7-Deazapurine (Pyrrolo[2,3-d]pyrimidine) 2-Deoxyribonucleosides: Syntheses and Transformations

  title={7-Deazapurine (Pyrrolo[2,3-d]pyrimidine) 2-Deoxyribonucleosides: Syntheses and Transformations},
  author={F. Seela and S. Budow and Xiaohua Peng},
  journal={Current Organic Chemistry},
Abstract: This review reports on the synthesis of 7-deazapurine (pyrrolo[2,3-d]pyrimidine) 2’-deoxyribonucleosides, including -Dand -L-enantiomers, fluoro derivatives, and 2’,3’-dideoxyribonucleosides. It covers the various aspects of convergent nucleoside synthesis. Stereochemically defined -D and -L 2’-deoxyribonucleosides as well as sugar derivatives were prepared by nucleobase anion glycosylation. This glycosylation reaction is regioselective for the pyrrole nitrogen and stereoselective for… Expand
19 Citations

Tables from this paper

Synthesis of 8-(1,2,3-triazol-1-yl)-7-deazapurine nucleosides by azide-alkyne click reactions and direct C-H bond functionalization.
Treatment of toyocamycin or sangivamycin with 1,3-dibromo-5,5-dimethylhydantoin in MeOH (r.t./30 min) gave 8-bromotoyOCamycin and 8- bromosangivamcin in good yields and a large Stokes shifts of ~ 100 nm. Expand
Synthesis of solvatofluorochromic 7-arylethynylated 7-deaza-2′-deoxyadenosine derivatives: application to the design of environmentally sensitive fluorescent probes forming stable DNA duplexes
Abstract We synthesized environmentally sensitive fluorescent (ESF) 7-deaza-2′-deoxyadenosine derivatives including ethynylanthracene substituted atzA (1) and ethynylnaphthalene substituted nzA (2a),Expand
7-Deaza-2'-deoxyguanosine: Selective Nucleobase Halogenation, Positional Impact of Space-Occupying Substituents, and Stability of DNA with Parallel and Antiparallel Strand Orientation.
CD spectra indicate that functionalization leads only to local distortion of the double helix while the overall structure of aps and ps DNA is maintained, and surprisingly, the bulky phenyltriazolyl "click" residue is well-accommodated at the 7-position of ps DNA and even led to a stabilization of the parallel doubleHelix. Expand
Gemcitabine, Pyrrologemcitabine, and 2'-Fluoro-2'-Deoxycytidines: Synthesis, Physical Properties, and Impact of Sugar Fluorination on Silver Ion Mediated Base Pairing.
The addition of silver ions to DNA duplexes with a fluorine-modified "dC-dC" pair near the central position led to significant duplex stabilization, and the increase in stability was higher for duplexs with fluorinated sugar residues than for those with an unchanged 2'-deoxyribose moiety. Expand
Facile protection-free one-pot synthesis of 7-deaza-2=-deoxyguanosine-5=-triphosphate — A versatile molecular biology probe
A simple, straightforward, reliable, and efficient protection-free “one-pot, three-step” chemical synthesis of 7-deaza-2′-deoxyguanosine-5′-triphosphate (7-deaza-dGTP) is described. The reactionExpand
5-Aza-7-deaza-2'-deoxyguanosine and 2'-Deoxycytidine Form Programmable Silver-Mediated Base Pairs with Metal Ions in the Core of the DNA Double Helix.
The dZ-Ag+ -dC base pair is slightly less stable than the dG-dC pair, shows sequence dependence, and consumes one or two silver ions, which make it suitable for programmable incorporation of silver ions in DNA which cannot be achieved by canonical base pairs. Expand
Imidazolo-dC metal-mediated base pairs: purine nucleosides capture two Ag(+) ions and form a duplex with the stability of a covalent DNA cross-link.
Owing to the ease of nucleobase deprotonation, the new Ag(+) -mediated base pair containing a "purine" skeleton is much stronger than that derived from the pyrrolo- [3,4-d]pyrimidine system ((ph) PyrdC, 1). Expand
Synthesis of Purine and 7‐Deazapurine Nucleoside Analogues of 6‐N‐(4‐Nitrobenzyl)adenosine; Inhibition of Nucleoside Transport and Proliferation of Cancer Cells
The design and synthesis of novel tool compounds for the further study of hENT1 are reported here and type‐specific inhibition of cancer cell proliferation was observed at micromolar concentrations with the 4‐N‐(4‐nitrobenzyl) derivatives of sangivamycin and toyocamycin antibiotics. Expand
Silver Ions in Non-canonical DNA Base Pairs: Metal-Mediated Mismatch Stabilization of 2'-Deoxyadenosine and 7-Deazapurine Derivatives with 2'-Deoxycytidine and 2'-Deoxyguanosine.
The stability increase of canonical DNA mismatches might have an impact on cellular DNA repair and the specific binding of silver ions was confirmed by stoichiometric UV titration experiments, which proved that one silver ion is captured by one mismatch. Expand
Silver-Mediated Base Pairs in DNA Incorporating Purines, 7-Deazapurines, and 8-Aza-7-deazapurines: Impact of Reduced Nucleobase Binding Sites and an Altered Glycosylation Position.
Stable silver-mediated "dA-dC" base pair mismatches were detected for all nucleosides and when the equivalents of silver ions were increased to the number of total base pairs every base pair consumed one silver ion. Expand


