Synthesis of and its 4′-thio analog as potential antiviral agents

Kikuchi, Yo; Kurata, H.; Nishiyama, Shigeru; Yamamura, Shosuke; Kato, Kuniki

doi:10.1016/s0040-4039(97)01035-6

Cited by 12 publications

(5 citation statements)

References 15 publications

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“…Recently [57] aQ [58] aR aS [60] aT [61] aU [62] aY [66] aZ [67] bA [68] bB [69] bC [70] bF [73] bG [74] aV [63] aX [65] aW [64] bE [72] bD [71] Since the naturally occurring purine nucleoside analog oxetanocin A 9 and its derivative COXT-G 10 have been found to be effective as anti-HIV-1 and anti-herpes virus agents, the syntheses of different types of hydroxymethylbranched nucleosides (the so-called ring-enlarged oxetanocin A analogs) have been reported (Fig. 11).…”

Section: Isoxazolidinyl Nucleosides [52]mentioning

confidence: 99%

“…Compound 188, obtained in three steps from commercially available diacetone D-glucose, was benzoylated at the primary alcohol function, followed by the selective removal of the 5,6-isopropylidene moiety, afforded intermediate diol 2',3'-Dideoxy-2',3'-bis-C-hydroxymethylnucleosides of Type aU were prepared from 223 by Kato et al [62]. Hydroboration of the exocyclic double bond in 224, using BH 3 ·SMe 2 in THF, followed by oxidation of the resulting alkylborane with alkaline peroxide, afforded enantiomerically pure C-2 symmetric hydroxymethyl diester 226.…”

Section: Isoxazolidinyl Nucleosides [52]mentioning

confidence: 99%

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Sugar-Modified Nucleosides in Past 10 Years, A Review

Ichikawa¹,

Kato

2001

CMC

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179

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In the search for effective, selective, and nontoxic antiviral and antitumour agents, a variety of strategies have been devised to design nucleoside analogs. These strategies have involved several formal modifications of the naturally occurring nucleosides, especially, alteration of the carbohydrate moiety. Since the naturally occurring purine nucleoside analog oxetanocin A and its derivatives have been found to be effective as anti-HIV-1 and anti-herpes virus agents in 1986, the syntheses of different types of sugar-modified nucleoside analogs have been reported. In this review we will give an overview of the sugar-modified nucleosides synthesized since the late 1990 according to their structural types along with the synthetic routes of some selected nucleosides.

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Section: Isoxazolidinyl Nucleosides [52]mentioning

confidence: 99%

Section: Isoxazolidinyl Nucleosides [52]mentioning

confidence: 99%

Sugar-Modified Nucleosides in Past 10 Years, A Review

Ichikawa¹,

Kato

2001

CMC

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179

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“…41 Compounds 23a−c, which may be considered as ring-expanded oxetanocin analogues, and unusual azasugar nucleosides 24a−c are inactive against HIV-1, HSV-1, and HSV-2. 42,43 Likewise, the 2′-azido and fluoro analogues 25a,b were found inactive against a panel of viruses. 27,28 This was also the case for the racemate of 26 and its anomers.…”

Section: Nucleosides With a Transposed 4′-hydroxymethyl Groupmentioning

confidence: 97%

“…44 The 4′-thio analogues 27a,b are inactive against HIV-1, HSV-1, and HSV-2. 42,43 No biological data have been reported for compounds 28a,b and their enantiomers. 45 Compound 29a (Figure 8) shows interesting activity against HIV (EC 50 = 2.55 μM).…”

Section: Nucleosides With a Transposed 4′-hydroxymethyl Groupmentioning

confidence: 99%

“…27,28 Replacement of the 2′-OH functionality with an additional hydroxymethyl group led to branched nucleoside analogues of oxetanocin (23, 24, and 27), prepared in a stereospecific fashion from a chiral epoxide readily available from (+)-diethyl L-tartrate. 42,43 Additional structural modifications comprise the synthesis of cyclopropane-fused ring systems, 40,41 an example of which being the north-locked 2′-oxabicyclo[3.1.0]hexyl nucleosides 20 and 21 reported by Moon et al 40 The strategy, shown in Scheme 13, entailed the use of a tandem alkylation− lactonization reaction to convert (S)-epichlorohydrin (197) into the corresponding lactone ester 198 upon treatment with diethyl malonate and sodium metal. Sterically driven hydrolysis of the lactone moiety followed by ester reduction proceeded chemoselectively through intermediate 199, which in the presence of acid recyclized to give 200.…”

