Sequential Ring-Closing Metathesis and Nitrone Cycloaddition on Glucose-Derived Substrates:  A Divergent Approach to Analogues of Spiroannulated Carbanucleosides and Conformationally Locked Nucleosides

Sahabuddin, Sk.; Roy, A. K.; Drew, Michael G. B.; Roy, Biswajit; Achari, Basudeb; Mandal, Sukhendu

doi:10.1021/jo0606554

Cited by 23 publications

(5 citation statements)

References 70 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A few reports in the literature deal with seven-membered polyhydroxylated ethers like septanosides (containing an anomeric center) [8] as well as compounds without an acetal moiety. Known methods for the construction of the seven-membered polyhydroxylated oxacycle, are for instance cycloaddition [9–11] or cyclodehydration of commercially available alcohols [12–14]. The disadvantages of these methods are the lack of selectivity as well as of stereocontrol and hence other routes are needed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Bouché¹,

Kandziora²,

Reißig³

2014

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryNew compounds with carbohydrate-similar structure (carbohydrate mimetics) are presented in this article. Starting from enantiopure nitrones and lithiated TMSE-allene we prepared three 1,2-oxazine derivatives which underwent a highly stereoselective Lewis acid-induced rearrangement to give bicyclic products in good yield. Subsequent reductive transformations delivered a library of new poly(hydroxy)aminooxepane derivatives. The crucial final palladium-catalyzed hydrogenolysis of the 1,2-oxazine moiety was optimized resulting in a reasonably efficient approach to a series of new seven-membered carbohydrate mimetics.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Bouché¹,

Kandziora²,

Reißig³

2014

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…19 Deprotection of 5′,6′-acetonide was selectively carried out using HClO 4 afforded triol 6 in 90% yield. 20 The conversion of diol to olefin 21 was achieved by reaction with imidazole, and PPh 3 in dry THF in the presence of iodine to give 7 in 68% yield (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

Antiproliferative activity of bicyclic benzimidazole nucleosides: synthesis, DNA-binding and cell cycle analysis

et al. 2016

View full text Add to dashboard Cite

An efficient route was developed for synthesis of bicyclic benzimidazole nucleosides from readily available d-glucose. The key reactions were Vörbruggen glycosylation and ring closing metathesis (RCM). Primarily, to understand the mode of DNA binding, we performed a molecular docking study and the binding was found to be in the minor groove region. Based on the proposed binding model, UV-visible and fluorescence spectroscopic techniques using calf thymus DNA (CT-DNA) demonstrated a non-intercalative mode of binding. Antiproliferative activity of nucleosides was tested against MCF-7 and MDA-MB-231 breast cancer cell lines and found to be active at low micromolar concentrations. Compounds and displayed significant antiproliferative activity as compared to and with the reference anticancer drug, doxorubicin. Cell cycle analysis showed that nucleoside induced cell cycle arrest at the S-phase. Confocal microscopy has been performed to validate the induction of cellular apoptosis. Based on these findings, such modified bicyclic benzimidazole nucleosides will make a significant contribution to the development of anticancer drugs.

show abstract

“…The Mandal group also used a similar strategy to synthesized spiroannulated carbapyrimidine nucleosides 668 , 674 , and 675 via ring-closing metathesis (RCM) and INC (Schemes 100 and 101). 100…”

Section: Miscellaneous Spirocyclic Nucleosidesmentioning

confidence: 99%

Advances in the Synthesis of Spirocyclic Nucleosides

Kumar,

Khan,

Arora

et al. 2023

Synthesis

View full text Add to dashboard Cite

The nucleosides are the building blocks for nucleic acids and composed of a five-carbon sugar bearing either pyrimidine or purine nucleobase. The biological properties of nucleosides can be tailored by chemically modifying the five-carbon sugar to influence its sugar pucker. The spirocyclic scaffold is an indispensable scaffold in more than ten approved drugs, and its inherent three-dimensionality makes it an ideal modification to influence the sugar pucker and biological properties of nucleosides. However, the introduction of spirocyclic scaffold is often synthetically challenging due to increase in synthetic steps and stereocenters. The present review highlights the advances in synthetic methodologies developed during the past decades for accessing various members of the spiro-functionalized nucleoside family.1 Introduction2 C-1′-Spirocyclic Nucleosides3 C-2′-Spirocyclic Nucleosides4 C-3′-Spirocyclic Nucleosides5 C-4′-Spirocyclic Nucleosides6 Miscellaneous Spirocyclic Nucleosides7 Conclusion and Future Perspectives

show abstract

Sequential Ring-Closing Metathesis and Nitrone Cycloaddition on Glucose-Derived Substrates: A Divergent Approach to Analogues of Spiroannulated Carbanucleosides and Conformationally Locked Nucleosides

Cited by 23 publications

References 70 publications

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Synthesis of new enantiopure poly(hydroxy)aminooxepanes as building blocks for multivalent carbohydrate mimetics

Antiproliferative activity of bicyclic benzimidazole nucleosides: synthesis, DNA-binding and cell cycle analysis

Advances in the Synthesis of Spirocyclic Nucleosides

Contact Info

Product

Resources

About