Synthesis of 6-substituted 7-carbapurine 2',3'-dideoxynucleosides: solid-liquid phase-transfer glycosylation of 4-chloropyrrolo[2,3-d]pyrimidine and deoxygenation of its 2'-deoxyribofuranoside
Several 4-substituted pyrrolo[2,3-d]pyrimidine 2′, 3′-dideoxyribofuranosides including 2′,3′-dideoxytubercidin (10) and 2′,3′-dideoxy-7-carbainosine (12) are prepared fromExpand
Total synthesis of 2'-deoxytoyocamycin, 2'-deoxysangivamycin and related 7-β-D-arabinofuranosylpyrrolo[2,3-d]pyrimidines via ring closure of pyrrole precursors prepared by the stereospecific sodium salt glycosylation procedure
Abstract A stereospecific high-yield glycosylation of a fully aromatic pyrrole, 2-bromo-(or ethylthio)-5-ethoxymethyleneamino-pyrrole-3, 4-dicarbonitrile( 14a and 14b ) has been accomplished for theExpand
Pyrrolo[2,3- d ]pyrimidine β-L-Nucleosides Containing 7-Deazaadenine, 2-Amino-7-deazaadenine, 7-Deazaguanine, 7-Deazaisoguanine, and 7-Deazaxanthine
The synthesis and properties of 7-deazapurine β-L-nucleosides are described. The stereoselective glycosylation of the anions of 2-amino-6-chloro-7-deazapurines 9a, 9b or 6-chloro-7-deazapurines 13a,Expand
A facile and improved synthesis of tubercidin and certain related pyrrolo[2,3‐d]pyrimidine nucleosides by the stereospecific sodium salt glycosylation procedure
A simple synthesis of tubercidin (1), 7-deazaguanosine (2) and 2′-deoxy-7-deazaguanosine (14) has been accomplished using the sodium salt glycosylation procedure. Reaction of the sodium salt ofExpand
Synthesis and biological evaluation of 6-(alkyn-1-yl)furo[2,3-d]pyrimidin-2(3H)-one base and nucleoside derivatives.
Derivatives of the 2'-deoxynucleoside of furo[2,3-d]pyrimidin-2(3H)-one with long-chain alkyl (or 4-alkylphenyl) substituents at C6 exhibit remarkable anti-VZV (varicella-zoster virus) potency andExpand
7-Functionalized 7-deazapurine ribonucleosides related to 2-aminoadenosine, guanosine, and xanthosine: glycosylation of pyrrolo[2,3-d]pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose.
Conformational analysis of selected nucleosides on the basis of proton coupling constants and using the program PSEUROT showed that these ribonucleosides exist in a preferred S conformation in solution. Expand
Synthesis and biological activity of certain 6-substituted and 2,6-disubstituted 2'-deoxytubercidins prepared via the stereospecific sodium salt glycosylation procedure.
A number of 6-substituted and 2,6-disubstituting pyrrolo[2,3-d]pyrimidine 2'-deoxyribonucleosides were prepared by the direct stereospecific sodium salt glycosylation procedure and showed significant activity against measles in vitro. Expand
Abstract A general and stereospecific method has been developed for the direct preparation of βD-ribofuranosyl, βD-arabinofuranosyl and 2-deoxy-βD-erythro-pentofuranosyl derivatives of a number ofExpand
Synthesis and antiproliferative and antiviral activity of 2'-deoxy-2'-fluoroarabinofuranosyl analogs of the nucleoside antibiotics toyocamycin and sangivamycin.
Even though compound 10 was cytotoxic, which will probably preclude its use as an antiviral drug, the difference between cytotoxicity and activity against HCMV, HIV, and VZV was sufficient to indicate specific activity against a viral target. Expand
1,N6-Etheno-2′-deoxytubercidin and pyrrolo-C: synthesis, base pairing, and fluorescence properties of 7-deazapurine nucleosides and oligonucleotides
Abstract The synthesis of 1,N6-etheno-7-deaza-2′-deoxyadenosine (12b) which was prepared from 7-deaza-2′-deoxyadenosine (5a) with chloroacetaldehyde is described. Also the regioselectiveExpand