• Bulletin of the Korean Chemical Society
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• 제33권10호
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• pp.3417-3422
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• 2012

A new method for the construction of 3-aminoindole nucleosides of 2-acetamido-2-deoxy-D-glucose based is presented. Nitration and acetylation of the indole nucleosides by acetic anhydride-nitric acid mixture followed by reduction using silver catalyst (SNSM) impregnated on silica gel, afforded the corresponding amino indole nucleosides. The nucleosides were tested for antiviral activity against hepatitis B virus (HBV) to show different degrees of antiviral activities or inhibitory actions.

• 약학회지
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• 제35권6호
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• pp.530-554
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• 1991

The synthetic methodologies for the preparation of C-nucleosides are divided into four categories, and each category is discussed in details. The chemical rections which lead to other C-nucleosides from preformed the natural product pseudouridine are described first, followed by synthesis of C-nucleosides by condensation of pre-formed heterocyclic base with sugar, and by construction of heterocyclic base from a carbohydrate intermediate that bear functional carbon fragment at the anomeric position. Finally, methods of total synthesis of C-nucleosides from carbohydrate and achiral starting materials are presented.

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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• pp.346.2-346.2
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• 2002

Recently, several branched-nucleosides have been synthesized and evaluated as potent antitumor or antiviral agents. Among them, 4'${\alpha}$--C-ethenyl and 4'${\alpha}$-C-ethynyl nucleosides which having an additional double or triple bond at 4'-position were reported to be as potent antiviral and anlitumor activities. Encouraged by these interesting structures and antiviral activities, it was determined to synthesize novel classes of nucleosides comprising branched carbocyclic nucleosides with an additional aryl group at 4'${\alpha}$-position using versatile reiterative three-step sequences from simple acyclic precursor '2-hydroxyacetophenone. Our efforts toward the synthesis of novel nucleosides analogues are reported herein.

• Journal of Nutrition and Health
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• 제31권4호
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• pp.679-686
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• 1998

This study was performed to determine whether the infusion of nucleosides and a nucleotide mixture directly ito intestinal lumen can induce a regenerative effect on impaired intestinal mucosa. The effects of massive small bowel resention and also total parenteral nutrition were induced by surgical creation of Thirty-Vella fistual in male Sprague-Dawley rats. The rats received saline solution (Control group) or nucleosides and a nucleotide mixture(lower concentration group(Nucl) or higher concentration group (Nuc2) every two days into the fistula. Mucosal protein, DNA , ornithine decarboxylase(ODC) activity, and morphometry were evaluated at 9 or 21 days postoperation in the fistual and also in the residual ileal segment. On the 9th day, mucosal protein, DNA content, and villous surface area in the fistula and also in the residual ileum increased in rats that received nucleosides and a nucleotide mixture of lower concentration (Nuc 1). On the 21 th day, there were no significant differences in intestinal mucosa between the control group and the lower level nucleoside nucleotide mixture-treated group. The fistula villous height of the higher nucleosides and a nucleotide mixture group was higher than in the control rats. Fistula mucosal ODC activities were not significantly different between groups although the mucosal ODC activity of the residual ileal segment was increased on the 9th day. Our data suggests that this animal model is suitable for studying the effect of dietary factors on intestinal mucosal growth and regeneration after villous stropy , differentiating direct effects of diet on the intestine from systemic effects. It is also suggested that external nucleosides and nucleotides have supportive effects on intestinal mucosal regeneration.

• Bulletin of the Korean Chemical Society
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• 제30권10호
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• pp.2318-2328
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• 2009

Massive deadenylation of adenine based-nucleosides induced by halogenated alkanes at the physiological condition have been observed. For the study of deadenylation effects by the different substituents and/or functionality in halogenated alkanes, diverse kinds of halogenated alkanes were incubated with adenine based-nucleosides (ddA, dA and adenosine) for 48 h at the physiological condition (pH 7.4, $37\;{^{\circ}C}$), which were analyzed by HPLC and further confirmed by LC-MS. Among the sixteen different halogenated alkanes, we observed massive deadenylation of nucleosides by 2-bromo-2-methylpropane, 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane. The order of deadenylation rate was highest in 2-bromo-2-methylpropane followed by 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane. In addition, time and dose response relationship of deadenylation in adenine based-nucleosides induced by 2-bromo-2-methylpropane, 2,3-dibromopropene, 2-bromopropane, bromoethane and 2-iodopropane at the physiological condition were investigated. In addition, deadenylation of calf thymus DNA induced by halogenated alkanes was also investigated. These results suggest that the toxic effect of certain halogenated alkanes might be from the depurination of nucleosides.

