Preparation of 9-Substituted Pyridine-Stretched Adenines and Hypoxanthines

Crawford, Julia; Fraser, W. Hamish; Ramsden, Christopher A.

doi:10.1055/s-0028-1088028

Cited by 2 publications

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“…At the nucleoside level, hydrogenolysis of the 2-benzyloxy group 34 would give a concise route to 2'-deoxyisoguanosine from non-nucleoside precursors. At the DNA level, removal of the 2-allyloxy group using Noyori conditions 35 would give isoguanine 29 (Figure 2 right) for the study of its triplex-forming properties and also allow comparison between A, isoG, B and L. As the starting point for synthesis of the nucleoside intermediate 5, 36 we selected the well-known and widely used 6,29,[37][38][39][40][41] Hoffer sugar 2 (2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride). 42 Recently, we reported an improved synthesis of the Hoffer sugar that was achieved without need for distillation or chromatographic separation of intermediates, or the use of gaseous HCl.…”

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confidence: 99%

A concise synthesis of isoguanine 2ʹ-deoxyriboside and its adenine-like triplex formation when incorporated into DNA

Walsh¹,

Schwalbe²,

Fraser³

2021

Arkivoc

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A concise synthesis of 2'-deoxyisoguanosine is achieved whereby 2,6-dichloropurine is glycosylated using the Hoffer sugar to give a pair of beta-configured nucleoside N9/N7 regioisomers that are aminated using methanolic ammonia with concomitant deprotection of the sugar. Following chromatographic separation, pure 2-chloro-2'-deoxyadenosine was isolated as a single isomer. Displacement of the C2 chlorine atom using sodium benzyloxide, followed by hydrogenolysis of the benzyl group, gives 2'-deoxyisoguanosine. Isoguanine was incorporated into DNA by solid supported synthesis using the suitably protected 2-allyloxy-2'deoxyadenosine phosphoramidite with the allyl group being removed post-oligomerisation under Noyori conditions. DNA melting studies showed isoguanine to exhibit adenine-like triplex formation.

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Section: Introductionmentioning

confidence: 99%

A concise synthesis of isoguanine 2ʹ-deoxyriboside and its adenine-like triplex formation when incorporated into DNA

Walsh¹,

Schwalbe²,

Fraser³

2021

Arkivoc

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Synthetic approaches to imidazo[4,5-b]pyridine derivatives (review)

Bukhryakov

Kurkin

Yurovskaya

2011

Chem Heterocycl Comp

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Data on methods for the production of derivatives of imidazo [4,5-b]pyridines are reviewed.Keywords: imidazo [4,5-b]pyridines, diaminopyridine derivatives, annelation of pyridine ring, annelation of imidazole fragment, simultaneous formation of two condensed rings. The interest in imidazopyridines arises from their diverse biological activity. Data on the biological activity of imidazole derivatives were reviewed in [1]. They are analgesic [2] and nonsteroidal antiinflammatory agents [2, 3], exhibit antidepressant [4], cardiotonic [5], hypotensive, antiarrhythmic [6], and antisecretory [7] activity. Among compounds of this class antagonists of angiotensin II receptors that exhibit hypotensive activity are known [8,9]. In addition, a number of the imidazo[4,5-b]pyridines possess antiviral [10], antimicrobial [11], and cytotoxic [12] activities. Other aspects of the practical application of derivatives of imidazopyridines are known; for example, they are used in agriculture for the treatment of the shoots of broadleaved plants [13,14] and in the fight against rodents [15].A review of existing published data on methods for the synthesis of imidazo[4,5-b] pyridines derivatives is of undoubted interest in this connection. The information summarized in this review may be useful in the design and development of methods for the synthesis of functional derivatives of imidazopyridines and pyridopyrazines, which are prospective heterocyclic compounds for use in the search for new biologically active substances.The most useful starting compounds for the synthesis of imidazo [4,5-b]pyridines are the readily obtainable derivatives of 2,3-diaminopyridine, which are usually produced in two stages from the commercially available 2-chloro-3-nitropyridine [16] or 2-fluoro-3-nitropyridine [17]. The first stage involves nucleophilic substitution of the halogen in the pyridine ring activated by the nitro group. Reduction of the nitro group leads to the required derivative of 2,3-diaminopyridine, where the reducing agent is hydrogen in the presence of palladium on carbon [18], Raney nickel [19], sodium bisulfite, sodium borohydride, zinc, or iron in the presence of acid [19].

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Preparation of 9-Substituted Pyridine-Stretched Adenines and Hypoxanthines

Abstract: Please overwrite this text with a written abstract, which should summarize the results and conclusions of the research performed.

Cited by 2 publications

References 14 publications

A concise synthesis of isoguanine 2ʹ-deoxyriboside and its adenine-like triplex formation when incorporated into DNA

A concise synthesis of isoguanine 2ʹ-deoxyriboside and its adenine-like triplex formation when incorporated into DNA

Synthetic approaches to imidazo[4,5-b]pyridine derivatives (review)

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