4016-63-1

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Chemical Properties

White Solid

InChI:InChI=1/C10H12BrN5O5/c11-9-13-3-6(14-10(12)15-7(3)20)16(9)8-5(19)4(18)2(1-17)21-8/h2-5,8,17-19H,1H2,(H2,12,15,20)/t2-,3?,4?,5?,8-/m1/s1

Upstream product

• 15717-45-0 2',3',5'.-tri-O-acetyl-8-bromoguanosine 
• 118-00-3 G 

Downstream Products

• 26001-38-7 8-mercaptoguanosine 
• 118-00-3 G 
• 168701-80-2 8-nitroguanine 
• 80106-09-8 8-nitroxanthine 
• 79953-03-0 8-phenylguanosine 
• 79953-04-1 2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-p-tolyl-1,9-dihydro-purin-6-one 
• 557-40-4 Allyl ether 
• 126138-81-6 8-(allyloxy)-2-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one 
• 21082-30-4 9-β-(D-ribofuranosyl)-1H-purine-2,6,8(3H,7H,9H)-trione 
• 3868-37-9 8-benzyloxy-xanthosine 
• 54898-41-8 8-(hydroxymethyl)guanosine 
• 1350627-73-4 2-amino-9-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-(4-methoxystyryl)-1H-purin-6(9H)-one 
• 1350627-74-5 2-amino-9-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-(4-(trifluoromethyl)styryl)-1H-purin-6(9H)-one 

Relevant academic research and scientific papers

Self-Assembly of Functionalized Lipophilic Guanosines into Cation-Free Stacked Guanine-Quartets

The hierarchical self-assembly of various lipophilic guanosines exposing either a phenyl or a ferrocenyl group in the C(8) position was investigated. In a solution, all the derivatives were found to self-assemble primarily into isolated guanine (G)-quartets. In spite of the apparent similar bulkiness of the two substituents, most of the derivatives form disordered structures in the solid state, whereas a specific 8-phenyl derivative self-assembles into an unprecedented, cation-free stacked G-quartet architecture.

Self-Assembly of a Guanosine Derivative To Form Nanostructures and Transmembrane Channels

We herein report the self-assembly of a lipophilic bromoguanosine derivative (G1) in homogeneous solution, in the solid state and in planar bilayer membranes. The self-assembly of G1, driven by H-bonding and π–π stacking interactions can form different nano-structures depending on incubation time. The G1 nanostructure is able to bind a bioactive dye like Rose Bengal. In crystal state, it shows ribbon type H-bonding pattern and exhibits birefringence in polarized light. And further, the self-assembled nanostructure of G1 can form discrete transmembrane ion channels in lipid bilayer membranes, enabling passage of potassium ions.

Synthesis and in vitro evaluation of antiviral and cytostatic properties of novel 8-triazolyl acyclovir derivatives

As a part of the research aimed on identification of new nucleobase derivatives with improved biological properties, a series of novel 8-substituted acyclovir derivatives were synthesized. The 8-azidoguanosine 4 and novel 8-azidoacyclovir 9 were synthesized from commercially available guanosine 1 and acyclovir 6 which were transformed into 8-bromopurine derivatives 2 and 7 and hydrazine derivatives 3 and 8, respectively. 8-Triazolylguanosine 5 and 8-triazolylacyclovir analogs 10–12 were successfully synthesized via the Cu(I) catalyzed 1,3-dipolar cycloaddition reaction of azides 4 and 9 with propargyl alcohol, 4-pentyn-1-ol and 5-hexyn-1-ol. The novel 1,4-disubstituted 1,2,3-triazolyl compounds 5, 10–12 were evaluated for antiviral activity against selected DNA and RNA viruses and cytostatic activity against normal Madine Darby canine kidney (MDCK I) cells, and seven tumor cell lines (HeLa, CaCo-2, NCI-H358, Jurkat, K562, Raji and HuT78). While tested compounds exerted no antiviral activity at nontoxic concentrations, the 8-triazolyl acyclovir derivative 10, with the shortest alkyl substituent at the C-4 of triazole ring, was found to be the most active against the CaCo-2 cell line.

Absorption Characteristics and Quantum Yields of Singlet Oxygen Generation of Thioguanosine Derivatives

6-Thioguanine (1a) is considered to be photochemotherapeutic due to its specific characteristics of photosensitivity to UVA light and singlet molecular oxygen generation. To extend its phototherapeutic ability, two related thioguanines, 8-thioguanine (2a) and 6,8-dithioguanine (3a), have been designed and explored. Since the solubility of these thioguanines in dehydrated organic solvents is too poor to study, their triacetyl-protected ribonucleosides, that is, 2′,3′,5′-tri-O-acetyl-6-thioguanosine (1c), 2′,3′,5′-tri-O-acetyl-8-thioguanosine (2c) and 2′,3′,5′-tri-O-acetyl-6,8-dithioguanosine (3c) were prepared and investigated. The absorption maxima of 1c, 2c and 3c in acetonitrile were found at longer wavelengths than that of unthiolated guanosine (4c). Especially, 3c has the longest wavelength for absorption maximum and the highest value in terms of molar absorption coefficient among all thionucleobases and thionucleosides reported. These absorption properties were also well reproduced by quantum chemical calculations. Quantum yields of singlet oxygen generation of 2c and 3c were determined by near-infrared emission measurements to be as large as that of 1c. These results suggest that the newly synthesized thioguanosines, in particular 3c, can be further developed as a potential photosensitive agent for light-induced therapies.

