Nucleosides VI: The synthesis and optical properties of the 5′-(adenin-9-yl)-5′-deoxy derivatives of thymidine and 2′-deoxyadenosine

Fecher, Ronald; Boswell, Kay H.; Wittick, J. J.; Shen, T. Y.

doi:10.1016/s0008-6215(00)84900-9

Cited by 12 publications

(3 citation statements)

References 11 publications

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“…Shen and co-workers [ 57 – 58 ] proposed the synthesis of the double-headed nucleosides 5′-(adenine-9-yl)-5′-deoxythymidine ( 79 ) and 5′-(adenine-9-yl)-2′,5′-dideoxyadenosine ( 81 ) from 2′-deoxy-5′- O -tosylthymidine/adenosine 78 and 80 , respectively. The 2′-deoxy-5′- O -tosyl nucleosides were reacted with the sodium salt of adenine in DMF to afford the double-headed nucleosides 79 and 81 , respectively ( Scheme 18 ) [ 57 – 58 ].…”

Section: Reviewmentioning

confidence: 99%

Double-headed nucleosides: Synthesis and applications

Verma¹,

Maity²,

Maikhuri³

et al. 2021

Beilstein J. Org. Chem.

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Section: Reviewmentioning

confidence: 99%

Double-headed nucleosides: Synthesis and applications

Verma¹,

Maity²,

Maikhuri³

et al. 2021

Beilstein J. Org. Chem.

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“…The synthetic purine-nucleoside 9heade can also prepared as reported by T.Y. Shen et al [15]. Its purity was tested by elemental CHN-analysis, FT-IR spectroscopy, and thermogravimetric analysis (TGA).…”

Section: Reagentsmentioning

confidence: 99%

Novel Cd (II) Coordination Polymers Afforded with EDTA or Trans-1,2-Cdta Chelators and Imidazole, Adenine, or 9-(2-Hydroxyethyl) Adenine Coligands

et al. 2020

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Three mixed-ligands of Cd(II) coordination polymers were unintentionally obtained: {[Cd(µ3-EDTA)(Him)·Cd(Him)(H2O)2]·H2O}n (1), {[Cd(µ4-CDTA)(Hade)·Cd(Hade)2]}n (2), and {[Cd(µ3-EDTA)(H2O)·Cd(H9heade)(H2O)]·2H2O}n (3), having imidazole (Him), adenine (Hade) or 9-(2-hydroxyethyl)adenine (9heade) as the N-heterocyclic coligands. Compounds 2 and 3 were obtained by working with an excess of corresponding N-heterocyclic coligands. The single-crystal X-ray diffraction structures and thermogravimetric analyses are reported. The chelate moieties in all three compounds exhibit hepta-coordinated Cd centers, whereas the non-chelated Cd center is five-coordinated in 1 and six-coordinated in 2 and 3. Him and Hade take part in the seven-coordinated chelate moieties in 1 and 2, respectively. In contrast, 9heade is unable to replace the aqua ligand of the chelate [Cd (EDTA) (H2O)] moiety in 3. The thermogravimetric analysis (TGA) behavior of [Cd (H2EDTA) (H2O)]·2H2O in 1 and 3 leads to a residue of CdO, whereas the N-rich compound 2 yields CdO·Cd(NO3)2 as a residue. Density functional theory (DFT) calculations along with molecular electrostatic potential (MEP) and quantum theory of atoms-in-molecules computations were performed in adenine (compound 2) and (2-hydroxyethyl)adenine (compound 3) to analyze how the strength of the H-bonding and π-stacking interactions, respectively, are affected by their coordination to the Cd-metal center.

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“…An actualized search of “9-(2-hydroxyethyl) adenine” in SciFinder affords only 44 closely related references, comprising papers or patents. This literature concerns its own synthesis [ 16 , 17 ], its use to obtain adefovir dipivoxyl [ 18 ], and other issues. The synthesis of well-defined DNA mimics brush polymers bearing adenine moieties [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

Dicopper(II)-EDTA Chelate as a Bicephalic Receptor Model for a Synthetic Adenine Nucleoside

et al. 2021

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In the extensive field of metal ions, their interactions with nucleic acids, and their constituents, the main aim of this work is to develop a metal chelate suitable to recognize two molecules of an adenine nucleoside. For this purpose, the dinuclear chelate Cu2 (µ-EDTA) (ethylenediaminetetraacetate(4-) ion (EDTA)) is chosen as a bicephalic receptor model for N9-(2-hydroxyethyl)adenine (9heade). A one-pot synthesis is reported to obtain the compound [Cu2(µ2-EDTA)(9heade)2(H2O)4]·3H2O, which has been characterized by single-crystal X-ray diffraction and various spectral, thermal, and magnetic methods. The complex unit is a centro-symmetric molecule, where each Cu (II) center is chelated by a half-EDTA, and is further surrounded by an N7-dentate 9heade nucleoside and two non-equivalent trans-O-aqua molecules. The metal chelate-nucleoside molecular recognition is referred to as an efficient cooperation between the Cu-N7(9heade) coordination bond and a (9heade)N6-H···O(carboxyl, EDTA) interligand interaction. Theoretical calculations are also made to account for the relevance of this interaction. The extreme weakness with which each water molecule binds to the metal center disturbs the thermal stability and the infrared (FT-IR) and electron spin resonance (ESR) spectra of the compound.

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Nucleosides VI: The synthesis and optical properties of the 5′-(adenin-9-yl)-5′-deoxy derivatives of thymidine and 2′-deoxyadenosine

Cited by 12 publications

References 11 publications

Double-headed nucleosides: Synthesis and applications

Double-headed nucleosides: Synthesis and applications

Novel Cd (II) Coordination Polymers Afforded with EDTA or Trans-1,2-Cdta Chelators and Imidazole, Adenine, or 9-(2-Hydroxyethyl) Adenine Coligands

Dicopper(II)-EDTA Chelate as a Bicephalic Receptor Model for a Synthetic Adenine Nucleoside

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