A Simple Preparation of 1-Hydroxypyrene

Sehgal, Raj K.; Kumar, Subodh

doi:10.1080/00304948909356367

Cited by 17 publications

(23 citation statements)

References 4 publications

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“…A mixture of 2,2′-anhydrouridine 1 (0.30 g, 1.33 mmol) and 1-pyrenol 19 (0.86 g, 3.97 mmol) were reacted and purified as described above to afford nucleoside 2X (0.26 g, 44 %) as a pale yellow solid. R f : 0.4 (10% MeOH in CH 2 Cl 2 , v/v); MALDI-HRMS m / z 467.1217 ([M+Na] + , C 25 H 20 N 2 O 6 ·Na + , Calc.…”

Section: Methodsmentioning

confidence: 99%

High-Affinity DNA Targeting Using Readily Accessible Mimics of N2′-Functionalized 2′-Amino-α-L-LNA

et al. 2011

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N2′-Pyrene-functionalized 2′-amino-α-L-LNAs (Locked Nucleic Acids) display extraordinary affinity toward complementary DNA targets due to favorable preorganization of the pyrene moieties for hybridization-induced intercalation. Unfortunately, the synthesis of these monomers is challenging (~20 steps, <3% overall yield), which has precluded full characterization of DNA-targeting applications based on these materials. Access to more readily accessible functional mimics would be highly desirable. Here we describe short synthetic routes toward a series of O2′-intercalator-functionalized uridine and N2′-intercalator-functionalized 2′-N-methyl-2′-aminouridine monomers and demonstrate – via thermal denaturation, UV-visible absorption and fluorescence spectroscopy experiments – that several of them mimic the DNA-hybridization properties of N2′-pyrene-functionalized 2′-amino-α-L-LNAs. For example, oligodeoxyribonucleotides (ONs) modified with 2′-O-(coronen-1-yl)methyluridine monomer Z, 2′-O-(pyren-1-yl)methyluridine monomer Y or 2′-N-(pyren-1-ylmethyl)-2′-N-methylaminouridine monomer Q, display prominent increases in thermal affinity toward complementary DNA relative to reference strands (average ΔTm/mod up to +12 °C), pronounced DNA-selectivity, and higher target specificity than 2′-amino-β-L-LNA benchmark probes. In contrast, ONs modified with 2′-O-(2-napthyl)uridine monomer W, 2′-O-(pyren-1-yl)uridine monomer X or 2′-N-(pyren-1-ylcarbonyl)-2′-N-methylaminouridine monomer S display very low affinity toward DNA targets. This demonstrates that even conservative alterations in linker chemistry, linker length and surface area of the appended intercalators have marked impact on DNA-hybridization characteristics. Straightforward access to high-affinity building blocks such as Q/Y/Z is likely to accelerate their use in DNA-targeting applications within nucleic acid based diagnostics, therapeutics, and material science.

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Section: Methodsmentioning

confidence: 99%

High-Affinity DNA Targeting Using Readily Accessible Mimics of N2′-Functionalized 2′-Amino-α-L-LNA

et al. 2011

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“…All other chemicals were obtained from commercial sources at the highest grade available. 1‐Hydroxypyrene was synthesized by treating a dichloromethane solution of 1‐pyrenecarboxaldehyde with m ‐chloroperbenzoic acid, a saturated NaHCO 3 solution, and then a KOH solution according to the procedure by Sehgal and Kumar . The 1‐(methoxy‐substituted naphthalene‐1‐ylmethyloxy)pyrene derivatives ( 1a and 1b ) were synthesized using the following procedure.…”

Section: Methodsmentioning

confidence: 99%

“…1-Hydroxypyrene was synthesized by treating a dichloromethane solution of 1pyrenecarboxaldehyde with m-chloroperbenzoic acid, a saturated NaHCO 3 solution, and then a KOH solution according to the procedure by Sehgal and Kumar. 16 The 1-(methoxy-substituted naphthalene-1-ylmethyloxy)pyrene derivatives (1a and 1b) were synthesized using the following procedure. After sodium hydride (60% purity) was slowly added to an N,Ndimethylformamide (DMF) solution of 1-hydroxypyrene with stirring, 1-chloromethyl-2-methoxynaphthalene and 1chloromethyl-4-methoxynaphthalene, obtained via chlorination of the corresponding methoxy-substituted 1-hydroxymethylnaphthalene with thionyl chloride, was allowed to react with the hydroxypyrene-derived sodium salt for 5 h at room temperature.…”

Section: Materials and Solventsmentioning

confidence: 99%

Nonsalt 1‐(arylmethyloxy)pyrene photoinitiators capable of initiating cationic polymerization

Uchida

Nakano

Igarashi

et al. 2014

J of Applied Polymer Sci

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Analysis of photoproducts derived from 1‐(methoxynaphthalen‐1‐ylmethyloxy)pyrene initiators and polymer end groups demonstrated that methoxynaphthalen‐1‐ylmethyl carbocation is involved in the initiation steps for both styrene (St) and cyclohexene oxide (CHO) polymerization. Charge transfer from the pyrenyloxy oxygen atom to the methoxynaphthalen‐1‐ylmethyl chromophore in the singlet excited state is assumed to be responsible for the efficient generation of the carbocation species, which also initiates the copolymerization of St and CHO. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 40510.

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“…1-Hydroxypyrene (5) [34]. Pyrene carboxaldehyde (10.0, 43.4 mmol) and m-chloroperbenzoic acid (11.31 g, 65.5 mmol) were dissolved in dry methylene chloride and refluxed with stirring under argon atmosphere for 24 h. The solution was concentrated at reduced pressure to give a red-brown residue.…”

Section: Synthesis Of Monomers and Oligomers (Terthiophenes And Quatementioning

confidence: 99%

Synthesis, characterization and optical properties of novel oligothiophenes bearing pyrene units attached via well defined oligo(ethylene glycol) spacers

et al. 2015

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A Simple Preparation of 1-Hydroxypyrene

Cited by 17 publications

References 4 publications

High-Affinity DNA Targeting Using Readily Accessible Mimics of N2′-Functionalized 2′-Amino-α-L-LNA

High-Affinity DNA Targeting Using Readily Accessible Mimics of N2′-Functionalized 2′-Amino-α-L-LNA

Nonsalt 1‐(arylmethyloxy)pyrene photoinitiators capable of initiating cationic polymerization

Synthesis, characterization and optical properties of novel oligothiophenes bearing pyrene units attached via well defined oligo(ethylene glycol) spacers

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