• Archives of Pharmacal Research
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• 제23권6호
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• pp.559-563
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• 2000

Novel exomethylene cyclopropyl nucleosides were synthesized as potential antiviral agents. The key intermediate 5 was synthesized in 4 steps, from Feists acid 1 and was condensed with purine derivatives by the $S_N2$ type reaction to give some cyclopropyl nucleosides. The synthesized nucleosides did not showed any significant antiviral activity against HSV-1, HSV-2, HCMV, HIV-1, HIV-2, and HBV up to 100 $\mu\textrm{m}$.

• Bulletin of the Korean Chemical Society
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• 제25권2호
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• pp.221-225
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• 2004

A series of 2',3'-dideoxy-3'-fluoro-D-apiosyl nucleosides 15, 16, 17 and 18 were synthesized enantiomerically with L-Gulonic- ${\gamma}$-lactone as the starting material. The reduction of butenolide 1 with DIBAL-H followed by the Luche procedure afforded the allylic alcohol 2. Ozonolysis and the reduction of compound 4 induced the cyclized lactol, which was acetylated to give the acetate 7. Condensation of the acetate 7 with silylated pyrimidine ($N^4$-benzoyl cytosine) and a purine base (6-chloropurine) under Vorbruggen conditions and deblocking afforded a series of fluorinated apiosyl nucleosides.

• 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.341.1-341.1
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• 2002

Apio nucleosides belong to unique classes of nucleosides in that 4'-hydroxymethyl group moves to 3'-position. Among thse compounds. we found that apio dideoxyadenosine (apio-ddA) exhibited potent antiviral activity and apio-d4A showed potent anti-HCMV activity. Based on thse findings. it was of great interest to design and synthesize Anio nucleoside anlogues with various substituents such as fluorn or azido group. In order to synthesize apio analogues. the glyxosyl dondr. D-. and L-apio sugar acetates were first synthesized. starting from D-gallas. condensed whth silylated N4-benzoylcytosine. and then convenged to the linal D-andL-nucleosides. Synthesist of the D-and-apio nucieosides will be prssented in detail aht th the meeting.

• Bulletin of the Korean Chemical Society
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• 제30권10호
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• pp.2309-2317
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• 2009

Depurination, the release of purine bases from nucleic acids by hydrolysis of the N-glycosidic bond, gives rise to alterations of the cell genome. Though cells have evolved mechanisms to repair these lesions, unrepaired apurinic sites have been shown to have two biological consequences: lethality and base substitution errors. 2-Bromopropane (2-BP) is used as an intermediate in the synthesis of pharmaceuticals, dyes, and other organics. In addition, 2-BP has been used as a replacement for chloroflurocarbons and 1,1,1-trichloroethane as a cleaning solvent in electronics industry. However, 2-BP was found to cause reproductive and hematopoietic disorders in local workers exposed to it. Owing to the toxicity of 2-BP, there has been a tendency to use 1-BP as an alternative cleaning solvent to 2-BP. However, 1-BP has also been reported to be neurotoxic in rats. Though $N^7$-guanine adduct of 2-BP has been reported previously, massive depurination of the nucleosides and calf thymus DNA was observed in this study. We incubated the nucleosides (ddG, dG, guanosine, ddA, dA and adenosine) with excess amount 2-BP at the physiological condition (pH 7.4, $37\;{^{\circ}C}$), which were analyzed by HPLC and LC-MS/MS. In addition, the time and dose response relationship of depurination in nucleosides induced by 2-bromopropane at the physiological condition was investigated. Similarly, incubation of calf-thymus DNA with the excess amount 2-BP at the physiological condition was also performed. In addition, the time and dose response relationship of depurination in calf-thymus DNA induced by 2-BP at the physiological condition was investigated. Those results suggest that the toxic effect of 2-BP could be both from the depurination of nucleosides and DNA adduct formation.

• 생약학회지
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• 제16권4호
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• pp.239-242
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• 1985

The anion of $6-benzenesulfonyl-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-{\alpha}-d-glucofuranose$ was stable and reacted with carbon electrophiles to give higher-carbon sugars. Reactions of uridine 5'-aldehyde with phosphoranes afforded heptofuranose nucleosides.

• 약학회지
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• 제47권6호
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• pp.417-421
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• 2003

This paper describes a synthetic route to novel 2'-methyl and 4'-hydroxy carbocyclic nucleosides. The methyl group was successfully installed by carbonyl addition reaction of isopropenyl magnesium bromide followed by ring-closing metathesis and the hydroxy group was directly introduced from carbohydrate chiral template "D-lactose".ose".uot;.

• Bulletin of the Korean Chemical Society
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• 제8권3호
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• pp.171-173
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• 1987

Some pyridazin-6-one nucleosides have been prepared directly without silylation of heterocyclic base using iodine catalyst, a new type Friedel-Crafts catalyst.

• Archives of Pharmacal Research
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• 제25권6호
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• pp.790-794
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• 2002

A series of novel exomethylene cyclopropyl nucleosides have been synthesized starting from Feist's acid. Classical nucleophilic substitution conditions ($K_2CO_3$, 18-crown-6) of the tosylate 2 as well as Mitsunobu reaction (DEAD, $PPh_3$) of alcohol 1 with pyrimidine bases afforded a series of novel cyclopropyl nucleosides. Compound 4b displayed moderate anti-HBV activity without any cytotoxicity up to $100{\;}{\mu}M$.

• Archives of Pharmacal Research
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• 제21권3호
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• pp.338-343
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• 1998

$2^1$-Fluorohexopyranosyl nucleosides 1a and 1b which contained a bioisosteric double bond and a fluorine were synthesized in 12 steps, starting from D-galactose. During diethylaminosulfur trifluoride (DAST) fluorination, retention of stereochemistry was observed through the participation of methoxy or chloro group at the 6-posiition of the purine base. The final nucleosides 1a and 1b were found to be inactive against HIV-1 and HSV-1,2.

• Bulletin of the Korean Chemical Society
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• 제33권12호
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• pp.4007-4014
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• 2012

Efficient synthetic route to novel 4'-fluorinated 5'-deoxythreosyl phosphonic acid nucleosides was described from glyceraldehyde using Horner-Emmons reaction in the presence of triethyl ${\alpha}$-fluorophosphonoacetate. Glycosylation reaction of nucleosidic bases with glycosly donor 14 gave the nucleosides which were further phosphonated and hydrolyzed to reach desired nucleoside analogues. Synthesized nucleoside analogues 18, 21, 25 and 28 were tested for anti-HIV activity as well as cytotoxicity. Adenine derivatives 18 and 21 showed significant anti-HIV activity up to $100{\mu}M$.