucleosides

Mulamoottil, Varughese A.; Majik, Mahesh S.; Chandra, Girish; Jeong, Lak Shin

doi:10.1002/9781118498088.ch14

Cited by 8 publications

(7 citation statements)

References 95 publications

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“…The 1 H NMR spectroscopic data were consistent with those reported in the literature. 27e In conclusion, the unprecedented DAST-mediated deoxygenative fluorination of benzoyl (24), TBDPS (25), and Bn (26, 29) protected 1-(-D-4-thioarabinofuranosyl)uracil at the sugar moiety was examined. Three kinds of products, the target thiolane Ns (30, 32, 34, 36), the ring-contracted thietane Ns (31, 33, 35, 37), and anhydro Ns (21,22,23) compounds were formed.…”

Section: Paper Synthesismentioning

confidence: 99%

“…1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 Among their sugar-modified analogues, 4′-thionucleosides, in which the oxygen atom in the furanose ring is replaced with a sulfur atom, have attracted much attention since the discovery of the antiviral and antitumor activities of 4′-thiothymidine ( 1 ) and 2′-deoxy-4′-thiocytidine ( 2 ) (Figure 1 ). 22 23 24 25 26…”

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confidence: 99%

“…Among their sugarmodified analogues, 4′-thionucleosides, in which the oxygen atom in the furanose ring is replaced with a sulfur atom, have attracted much attention since the discovery of the antiviral and antitumor activities of 4′-thiothymidine (1) and 2′-deoxy-4′-thiocytidine (2) (Figure 1). [22][23][24][25][26] The synthesis of 2′-substituted derivatives 3-6 of 2 and their evaluation for antineoplastic activity have been reported (Figure 2). 27 In the study, 4′-thioFAC 4 has emerged as a highly potent antineoplastic agent.…”

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confidence: 99%

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DAST-Mediated Fluorination of 1-[4-Thio-β-d-arabinofuranosyl]uracil: Investigation of Thiolane vs Thietane Formation and Stereoselective Synthesis of 4′-ThioFAC

Haraguchi¹,

Hannda²,

Wakasugi³

et al. 2022

Synthesis

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The unprecedented DAST-mediated (DAST = diethylaminosulfur trifluoride) deoxygenative fluorination of benzoyl-, TBDPS-, and Bn-protected 1-(β-d-4-thioarabinofuranosyl)uracil at the sugar portion was examined. Three kinds of nucleoside (Ns) products were formed: target thiolane Ns, ring-contracted thietane Ns, and anhydro Ns products. The reaction pathway was determined by the electronic effect of the protecting groups at the sugar and base moieties. The benzoylated uracil starting material gave the 2,2′-anhydronucleoside (anhydro Ns) as a major product, whereas the silylated and benzylated starting materials furnished the corresponding fluorinated products, in which the ring-contracted thietanes predominantly formed. The desired thiolane Ns could be obtained as major product by the addition of a pyridine derivative as an additive. Upon reacting N 3-benzoylated 1-(β-d-4-thioarabinofuranosyl)uracil with DAST in the presence of 2,4,6-collidine, the target 2′-deoxy-2′-β-fluoro-4′-thiouracil nucleoside could be obtained in 72% isolated yield along with the corresponding thietane Ns (7%) and anhydro Ns (3%) (thiolane Ns/thietane Ns/anhydro Ns = 10.3:1.00:0.43), with recovery of the starting material (12%). In this study, the first stereoselective synthesis of the β-anomer of 1-(2-deoxy-2-fluoro-4-thio-β-d-arabino-pentofuranosyl)cytosine (4′-thioFAC) has been developed.

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Section: Paper Synthesismentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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DAST-Mediated Fluorination of 1-[4-Thio-β-d-arabinofuranosyl]uracil: Investigation of Thiolane vs Thietane Formation and Stereoselective Synthesis of 4′-ThioFAC

Haraguchi¹,

Hannda²,

Wakasugi³

et al. 2022

Synthesis

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“…6 Three important sites are available for modifications viz ribose ring, the aromatic nucleoside base, and/or the phosphate group. Various ring sizes and different elements like N, S, Se, C [7][8][9][10][11][12] have been introduced in the central ribose component. Further, the positions of the above elements have also been changed.…”

Section: Introduction "Chemistry Without Catalysis Would Be a Sword W...mentioning

confidence: 99%

“…Various ring sizes and different elements like N, S, Se, C have been introduced on the central ribose component. [7][8][9][10][11][12] Further, the positions of the above elements have also been changed. All these modifications were pursued to obtain more therapeutically useful compounds.…”

Section: Introductionmentioning

confidence: 99%

Current Strategies on the Enantioselective Synthesis of Modified Nucleosides

Pal,

Chandra,

Mondal

et al. 2023

Synlett

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After the isolation of two carbocyclic nucleosides, viz Neplanocin A and Aristeromycin, from natural sources, a revolution came into the scientific community to develop more versatile, therapeutically useful compounds. For this purpose, many new methods for the synthesis of the carbocyclic framework of nucleosides have been developed. The consequences of this effort led to the successful development of many marketable drugs. Due to the inherent benefits such as higher lipophilicity and metabolic stability associated with carbocyclic nucleosides, like resistance against glycosidic hydrolysis and modification of aromatic bases by cellular phosphorylases, make them popular for the development of drugs against cancer and different viruses. Classically, carbocyclic nucleosides of various ring sizes and configurations have been synthesized starting from a chiral pool such as ribose and glucose, etc., but recently, many other new asymmetric versions have also been developed. Herein, we present a recent development in the catalytic enantioselective synthesis of nucleoside analogues, including carbocyclic and other varieties. This review provides new insights into the future development of modified nucleosides.

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Recent Advances in the Synthesis of Carbocyclic Nucleosides via Ring‐Closing Metathesis

2014

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The past decades witnessed the development and the strong potential of nucleoside analogues as therapeutic agents as well as biological tools. Among this, five‐membered carbocyclic nucleosides have shown immense promise in the treatment of cancer and viral infections. The systematic evolution of transition‐metal‐catalyzed CC bond‐forming reactions has widened the scope of olefin metathesis. The development of new catalysts, the selectivity, efficiency, functional‐group compatibility, along with a better know‐how of the catalyst–substrate interactions have encouraged researchers to use this powerful tool for the design of desired target compounds. The aim of this Focus Review is to highlight recently developed synthetic strategies for the synthesis of carbocyclic nucleosides involving ring‐closing metathesis (RCM) as a key step.

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Recent Advances in Synthesis and Biological Activity of 4′‐Thionucleosides

Cited by 8 publications

References 95 publications

DAST-Mediated Fluorination of 1-[4-Thio-β-d-arabinofuranosyl]uracil: Investigation of Thiolane vs Thietane Formation and Stereoselective Synthesis of 4′-ThioFAC

DAST-Mediated Fluorination of 1-[4-Thio-β-d-arabinofuranosyl]uracil: Investigation of Thiolane vs Thietane Formation and Stereoselective Synthesis of 4′-ThioFAC

Current Strategies on the Enantioselective Synthesis of Modified Nucleosides

Recent Advances in the Synthesis of Carbocyclic Nucleosides via Ring‐Closing Metathesis

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