Section: Apio-and 2′-and 3′-deoxyapionucleosidesmentioning

confidence: 99%

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Nucleosides with Transposed Base or 4′-Hydroxymethyl Moieties and Their Corresponding Oligonucleotides

et al. 2015

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This review focuses on 4'-hydroxymethyl- or nucleobase-transposed nucleosides, nucleotides, and nucleoside phosphonates, their stereoisomers, and their close analogues. The biological activities of all known 4'-hydroxymethyl- or nucleobase-transposed nucleosides, nucleotides, and nucleoside phosphonates as potential antiviral or anticancer agents are compiled. The routes that have been taken for the chemical synthesis of such nucleoside derivatives are described, with special attention to the innovative strategies. The enzymatic synthesis, base-pairing properties, structure, and stability of oligonucleotides containing nucleobase- or 4'-hydroxymethyl-transposed nucleotides are discussed. The use of oligonucleotides containing nucleobase- or 4'-hydroxymethyl-transposed nucleotides as small oligonucleotide (e.g., human immunodeficiency virus integrase) inhibitors, in applications such as antisense therapy, silencing RNA (siRNA), or aptamer selections, is detailed.

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Synthesis Of Nucleosides

Vorbrüggen¹,

1999

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This chapter deals with the synthesis of nucleosides (e.g., the formation of N ‐glycosides of sugars such as D ‐ribose or 2‐deoxy‐D‐ribose with heterocyclic nitrogen bases). The methods of nucleoside synthesis have been treated in a number of reviews and monographs. It is now generally accepted that nucleosides were among the first organic compounds formed at the start of evolution in the early history of our planet earth. To support this point, guanine and adenine were heated with D ‐ribose in seawater, which contains the Lewis acid magnesium chloride as catalyst. One thus obtained the nucleosides guanosine and adenosine together with comparable yields of unnatural α‐nucleosides. The latter were gradually photoanomerized to the thermodynamically more stable compounds in overall yields of 5–6%. The furanose form of ribose reacts faster than the pyranose form. Corresponding syntheses of the pyrimidine nucleosides uridine and cytidine from uracil , cytosine and ribose are more problematic and remain an enigma. The recent conversion of glycolaldehyde‐ O ‐phosphate and formaldehyde to ribose‐2,4‐di‐ O ‐phosphate might give new insights into the prebiotic syntheses of uridine and cytidine. The evidence and hypotheses for these prebiotic conversions and the evolution of RNA, as well as the implications of an “RNA World,” have been reviewed. These RNA nucleosides are reduced in vivo as 5′‐ O ‐diphosphates by ribonucleotide reductases to the corresponding 2′‐deoxynucleosides—the building blocks of DNA such as 2′‐deoxyguanosine. The thermodynamically controlled synthesis of these four building blocks of RNA has implications for the design of efficient, high yielding, new methods for the synthesis of the naturally occurring nucleosides, nucleoside antibiotics, and modified nucleosides that may serve as antimetabolites to fight viral and parasitic diseases and cancer. The nucleoside rings in this chapter are depicted arbitrarily in the anti conformation, as occurs predominantly in the crystal and solution (based primarily on NOE‐ 1 H‐ and 13 C‐NMR measurements) forms of pyrimidine nucleosides. Only a few nucleosides, such as 6‐methyluridine, occur with the heterocyclic ring predominantly in the syn conformation. The synthesis of C ‐nucleosides has been reviewed previously and is not covered in this review.

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Synthesis of and its 4′-thio analog as potential antiviral agents

Cited by 12 publications

References 15 publications

Sugar-Modified Nucleosides in Past 10 Years, A Review

Sugar-Modified Nucleosides in Past 10 Years, A Review

Nucleosides with Transposed Base or 4′-Hydroxymethyl Moieties and Their Corresponding Oligonucleotides

Synthesis Of Nucleosides

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