Selective C8-Metalation of Purine Nucleosides via Oxidative Addition

8-Bromo-2′-deoxy-3′,5′-di-O-acetylguanosine (1), 8-bromo-2′,3′,5′-tri-O-acetylguanosine (2), 8-bromo-2′-deoxy-3′,5′-di-O-acetyladenosine (3), and 8-bromo-2′,3′,5′-tri-O-acetyladenosine (4) react with [Pd(PPh3)4] via a C8-Br oxidative addition to give the C8-palladated azolato complexes [5]-[8] featuring an unprotonated N7 ring nitrogen atom. The complexes feature diastereotopic trans-disposed triphenylphosphine ligands, which allowed the determination of 2JPP for complexes of the type trans-[PdL2(PPh3)2] (2JPP = 442 Hz for [7]). In addition, two complex molecules of [7] form a trans-Watson-Crick/Hoogsteen AA base pair in the solid state. N7-protonation of the guanosine-derived complexes [5] and [6] with HBF4·Et2O and of adenosine-derived complexes [7] and [8] using lutidinium triflate yields complexes [9]BF4 and [10]BF4 and complexes [11]OTf and [12]OTf bearing protic NH,NR-NHC ligands derived from guanosine and adenosine, respectively.

Synthesis of 8-alkoxy-6-alkylamino-2-alkylthiopurine nucleosides with a straightforward multiple-functionalization strategy

A straight forward strategy to synthesize purine nucleosides with multiple functionalization on 2-, 6-, and 8-positions has been developed successfully, which provides a series of 8-alkoxy-6-alkylamino-2-alkylthiopurine nucleosides in moderate to good yields for further biological and medical activity screening.

Synthesis and fluorescence properties of a full set of extended RNA base analogues

The synthesis and photophysical characterization of a complete set of fluorescent RNA base analogues derived by conjugating benzofuran moiety at the 5- and 8-positions of pyrimidine and purine bases, respectively, are described. Benzofuran-modified pyrimidine and purine ribonucleoside analogues exhibit contrasting fluorescence properties. Pyrimidine analogues are moderately emissive with emission maximum in the visible region, and importantly, are highly sensitive to solvent polarity and viscosity changes. On the other hand, purine analogues are highly emissive and are minimally affected by solvation and viscosity effects. Thorough photophysical analysis reveals that the pyrimidine and purine ribonucleosides displaying distinct and probe-like fluorescence properties could be useful in designing nucleic acid based biophysical tools to study nucleic acid structure and function.

An efficient and facile methodology for bromination of pyrimidine and purine nucleosides with sodium monobromoisocyanurate (SMBI)

An efficient and facile strategy has been developed for bromination of nucleosides using sodium monobromoisocyanurate (SMBI). Our methodology demonstrates bromination at the C-5 position of pyrimidine nucleosides and the C-8 position of purine nucleosides. Unprotected and also several protected nucleosides were brominated in moderate to high yields following this procedure.

RNA INCLUDING NUCLEOSIDE COMPOUND, METHOD FOR REGULATING AMOUNT OF PROTEIN PRODUCED FROM THE RNA, AND NUCLEOSIDE COMPOUND

An RNA of the present invention is an RNA containing a 5′ cap structure and a coding region having a 5′ initiation codon and a 3′ stop codon on both ends of the coding region, the RNA having a nucleoside compound introduced at a site selected from among the 5′ cap structure and 10 bases from a 5′ end of the RNA, wherein the nucleoside compound is such that a group is attached to (i) a carbon atom at position 8 of a purine nucleus or (ii) a carbon atom at position 5 or 6 of a pyrimidine nucleus, the group being represented by formula (I): [in-line-formulae]A-X═X-#??(I)[/in-line-formulae] where A represents an aryl group or a heteroaryl group, # represents a site where the group represented by the formula (I) is attached to the carbon atom at the position 8 of the purine nucleus or the carbon atom at the position 5 or 6 of the pyrimidine nucleus, and two Xs, which are identical to or different from each other, each represents a nitrogen atom or CH whose H may be substituted by alkyl.

2-Methylwyosine, a nucleoside with restricted anti conformation in the East region enforced by nucleobase moiety modification: Synthesis and conformational analysis by NMR and molecular dynamics

We synthesized a new 2-methyl derivative of wyosine using a multistep procedure starting from guanosine. We examined different synthetic paths and optimized the conditions for each step. Based on MD calculations and analysis of the 3 J HH and J C1′H1′ of the ribose moiety, we discovered that the sugar part adopted conformation specific for the East region rarely occurring in solution. This unusual conformational preference is probably due to steric repulsions between the methyl group at position 2 and the 5′-CH2OH group. We observed that N-glycosidic bond stability weakened 14-fold upon the introduction of the methyl group in position 2 compared with wyosine.