• 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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• 제31권11호
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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.

• 대한화학회지
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• 제55권5호
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• pp.892-895
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• 2011

• 공업화학
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• 제25권5호
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• pp.481-486
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• 2014

이 연구에서는 피페라지노메틸-비스-포스폰산, 메틸피페라지노메틸-비스-포스폰산, N,N-디메틸렌디아미노메틸-비스-포스폰산으로 처리된 중밀도섬유판의 연소성을 시험하였다. 15 wt%의 알킬렌디아미노알킬-비스-포스폰산 수용액으로 중밀도섬유판에 3회 붓칠하여 실온에서 건조시킨 후, 콘칼로리미터(ISO 5660-1)를 이용하여 연소 특성을 고찰하였다. 그 결과, 알킬렌디아미노알킬-비스-포스폰산으로 처리한 시험편이 무처리 시험편과 비교하여 연소 억제성을 향상시켰다. 특히 알킬렌디아미노알킬-비스-포스폰산으로 처리한 시험편은 연소속도 감소에 의하여 무처리 시험편과 비교하여 각각 지연된 착화시간(148 s~116 s), 긴 불꽃소멸시간(633 s~ 529 s), 그리고 낮은 총열방출률($61.1MJ/m^2{\sim}67.0MJ/m^2$)을 나타내었다. 따라서 알킬렌디아미노알킬-비스-포스폰산으로 처리한 시험편은 중밀도섬유판 시험편에 비하여 낮은 연소성질을 나타내었다. 그러나 피페라지노메틸-비스-포스폰산으로 처리한 시험편은 무처리 시험편과 비교하여 높은 최대열방출률($75.7kW/m^2$)을 나타내었다.

• 통합자연과학논문집
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• 제8권1호
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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.

• 한국화재소방학회논문지
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• 제27권5호
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• pp.57-63
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• 2013

이 연구에서는 피페라지노메틸-비스-포스폰산, 메틸피페라지노메틸-비스-포스폰산, N,N-디메틸렌디아미노메틸-비스-포스폰산으로 처리된 리기다 소나무의 연소성을 시험하였다. 15 wt%의 알킬렌디아미노알킬-비스-포스폰산 수용액으로 리기다 소나무에 3회 붓칠하여 실온에서 건조시킨 후, 콘칼로리미터(ISO 5660-1)를 이용하여 그의 연소성을 시험하였다. 그 결과, 알킬렌디아미노알킬-비스-포스폰산으로 처리한 시험편은 무처리 시험편에 비하여 그의 연소 억제성을 부분적으로 증가시켰다. 특히 알킬렌디아미노알킬-비스-포스폰산으로 처리한 시험편은 연소속도 감소에 의하여 무처리 시험편에 비해 각각 지연된 착화시간(148-116 s)과 긴 불꽃소멸시간(633-529 s)을 나타내었다. 따라서 알킬렌디아미노알킬-비스-포스폰산으로 처리한 시험편은 순수 리기다 소나무 시험편에 비하여 부분적으로 낮은 연소성질을 나타내었다. 그러나 피페라지노메틸-비스-포스폰산으로 처리한 시험편은 무처리 시험편에 비해 각각 높은 최대열방출률(187.56 $kW/m^2$)과 높은 총 열방출률(75.7 $MJ/m^2$)을 나타내었다.

• 한국화재소방학회논문지
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• 제28권5호
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• pp.71-79
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• 2014

이 연구에서는 비스-디알킬아미노알킬 포스핀산(DMDAP), N,N-디메틸렌디아미노메틸-비스-포스폰산(DMDEDAP), 피페라지노메틸-비스-포스폰산(PIPEABP), 메틸피페라지노메틸-비스-포스폰산(MPIPEABP)의 화학 첨가제로 처리된 중밀도 섬유판(MDF)의 연소성을 시험하였다. 15 wt%의 화학 첨가제 수용액으로 MDF에 3회 붓칠하여 실온에서 건조시킨 후, 콘칼로리미터(ISO 5660-1), 방염성능 시험(소방방재청 고시 제 2012-34호), 휘발성 유기 화합물측정시험(KS M ISO 11890-2)을 이용하여 그의 연소성을 시험하였다. 그 결과, 비스-디메틸아미노메틸 포스피닉산과 알킬렌디아미노알킬-비스-포스폰산으로 처리한 섬유판은 연소속도 감소에 의하여 무처리한 섬유판에 비해 긴 연소시간 = (442~492) s을 나타내었다. 게다가 탄화면적과 탄화길이는 각각 $(44.33{\sim}61.33)cm^2$와 (10.33~11.67) cm로서 무처리한 시험편보다 높게 측정되었다. 또한 화학 첨가제 수용액으로 처리한 섬유판의 휘발성 유기화합물은 규정 한도내에서 (0.188~0.333) g/L으로 발생하였으며, 무처리한 시험편의 휘발성 유기화합물 보다 높게 나타났다. 따라서 비스-디알킬아미노알킬 포스폰산과 알킬렌디아미노알킬-비스-포스폰산으로 처리된 섬유판은 무처리한 섬유판보다 난연성을 부분적으로 향상시킨 것으로 판단 된다.

• Journal of Plant Biology
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• 제15권2호
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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.

• 통합자연과학논문집
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• 제8권3호
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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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• 제32권8호
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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 ($EC_{50}=8.1\;{\mu}M$).