Synthesis of morpholine nucleoside triphosphates

Abramova, Tatyana V.; Bakharev, Pavel A.; Vasilyeva, Svetlana V.; Silnikov, Vladimir N.

doi:10.1016/j.tetlet.2004.03.193

Cited by 28 publications

(22 citation statements)

References 7 publications

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“…1 13 A pale greenish-yellow crystalline solid (yield 91 %) was isolated by flash column chromatography on silica gel (MeOH/CH 2 Cl 2 2-3 %), m.p.…”

Section: Morpholino-modified 7ј-o-tbdps-n-trityl-5-(n-dansyl-1-aminopmentioning

confidence: 99%

“…1 13 Aza-Michael Addition Product 10a: Acrylonitrile (160 μL, 2.4 mmol), KOAc (74 mg, 0.75 mmol), and nBu 4 NBr (106 mg, 0.33 mmol) were added under Ar to a stirred solution of 3 (250 mg, 0.3 mmol) in dry DMF (2.5 mL). The resulting mixture was stirred and heated at 90°C for 5 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in CHCl 3 (50 mL).…”

Section: Heck Coupling Of Morpholino-modified 7ј-o-tbdps-n-trityl-5iomentioning

confidence: 99%

“…The organic phase was washed with water and brine and dried with anhydrous Na 2 SO 4 . 1 13 1 13 Aza-Michael Addition Product 10a: Acrylonitrile (160 μL, 2.4 mmol), KOAc (74 mg, 0.75 mmol), and nBu 4 NBr (106 mg, 0.33 mmol) were added under Ar to a stirred solution of 3 (250 mg, 0.3 mmol) in dry DMF (2.5 mL).…”

Section: Heck Coupling Of Morpholino-modified 7ј-o-tbdps-n-trityl-5iomentioning

confidence: 99%

“…The resulting mixture was heated at 90°C for 11-14 h (depending on the boronic acid, Table 7). 13 The organic phase was washed with water and brine and dried with anhydrous Na 2 SO 4 .…”

Section: General Procedures For Suzuki Coupling Of Morpholino-modifiedmentioning

confidence: 99%

“…1 150.6, 150.4, 135.64, 135.62, 133.3, 133.2, 131.8, 129.9, 129.86, www.eurjoc.org 13 Supporting Information (see footnote on the first page of this article): 1 H and 13 C NMR spectra of all new compounds and crystallographic data for 6, 7j, 10a, and 20. 1 150.6, 150.4, 135.64, 135.62, 133.3, 133.2, 131.8, 129.9, 129.86, www.eurjoc.org 13 Supporting Information (see footnote on the first page of this article): 1 H and 13 C NMR spectra of all new compounds and crystallographic data for 6, 7j, 10a, and 20.…”

Section: General Procedures For Suzuki Coupling Of Morpholino-modifiedmentioning

confidence: 99%

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Synthesis of Nucleobase‐Functionalized Morpholino‐Modified Nucleoside Monomers Through Palladium‐Catalyzed Cross‐Coupling Reactions

Nandi¹,

Pattanayak²,

Paul³

et al. 2013

Eur J Org Chem

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Morpholino‐modified nucleoside analogues have widespread applications in developmental biology. To achieve nucleobase‐functionalized forms of morpholino nucleosides, syntheses of 5‐substituted cytidine, 8‐substituted adenosine, and 8‐substituted guanosine morpholino nucleoside monomers are described for the first time. The syntheses are based on the use of 5‐iodocytidine, 8‐bromoadenosine, and 8‐bromoguanosine morpholino nucleosides as the key starting materials. These iodo or bromo derivatives have also been synthesized for the first time. Palladium‐mediated cross‐coupling reactions (Sonogashira, Suzuki, and Heck) were then employed with the halo derivatives to accomplish the substitutions. Different reaction conditions for C, A, and G were standardized to achieve the conversions. The strategy was devised in such a way that the useful N‐trityl protecting groups remain at the end. The catalyst combinations used for Sonogashira, Suzuki, and Heck reactions were Pd(PPh3)2Cl2·CuI, Pd(dppf)Cl2·CH2Cl2, and Pd(OAc)2, respectively. Heck coupling between 5‐iodocytidine monomer and methyl acrylate worked well, whereas with acrylonitrile the exocyclic amine of cytidine was found to form the aza‐Michael adduct. In this context, treatment of iodocytidine with methyl acrylate under two different sets of conditions was found to produce either the Michael addition product or the Heck coupling product. Four of the functionalized morpholino monomers have been further confirmed by single‐crystal X‐ray structural analysis. All of these functionalized monomers were obtained in good to excellent overall yields.

