• Bulletin of the Korean Chemical Society
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• 제22권7호
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• pp.761-764
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• 2001

• Bulletin of the Korean Chemical Society
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• 제30권12호
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• pp.2989-2992
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• 2009

An efficient synthetic route of novel 2′(${\alpha}$)-C-fluoro-2′(${\beta}$)-C-methyl carbocyclic nucleoside analogues is described. The key fluorinated intermediate 7 was prepared from the epoxide intermediate 5 via selective ring-opening of epoxide. Coupling of 7 with nucleosidic bases under the Mitsunobu reactions followed by deprotection afforded the target carbocyclic nucleoside analogues. The synthesized compounds were evaluated as inhibitors of the hepatitis C virus (HCV) in Huh-7 cell line in vitro.

• Rapid Communication in Photoscience
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• 제3권4호
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• pp.76-78
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• 2014

Fluorescent nucleic acids were prepared utilizing the polymerase extension (PEX) reaction to incorporate fluorescent molecules. 2'-Deoxyuridine triphosphate (dUTP) derivatives possessing pyrene molecules as fluorophores were synthesized using the aqueous-phase Sonogashira coupling between 5-Iodo-dUTP and acetylene-linked pyrene molecules. The incorporation of the pyrene (Py)-labeled deoxyuridine triphosphates (PyU) into DNA by polymerase was evaluated by polyacrylamide gel electrophoresis, demonstrating that the PyU can work as a good substrate for the PEX reaction. The fluorescent properties of the functionalized DNA prepared by the PEX reaction were characterized by steady-state fluorescence measurements. The Py-conjugated DNA showed typical emission spectra of the pyrene, and the DNA with two pyrene molecules connected to each other by a diethylene glycol linker exhibited a broadened emission attributed to the electronic interaction between the Py molecules.

• Archives of Pharmacal Research
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• 제27권11호
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• pp.1099-1105
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• 2004

The peroxisome proliferator-activated receptors (PPARs) are a primary regulator of lipid metabolism. Potency for activation of PPAR$\gamma$, one of a subfamily of PPARs, particularly mirrors glucose lowering activity. We prepared thiazolidinediones featuring benzoxazole moiety for subtype selective PPAR$\gamma$ activators. 5-[4-[2-(Benzoxazol-2-yl-alkylamino)ethoxy]benzyl]thiazolidine-2,4-diones have been prepared by Mitsunobu reaction of benzoxazolylalkylaminoethanol 8 and hydroxybenzylthiazolidinedione 6 and their activities were evaluated. Most compounds tested were identified as potent PPAR$\gamma$ agonists.

• 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 $\mu M$.

• Bulletin of the Korean Chemical Society
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• 제27권11호
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• pp.1910-1912
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• 2006

• Bulletin of the Korean Chemical Society
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• 제35권9호
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• pp.2743-2748
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• 2014

Novel 4'-trifluoromethyl-5'-norcarbocyclic purine phosphonic acid analogs were efficiently synthesized from commercially available 1,3-dihydroxy cyclopentane (5). Trifluoromethylation was successfully performed by using the Ruppert-Prakash reaction. The purine nucleosidic bases were efficiently coupled by using the Mitsunobu reaction. The synthesized adenosine phosphonic acids analogs 13 and 16 were screened for antiviral activity against human immunodeficiency virus-1 (HIV-1). Adenine derivative 13 exhibited significant anti-HIV-1 activity.

• Bulletin of the Korean Chemical Society
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• 제20권12호
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• pp.1421-1427
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• 1999

4-Hydroxy-4'-methoxyazobenzene and 4-hydroxy-4'-cyanoazobenzene were synthesized from phenol with p-anisidine and p-aminobenzonitrile through a diazotization reaction, respectively. They were reacted with 2-chloroethanol, 2-(2-chloroethoxy)ethanol, or 2-[2-(2-chloroethoxy)ethoxy]ethanol to produce six kinds of new mesogenic alcohols having an azobenzene group that is sensitive to the ultraviolet. Twelve kinds of new photoresponsive monomers with two symmetrical mesogens were prepared by the reaction of the mesogenic alcohols with fumaric acid or maleic acid through a Mitsunobu reaction. The resulting monomers have different length of flexible ethyleneoxy spacer tethered to azobenzene group. The length of the spacer affected their thermal stability, solubility, and phase transition temperature. Structures of the monomers were identified by FT-IR and ¹H-NMR spectra. Their phase transition temperatures and thermal stability were also investigated by a differential scanning calorimetry (DSC) and a thermogravimetric analysis (TGA). From an optical polarizing microscopy, all the prepared monomers except fumarate-1 and maleate-1 were found to show enantiotropic liquid crystallinity with a smectic texture like focal-conic, fan-shaped, and batonnet textures.

• 한국광학회지
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• 제10권3호
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• pp.188-194
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• 1999

Mitsunobu 반응을 이용하여 전기광학계수 $\gamma_{33}$크고 열적 .시간적으로 안정적인 폴리이미드(polyimide)계고분자 용액인 PI-SOT(폴리이미드계 4-[N,N-bis(hydroxyethyl)amino­4'­($\beta$­cyano-$\beta$­methylsulfonyl)vinyl]azobenzene)고분자를 합성하였다. C.C. Teng의 단순반사법을 이용하여 코로나 폴링으로 극성 배향시킨 PI-SOT 박막의 전기광학계수 $\gamma_{33}$의 열안정성 및 시간안정성을 파장 632.8 nm와 852nm에서 측정하였다. 그 결과 상온에서 전기광학계수$\gamma_{33}$은 파장 632.8nm서 25.12 pm/V이고, 852 nmsns 5.40pm/V였다. 이 값들은 상온에서 60일 이상 장기간 안정적으로 유지되었으며, $100^{\circ}C$의 고온에서도 10시간내에서 6% 이내로 안정된 값을 유지하였다.

• 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 $100{\;}{\mu}M$.