Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides

Kartik Temburnikar and Katherine L. Seley-Radtke
Beilstein J. Org. Chem. 2018, 14, 772–785. https://doi.org/10.3762/bjoc.14.65

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Recent advances in synthetic approaches for medicinal chemistry of C-nucleosides
Kartik Temburnikar and Katherine L. Seley-Radtke
Beilstein J. Org. Chem. 2018, 14, 772–785. https://doi.org/10.3762/bjoc.14.65

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Temburnikar, K.; Seley-Radtke, K. L. Beilstein J. Org. Chem. 2018, 14, 772–785. doi:10.3762/bjoc.14.65

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  • Pfeiffer, M.; Nidetzky, B. C-Ribosylating Enzymes in the (Bio)Synthesis of C-Nucleosides and C-Glycosylated Natural Products. ACS Catalysis 2023, 13, 15910–15938. doi:10.1021/acscatal.3c04436
  • Sung, K.; Aswar, V. R.; Song, J.; Jarhad, D. B.; Jeong, L. S. Stereoselective Approach for the Synthesis of Diverse 1'-Modified Carbanucleosides. Organic letters 2023, 25, 8377–8381. doi:10.1021/acs.orglett.3c03518
  • Penjarla, S.; Reddy, P. Y.; Penta, S.; Sanghvi, Y. S.; Eyer, L.; Štefánik, M.; Růžek, D.; Banerjee, S. Efficient synthesis of novel 2-deoxy-C-nucleosides containing oxa and thiadiazole derivatives and their biological activity. Journal of Molecular Structure 2023, 1292, 136099. doi:10.1016/j.molstruc.2023.136099
  • Abd Al Moaty, M. N.; El Kilany, Y.; Awad, L. F.; Ibrahim, N. A.; Abu-Serie, M. M.; El-Yazbi, A.; Teleb, M. Discovery of novel benzimidazole acyclic C-nucleoside DNA intercalators halting breast cancer growth. Archiv der Pharmazie 2023, 357, e2300454. doi:10.1002/ardp.202300454
  • Ojeda-Porras, A. C.; Roy, V.; Bourzikat, O.; Favetta, P.; Agrofoglio, L. A. Cobalt-assisted route to rare carbocyclic C-ribonucleosides. RSC advances 2023, 13, 30777–30786. doi:10.1039/d3ra04937j
  • Mukhin, E. M.; Savateev, K. V.; Voinkov, E. K.; Ulomsky, E. N.; Rusinov, V. L. 3-Halopyrazolo[1,5-a]pyrimidines as promising precursors of novel C-nucleosides. Russian Chemical Bulletin 2023, 72, 1821–1836. doi:10.1007/s11172-023-3965-0
  • Maria, C.; Rauter, A. P. Nucleoside analogues: N-glycosylation methodologies, synthesis of antiviral and antitumor drugs and potential against drug-resistant bacteria and Alzheimer's disease. Carbohydrate research 2023, 532, 108889. doi:10.1016/j.carres.2023.108889
  • Dörrenhaus, R.; Wagner, P. K.; Kath-Schorr, S. Two are not enough: synthetic strategies and applications of unnatural base pairs. Biological chemistry 2023, 404, 883–896. doi:10.1515/hsz-2023-0169
  • Pfeiffer, M.; Ribar, A.; Nidetzky, B. A selective and atom-economic rearrangement of uridine by cascade biocatalysis for production of pseudouridine. Nature communications 2023, 14, 2261. doi:10.1038/s41467-023-37942-7
  • Mukhin, E. M.; Savateev, K. V.; Rusinov, V. L. Approaches to the synthesis of heterocyclic C-nucleosides. Russian chemical bulletin = Izvestiia Akademii nauk. Seriia khimicheskaia 2023, 72, 425–481. doi:10.1007/s11172-023-3810-1
  • Majima, R.; Edwards, T. C.; Dreis, C. D.; Geraghty, R. J.; Bonnac, L. F. Enhanced Remdesivir Analogues to Target SARS-CoV-2. Molecules (Basel, Switzerland) 2023, 28, 2616. doi:10.3390/molecules28062616
  • Li, W.; Girt, G. C.; Radadiya, A.; Stewart, J. J. P.; Richards, N. G. J.; Naismith, J. H. Experimental and computational snapshots of C-C bond formation in a C-nucleoside synthase. Open biology 2023, 13, 220287. doi:10.1098/rsob.220287
  • Pfeiffer, M.; Nidetzky, B. Biocatalytic cascade transformations for the synthesis of C-nucleosides and N-nucleoside analogs. Current opinion in biotechnology 2023, 79, 102873. doi:10.1016/j.copbio.2022.102873
  • Kurahayashi, K.; Hanaya, K.; Sugai, T.; Hirai, G.; Higashibayashi, S. Copper-Catalyzed Stereoselective Borylation and Palladium-Catalyzed Stereospecific Cross-Coupling to Give Aryl C-Glycosides. Chemistry (Weinheim an der Bergstrasse, Germany) 2022, 29, e202203376. doi:10.1002/chem.202203376
  • Poudel, T. N.; Panda, S.; Orimoloye, M.; Hegde, P.; Aldrich, C. C. 1'-Cyano Intermediate Enables Rapid and Stereoretentive Access to 1'-Modified Remdesivir Nucleosides. The Journal of organic chemistry 2022, 87, 14452–14462. doi:10.1021/acs.joc.2c01897
  • Rosenqvist, P.; Mäkinen, J. J.; Palmu, K.; Jokinen, J.; Prajapati, R. K.; Korhonen, H. J.; Virta, P.; Belogurov, G. A.; Metsä-Ketelä, M. The role of the maleimide ring system on the structure-activity relationship of showdomycin. European journal of medicinal chemistry 2022, 237, 114342. doi:10.1016/j.ejmech.2022.114342
  • Roy, V.; Agrofoglio, L. A. Nucleosides and emerging viruses: A new story. Drug discovery today 2022, 27, 1945–1953. doi:10.1016/j.drudis.2022.02.013
  • Wang, Q.; Sun, Q.; Jiang, Y.; Zhang, H.; Yu, L.; Tian, C.; Chen, G.; Koh, M. J. Iron-catalysed reductive cross-coupling of glycosyl radicals for the stereoselective synthesis of C-glycosides. Nature Synthesis 2022, 1, 235–244. doi:10.1038/s44160-022-00024-5
  • Matyugina, E. S.; Kochetkov, S. N.; Khandazhinskaya, A. L. Synthesis and biological activity of aza and deaza analogues of purine nucleosides. Russian Chemical Reviews 2021, 90, 1454–1491. doi:10.1070/rcr5013

Patents

  • HERDEWIJN PIET; GROAZ ELISABETTA; QINGFENG LI. NOVEL 6-SUBSTITUTED 7-DEAZAPURINES AND CORRESPONDING NUCLEOSIDES AS MEDICAMENTS. WO 2021164848 A1, Aug 26, 2021.
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