• Journal of Integrative Natural Science
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• v.8 no.3
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• pp.153-163
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• 2015

Racemic synthesis of novel 5',5'-difluoro-2'-methyl-apiose nucleoside phosphonic acid analogs was achieved as potent antiviral agents. Phosphonation was performed by direct displacement of triflate intermediate with diethyl (lithiodifluoromethyl) phosphonate to give the corresponding (${\alpha},{\alpha}$-difluoroalkyl) phosphonate. Condensation successfully proceeded from a glycosyl donor with persilylated bases to yield the nucleoside phosphonate analogs. Deprotection of diethyl phosphonates provided the target nucleoside analogs. An antiviral evaluation of the synthesized compounds against various viruses such as HIV, HSV-1, HSV-2 and HCMV revealed that the pyrimidine analogs (cytosine, uracil, and thymine) have weak anti-HIV or HCMV activity.

• Bulletin of the Korean Chemical Society
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• v.31 no.6
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• pp.1643-1648
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• 2010

Adenosine 5'-phosphonates have been reported as potential chain terminators against Hepatitis C virus (HCV); therefore, we developed convenient sequences for synthesis of modified adenosine 5'-phosphonates in which the hydroxyl group at 2' or 3'-position of the sugar moiety is substituted with the azido or amino group and the oxymethyl group at the 4'-position is modified by the ethylene or vinyl group. This synthetic sequence can provide six adenosine 5'-phosphonates via one protocol, and is considered to be very efficient and a convenient route of synthesis. An assay of adenosine 5'-phosphonate analogues (1, 2, 3, 4, 5, and 6) against HCV infection is now in progress.

• Macromolecular Research
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• v.17 no.8
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• pp.563-567
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• 2009

In order to improve the thermomechanical performance of polyketone, a third monomer (4-methylstyrene) was added to the copolymerization system. The terpolymer of CO, styrene, and 4-methylstyrene was synthesized in the presence of multi component catalysts containing palladium acetate and rare earth metal phosphonates. The products were characterized by infrared spectroscopy (IR), and nuclear magnetic resonance spectroscopy (NMR). The effects of the different components, including the third monomer, palladium acetate, 2,2'-bipyridyl, rare earth phosphonate, p-toluene-sulphonic acid, and p-benzoquinone, were also studied. The highest catalytic activity of 965.51 g/(gPd h) was obtained with a catalyst containing palladium acetate and rare earth phosphonate.

• The Korean Journal of Pesticide Science
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• v.3 no.1
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• pp.20-28
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• 1999

Chloronicotinyl derivatives were synthesized by substitution of amino in 3-pyridylmethylamine with phosphite groups and their insecticidal and fungicidal activities were determined. At 500 ppm, compound 4 with methyl and butyl group in phosphonate and compound 5, 6, 7, and 8 with two butyl, 2,2,2-trifluorotehtyl, 2-ethylhexyl, phenyl, respectively, in phosphonate showed 90% insecticidal activities against brown plant-hopper (Nilaparvate lugens). These compounds showed, however, poor insecticidal activities against diamond-back moth (Plutella xylostella) and two-spotted spider mite (Tetranychus urticae) (<65%), suggesting that insecticidal activity of chloronicotinyl derivatives containing phosphorus moieties are species-dependent. Newly synthesized chloronicotinyl derivatives with halogen and/or heterocycle (compound $10{\sim}21$) did not show insecticidal activities. We also determined fungicidal activity of the synthesized chloronicotinyl derivatives against rice sheath blight (Pyricularia grisea), cucumber gray mold (Bortytis cinerea), tomato late blight (Phytophthora infestans), wheat leaf rust (Puccinia recondita), and barley powdery mildew (Erysiphe graminis). Compound 10 with butyl and 4-nitrophenyl in phosphonate at 10 ppm showed 85% fungicidal activity against rice blast, suggesting that chloronicotinyl derivatives containing phosphorus moieties could be developed as a fungicidal agent of a novel chemical structure.

• Bulletin of the Korean Chemical Society
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• v.25 no.9
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• pp.1326-1330
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• 2004

Several new derivatives of oxazolidinone phosphonate, that are expected to show biological activity, were prepared efficiently by previously published methods. ${\gamma}$-Ketophosphonate 1 was synthesized using pentacovalent oxaphosphorane chemistry followed by reductive amination with aromatic amine of oxazolidinone 4. Biological activity of the synthetic compounds has been studied. One of the synthetic compounds showed promising result for us to pursue further studies.

• Bulletin of the Korean Chemical Society
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• v.16 no.9
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• pp.886-891
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• 1995

Electroactive monolayers based on zirconium(Ⅳ) phosphonate film were prepared on gold and tin oxide electrodes by sequential layer-by-layer depostion technique. High transfer coefficient values and surface coverages of surface bound redox molecules were obtained from the electrochemical measurements of heterogeneous electron transfer rates for monolayer modified electrodes. 1,10-Decanediylbis(phosphonic acid) (DBPA) monolayer as insulating barrier was effective in blocking electron transfer. However, these film modified oxide electrode shows voltammetric behavior of diffusion/permeation process taking place at very small exposed area of modified electrode through channels due to structural defects within film when a very fast redox couple such as Ru(NH3)63+ is hired.

• Bulletin of the Korean Chemical Society
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• v.10 no.4
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• pp.393-394
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• 1989

• Bulletin of the Korean Chemical Society
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• v.18 no.10
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• pp.1120-1123
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• 1997

• Bulletin of the Korean Chemical Society
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• v.33 no.8
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• pp.2574-2580
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• 2012

The discovery that threosyl phosphonate nucleoside (PMDTA, $EC_{50}=2.53{\mu}M$) is a potent anti-HIV agent has led to the synthesis and biological evaluation of 5'-deoxy versions of threosyl phosphonate nucleosides. In the present study, (E)-3'-phosphonoalkenyl and 3'-phosphonoalkyl nucleoside analogues 13, 16, 20 and 23 were synthesized from acetol and tested for anti-HIV activity and cytotoxicity. The adenine analogue 16 was found to exhibit moderate in vitro anti-HIV-1 activity ($EC_{50}=22.2{\mu}M$).

• Bulletin of the Korean Chemical Society
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• v.32 no.8
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• pp.2689-2694
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• 2011

Novel 5'-norcarbocyclic adenine and guanine phosphonic acid analogues with 6'-electronegative moiety such as unsaturated C-C bond were designed and synthesized from commercially available 2-methylene-propane-1,3-diol (4). Regioselective Mitsunobu reaction successfully proceeded from an allylic functional group (${\pm}$)-12b at low reaction temperature in polar cosolvent (DMF/1,4-dioxane) to give purine phosphonate analogues (${\pm}$)-13 and (${\pm}$)-20. The purine nucleoside phosphonate and phosphonic acid analogues were subjected to antiviral screening against HIV-1. Guanine analogue (${\pm}$)-23 shows significant anti-HIV activity in PBM cell lines ($EC_{50}=8.1\;{\mu}M$).