Solid-Phase Synthesis of 5′-Deoxy-5′-Amino-Clitocine Analogues

Varaprasad, Chamakura V.N.S.; Habib, Qazi; An, Hongyu; Hong, Zhi

doi:10.1080/15257770500379066

Cited by 3 publications

(1 citation statement)

References 17 publications

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“…The oxazoline analogue (99) exhibited a potency which was comparable to that of clitocine, whereas the hydroxyethyl amide analog (100), obtained as a minor product, was found to be inactive. By using solid-phase reaction technologies, various 5 0 -deoxy-5 0 -amino derivatives of nucleosides were prepared in a parallel manner (Scheme 22.13) [21]. After attaching the amino sugar (110) to polystyrene monomethoxytrityl chloride, reduction of the azido group provided 112, which was condensed with 4,6-dichloro-5-nitropyrimidine to yield the key intermediate (113).…”

Section: Clitocine Analogues J581mentioning

confidence: 99%

Clitocine and Its Analogues

Shin¹,

Min²

2008

Modified Nucleosides

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Guided by the insecticidal activity against the agricultural pest insect Pectinophora gossypiella, Kubo and Kim isolated clitocine (1a) [1], along with adenosine, from Clitocybe inversa, a medium-sized, buff-colored mushroom found in western North America. The NMR spectral data for clitocine was found to be very similar to that of adenosine, with the exception of the absence of the C-8 carbon peak of adenosine, while the low chemical shift of the 4-NH proton suggested strong hydrogen bonding between the 5-NO 2 and 4-NH groups. Later, Moss and coworkers [2] confirmed its structure through X-ray crystallographic analysis: as postulated earlier by Kubo et al., the entire aglycone moiety resembles a tricyclic ring system as a result of the hydrogen bonding between the 4-NH and 6-NH protons and the NO 2 group. SynthesisThe interesting biological activity of clitocine, together with its biogenetically close relationship to adenosine, triggered an immediate attempt to synthesize the molecule de novo. Two years after its initial isolation, two independent syntheses have now been completed. The first synthesis [3] is based upon the condensation of 2,3,5-tribenzoylribofuranosylamine (2) with 4,6-dichloro-5-nitropyrimidine (3) in the presence of a base to give a mixture of the a-and b-anomers in a 7 : 1 ratio (Scheme 22.1), although the yield (19%) is relatively poor. Deprotection of the benzoate group of 4 using a methanolic ammonia solution produced clitocine with a 71% yield. In order to improve the efficiency and reproducibility of the coupling reaction, an acetonideprotected amino sugar (5) was employed for the coupling reaction with 4-chloro-5-Modified Nucleosides: in Biochemistry, Biotechnology and Medicine. Edited by Piet Herdewijn

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Section: Clitocine Analogues J581mentioning

confidence: 99%

Clitocine and Its Analogues

Shin¹,

Min²

2008

Modified Nucleosides

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Anticancer properties and mechanism of action of the fungal nucleoside clitocine and its derivatives

Bailly

2024

European Journal of Medicinal Chemistry Reports

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Polymer-Assisted Structural Modification on Nucleosides and Nucleotides

Zhao

Zhang

2013

Nucleosides, Nucleotides and Nucleic Acids

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Nucleosides and their analogues play important roles in biological research and clinical therapeutics. Polymer-assisted structural modifications of nucleosides and nucleotides enable parallel and rapid construction of nucleoside library. For some nucleosides, higher chemical selectivity and regioselectivity can be achieved using solid-phase synthesis when compared to classic solution-phase synthesis.

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Solid-Phase Synthesis of 5′-Deoxy-5′-Amino-Clitocine Analogues

Cited by 3 publications

References 17 publications

Clitocine and Its Analogues

Clitocine and Its Analogues

Anticancer properties and mechanism of action of the fungal nucleoside clitocine and its derivatives

Polymer-Assisted Structural Modification on Nucleosides and Nucleotides

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