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“…1 13 A pale greenish-yellow crystalline solid (yield 91 %) was isolated by flash column chromatography on silica gel (MeOH/CH 2 Cl 2 2-3 %), m.p.…”

Section: Morpholino-modified 7ј-o-tbdps-n-trityl-5-(n-dansyl-1-aminopmentioning

confidence: 99%

Section: Heck Coupling Of Morpholino-modified 7ј-o-tbdps-n-trityl-5iomentioning

confidence: 99%

Section: Heck Coupling Of Morpholino-modified 7ј-o-tbdps-n-trityl-5iomentioning

confidence: 99%

“…The resulting mixture was heated at 90°C for 11-14 h (depending on the boronic acid, Table 7). 13 The organic phase was washed with water and brine and dried with anhydrous Na 2 SO 4 .…”

Section: General Procedures For Suzuki Coupling Of Morpholino-modifiedmentioning

confidence: 99%

Section: General Procedures For Suzuki Coupling Of Morpholino-modifiedmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of Nucleobase‐Functionalized Morpholino‐Modified Nucleoside Monomers Through Palladium‐Catalyzed Cross‐Coupling Reactions

Nandi¹,

Pattanayak²,

Paul³

et al. 2013

Eur J Org Chem

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Novel Pyrimidine‐based Ferrocenyl substituted Organometallic Compounds: Synthesis, Characterization and Biological Evaluation

Parveen

Alsharif

Alahmdi

et al. 2018

Applied Organom Chemis

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Some novel pyrimidine-based ferrocenyl substituted organometallic compounds were synthesized via multistep reactions, well characterized by different spectroscopic techniques and elemental analyses and evaluated for in vitro antiprotozoal susceptibility against HM1: IMSS strain of Entamoeba histolytica. The results of antiprotozoal susceptibility unveiled these compounds, as new leads in protozoal chemotherapy as most of the organometallics displayed an exceptionally higher antiamoebic activity (IC 50 = 0.055 μM -0.815 μM) than the reference drug metronidazole which gave IC 50 (50% inhibitory concentration) value 1.781 μM in our experiments, concluding that newly synthesized organometallic compounds have potential to be employed as effective antiamoebic agents and these organometallics can be very useful for further optimization work on amoebic chemotherapy. KEYWORDSantiprotozoal assay, ferrocenyl unit, HM1: IMSS strain of Entamoeba histolytica, new leads in amoebic chemotherapy, novel pyrimidine-based organometallics

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How To Form a Phosphate Anhydride Linkage in Nucleotide Derivatives

Sherstyuk

Abramova

2015

ChemBioChem

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The fundamental roles of nucleoside triphosphates and nucleotide cofactors such as NAD(+) in biochemistry are well known. In recent decades, continuing research has revealed the key role of 5'-capped RNA and 5',5'-dinucleoside polyphosphates in the regulation of vitally important physiological processes. Last but not least, the commercial potential of nucleoside triphosphate synthesis can hardly be overestimated. Nevertheless, despite decades of investigation and the obvious topicality of the research on the chemical synthesis of the nucleotide compounds containing phosphate anhydride linkages, none of the existing procedures can be considered an up-to-date "gold standard". However, there are a number of fruitful synthetic approaches to forming phosphate anhydride linkages in satisfactory yield. These are summarized in this concise review, organized by the type of active phosphorous intermediate and reagents used.

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Synthesis of morpholine nucleoside triphosphates

Cited by 28 publications

References 7 publications

Synthesis of Nucleobase‐Functionalized Morpholino‐Modified Nucleoside Monomers Through Palladium‐Catalyzed Cross‐Coupling Reactions

Synthesis of Nucleobase‐Functionalized Morpholino‐Modified Nucleoside Monomers Through Palladium‐Catalyzed Cross‐Coupling Reactions

Novel Pyrimidine‐based Ferrocenyl substituted Organometallic Compounds: Synthesis, Characterization and Biological Evaluation

How To Form a Phosphate Anhydride Linkage in Nucleotide Derivatives

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