• Archives of Pharmacal Research
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• 제26권11호
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• pp.887-891
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• 2003

Novel trans-2,2-dimethylcyclopropyl nucleosides were synthesized as potential antiviral agents. The key intermediate, 3, was synthesized via five steps from ethyl chrysanthemate and condensed with purine bases using the Mitsunobu reaction to give six cyclopropyl nucleosides. These synthesized nucleosides did not show any significant antiviral activity against HSV-1, HSV-2, EMCV, Cox B3, or VSV, at concentrations up to 100 $\mu M$.

• 약학회지
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• 제47권5호
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• pp.271-275
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• 2003

Easy and efficient synthetic route of novel 4'-C methyl branched carbocyclic nucleosides is described. The installation of alkyl and aryl groups at 4'-position of carbocyclic nucleosides were successfully made via sequential [3,3]-sigmatropic rearrangement and ring-closing metathesis (RCM) starting from simple ketones such as acetol. Adenine and uracil were coupled via Pd(0) catalyzed reaction, followed by desilylation to give novel compounds 13 and 14, respectively.

• Archives of Pharmacal Research
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• 제26권9호
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• pp.679-685
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• 2003

A series of novel cyclopropyl nucleosides was synthesized using the highly stereoselective Simmons-Smith reaction starting from 1,2:5,6-di-Ο-isopropylidene-D-mannitol. The structural assignments of these nucleosides were determined by NMR studies and X-ray crystallography. All the synthesized nucleosides were assayed against several viruses.

• 한국식품영양과학회지
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• 제26권1호
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• pp.130-136
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• 1997

250g내외의 횐쥐에게 Thiry-Vella fistula를 만든 후 수술과 비경구 영양 효과로 인하여 위축되는 소장의 누공에 각각 nucleosides/nucleotide혼합용액 (Nuc군)이나 glutamine(Gln군), glycine(Gly군)등을 투여하여 소장 점막의 위축 방지나 재생효과가 있는지를 알아보고 자 실험하여 다음과 같은 결과를 얻었다. Thiry-Vella fistula 시술 후 9일 동안 2일에 한 번씩 총 4회 소장 누공으로 주입한 이미노산들과 nucleosides/nucleotide 혼합물의 효과는 누공의 소장 점막에 미치는 직접적인 효과와 비누공 부분에 대한 간접적인 효과로 나누어 볼 수 있다. Nucleosides/nucleotide 혼합물은 소장 누공으로 주입되어 직접 접촉되는 부분의 소장 DNA함량을 유의적으로 증가 시켰으며 단백질 함량도 높은 수치를 보여 주었고 조직 검사 결과 소장 융모의 길이와 표면적을 증가시킨 것으로 나타났다. 그러나 ［$^3$H］ thymidine incorporation의 결과는 대조군과 유의적인 차이를 보이지 않았다. Glycine은 소장 단백질과 DNA에 있어서 대조군보다는 높고 Nuc군보다는 낮은 경향을 보여 주었으나 ［$^3$H］-thymidine incorporation은 누공과 비누공부분에서 모두 가장 높게 나타났으며 특히 비누공부분에서는 유의적으로 증가되어 있었다. Glutamine의 효과는 glycine 투여 효과와 비슷하거나 오히려 떨어지는 것으로 나타났다.

• Archives of Pharmacal Research
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• 제6권1호
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• pp.79-81
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• 1983

Several potent anti-herpes virus nucleosides, 2'fluoro-2'-deoxyarabinofuranosyl pyrimidine nucleosides, were prepared in good yields by a new condensation method using sodium iodide and a new solvent system, and FMAU could be also prepared directly from thymine by this method.