• Bulletin of the Korean Chemical Society
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• v.35 no.9
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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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• v.31 no.11
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• pp.3348-3352
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• 2010

Novel 4'-ethyl-5'-norcarbocyclic adenosine phosphonic acid analogues were synthesized from propionaldehyde 5 through a de novo acyclic synthetic route using reiterative Grignard additions and ring-closing metathesis (RCM) as key reactions. The synthesized nucleoside phosphonic acids analogues 17, 18, 19, and 21 were subjected to antiviral screening against human immunodeficiency virus.

• Journal of the Korean Chemical Society
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• v.55 no.5
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• pp.892-895
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• 2011

• Applied Chemistry for Engineering
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• v.25 no.5
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• pp.481-486
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• 2014

This study was performed to test combustive properties of medium density fibreboard (MDF) plates treated with piperazinomethyl-bis-phosphonic acid (PIPEABP), methylpiperazinomethyl-bis-phosphonic acid (MPIPEABP), and N,N-dimethylethylenediaminomethyl-bis-phosphonic acid (MDEDAP). MDF specimens were painted three times with 15 wt% solution of the alkylenediaminoalkyl-bis-phosphonic acids at room temperature. After drying specimen treated with chemicals, combustive properties were examined using the cone calorimeter (ISO 5660-1). As a result, combustion-retardation properties increased due to the treatment of bare MDF with alkylenediaminoalkyl-bis-phosphonic acid solution. Especially, the specimens treated with chemicals showed the ignition (TTI) (148 s~116 s) was retarded and the flameout (Tf) (633 s~529 s) time increased, while the total heat release rate (THRR) (61.1~67.0) $MJ/m^2$ was lowered than those of using virgin plate by reducing the burnig rate. Compared with virgin MDF plate, the specimens treated with the alkylenediaminoalkyl-bis-phosphonic acids showed low combustive properties. However the specimens treated with bis-(dimethylaminomethyl) phosphinic acid (DMDP) showed the higher peak heat release rate (PHRR) ($185.08kW/m^2$) than that of the virgin plate.

• Journal of Integrative Natural Science
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• v.8 no.1
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• pp.48-55
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• 2015

Novel 2'(${\beta}$)-methyl-5'-deoxyapiose purine phosphonic acid analogues were designed and synthesized from 2-propanone-1,3-diacetate. Condensation successfully proceeded from a glycosyl donor 9 under Vorbr${\ddot{u}}$ggen conditions. Condensation of aldehyde 14 with Wittig reagent [(diethoxyphosphinyl)methylidene] triphenylphosphorane gave the desired nucleoside phosphonate analogues 15. Ammonolysis and hydrolysis of phosphonates gave the nucleoside phosphonic acid analogue 17 and 19. The synthesized nucleoside analogues were subjected to antiviral screening against HIV-1. The adenine analogue 19 exhibited weak in vitro activities against HIV-1.

• Fire Science and Engineering
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• v.27 no.5
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• pp.57-63
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• 2013

This study was performed to test the combustive properties of Pinus rigida plates treated with piperazinomethyl-bisphosphonic acid (PIPEABP), methylpiperazinomethyl-bis-phosphonic acid (MPIPEABP), and N,N-dimethylethylenediaminomethyl- bis-phosphonic acid (MDEDAP). Pinus rigida specimens were painted in three times with 15 wt% alkylenediaminoalkyl- bis-phosphonic acid solutions at the room temperature. After drying specimen treated with chemicals, combustive properties were examined by the cone calorimeter (ISO 5660-1). As a result, the combustion-retardation properties were increased by due to the treated alkylenediaminoalkyl-bis-phosphonic acid solutios in the virgin Pinus rigida. Especially, the specimens treated with chemicals showed both the later time to ignition (TTI) (148-116 s) and longer time to flameout (Tf) (633-529 s) than those of virgin plate by reducing the burnig rate. Compared with virgin pinus rigida plate, the specimens treated with the alkylenediaminoalkyl-bis-phosphonic acids showed partially low combustive properties. However the specimens treated with PIPEABP showed both the higher peak heat release rate (PHRR) (187.56 $kW/m^2$) and higher total heat release rate (THRR) (75.7 $MJ/m^2$) than those of virgin plate.

• Fire Science and Engineering
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• v.28 no.5
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• pp.71-79
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• 2014

This study was performed to test the combustive properties of Medium Density Fibreboards (MDFs) treated with chemicals of the bis-(dimethylaminomethyl) phosphinic acid (DMDAP), N,N-dimethylethylenediaminomethyl-bis-phosphonic acid (DMDEDAP), piperazinomethyl-bis-phosphonic acid (PIPEABP), and methylpiperazinomethyl-bis-phosphonic acid (MPIPEABP). MDFs were painted in three times with 15 wt% solution of the bis-(dimethylaminomethyl) phosphinic acid and alkylenediaminoalkyl-bis-phosphonic acids at the room temperature, respectively. After drying MDF treated with chemicals, combustive properties and volatile organic compounds (VOCs) contents were examined by the cone calorimeter (ISO 5660-1), test for flame retardant (NEMA Notice No. 2012034), and gas chromatography (KS M ISO 11890-2), respectively. It was indicated that the MDFs treated with chemicals showed the longer time to combustion time (CT) = (442~492) s than that of virgin plate by reducing the burning rate except for CT treated with DMDAP. In adition, the MDFs treated with chemicals showed both of the higher char area (44.33~61.33) kg/kg and char length (10.33~11.67) cm than those of virgin plate. Especially, the MDFs treated with chemicals showed the higher mean volatile organic compounds (VOCs) (0.188~0.333) g/L than that of virgin plate within the prescribed limits. Thus, It is supposed that the combustion- retardation properties were improved by the partial due to the treated chemicals in the virgin MDF.

• Journal of Plant Biology
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• v.15 no.2
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• pp.1-6
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• 1972

Cultivar Yeollow Special A, the most leading Korean economic leaf tobacco in Korea, were field-cultivated in four different localities of Korea for the period of two years (1970 and 1971) and sprayed at varied levels of 2-chloroethyl phosphonic acid (CEPA) for foliar application few days after topping. While no striking difference in leaf yield by weight was obtained among the treatments when compared with control, leaf quality as expressed for shipment price in won tended when compared with control, leaf quality as expressed for shipment price in won tended to improve. The treated leaves with 300 to 900 ppm of CEPA (approximately 140 1/acre of 500 ppm) not only showed yellowing and accelerated maturity to pick 4 to 5 days with practicable optimal level earlier than control, but also speeded up to take nearly with practicable optimal level earlier than control, but also speeded up to take nearly last half of the total time required for the five stages of flue-curing. It is therefore considered that CEPA is as effective maturity-accelerating agent and useful as known for other solanaceous plants showing climacteric stage respiration, and discussions were made about physiological actions of ethylene gas released from CEPA at plant tissues sprayed.

• 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.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 ($EC_{50}=8.1\;{\mu}M$).