• 대한화학회지
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• 제15권5호
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• pp.275-280
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• 1971

Six previously unreported N-acylated-DL-1-amino alkyl phosphonic acids were prepared; N-Acetyl-DL-1-amino-3-methyl butyl phosphonic acidN-Benzoyl-DL-1-amino-2-methyl propyl phosphonic acidN-Benzoyl-DL-1-amino-3-methyl butyl phosphonic acidN-Benzoyl-DL-1-amino-2-methyl butyl phosphonic acidN-Acetyl-DL-1-amino-2-methyl propyl phosphonic acidN-Acetyl-DL-1-amino-2-methyl butyl phosphonic acidThe first four compounds were characterized, and the last two compounds were obtained in the crude oil state. The above three DL-1-amino-alkyl phosphonic acid were synthesized from iso-valeric acid, iso-caproic acid and ${\beta}$-methyl valeric acid using Hell-Volhard-Zelinsky reaction, the condensation reaction with triethyl-phosphite and the modified Curtius Reaction. Iso-caproic acid and ${\beta$-methyl valeric acid were prepared by the conventional methods.

• 대한화학회지
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• 제15권1호
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• pp.15-22
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• 1971

DL-1-Amino-pentyl phosphonic acid, DL-1-Aminopropyl phosphonic acid were synthesized with good yield from caproic acid and butyric acid using the modified Curtius reaction and N-derivatives, N-acetyl-DL-1-amino propyl phosphonic acid, N-acetyl-DL-1-aminopentyl phosphonic acid, N-Benzoyl-DL-1-amino-propyl phosphonic acid, were also prepared by a variety of methods including the Schotten-Baumann reaction. In addition, the chemical and physical properties of the products were investigated. All the products were also identified by means of elemental analysis, Infrared spectrophotometry, Ninhydrin test, and the determination of the neuralization equivalent.

• Bulletin of the Korean Chemical Society
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• 제31권9호
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• pp.2473-2478
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• 2010

Novel 1'-methyl-5'-norcarbocyclic adenosine phosphonic acid analogues were synthesized using an acyclic stereoselective route from commercially available 3,3-diethoxy-propan-1-ol 4. The synthesized nucleoside phosphonate 19 and phosphonic acid 21 were subjected to antiviral screening against various viruses.

• 한국고분자학회:학술대회논문집
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• 한국고분자학회 2006년도 IUPAC International Symposium on Advanced Polymers for Emerging Technologies
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• pp.347-347
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• 2006

Polymers containing poly(vinyl phosphonic) acid segments are promising candidates to be used as proton conducting membranes. Solid state NMR spectroscopy represents an ideal probe of proton motion on the molecular level, because it allows us to selectively detect the nuclei of interest. In this paper, we apply solid state NMR methods to poly(vinyl phosphonic) acid in order to demonstrate that the proton conduction of poly(vinyl phosphonic acid) results from P-OH proton through hydrogen bonding and that the condensation of phosphonic acid leads to decrease in proton conductivity. $^{1}H\;and\;^{31}P$ solid state NMR experiments are supported by quantum chemical computation of NMR parameters.

• Bulletin of the Korean Chemical Society
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• 제31권9호
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• pp.2514-2518
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• 2010

A very simple synthetic route of a novel SATE prodrug type of 6'-fluoro-6'-methyl-5'-noradeonosine carbocyclic nucleoside phosphonic acid is described. The key fluorinated alcohol intermediate 7 was prepared from the epoxide intermediate 6a via selective ring-opening of epoxide. Coupling of 7 with $N^6$-bis-Boc-adenine under a Mitsunobu reaction followed by phosphonation and deprotection afforded the carbocyclic phosphonic acid. The chemical stability of the bis(SATE) derivative 13 was measured at neutral (pH 7.2) and slightly acidic (Milli-Q water, pH 5.5) pH. The antiviral activity test of the SATE prodrug 13 and its parent nucleoside phosphonic acid 11 were evaluated against HIV-1.

• 한국응용과학기술학회지
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• 제30권1호
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• pp.1-8
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• 2013

알킬렌디아미노 기능기를 분자 내에 갖는 4종의 새로운 알킬렌디아미노알킬-비스-포스폰산 유도체들을 합성하고, 그들의 연기밀도를 측정하였다. 이 화합물들은 알킬렌디아민 및 알데히드에 인산을 첨가하여 한 단계로 반응시켜 2개의 인산에 2개의 아미노기를 갖는 화합물로서 76~97.3%의 수율을 얻었다. 이들의 연기밀도 시험은 ASTM E 662의 방법으로 측정하였으며, 시험결과 연기밀도(Ds)값이 234.7~437.9으로 측정되었고, 2개의 인산을 갖는 화합물이 1개의 인산구조를 갖는 화합물보다 연기밀도가 증가되었다. 따라서 하나 또는 두 개의 인산에 결합된 아마노기의 질소수와 연기밀도 사이에는 관련이 있었다.

• Bulletin of the Korean Chemical Society
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• 제34권3호
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• pp.868-874
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• 2013

Efficient synthetic route to novel 2'-spirocyclopropanoid 4'-deoxythreosyl phosphonic acid nucleosides was described from 1,4-dihydroxy-2-butene. Cyclopropane moiety was prepared via ester enolate alkylation using (2-chloroethyl)dimethylsulfonium iodide. Synthesized nucleoside analogues 16, 19, 23 and 26 were tested for anti-HIV activity as well as cytotoxicity. However, none of them showed any anti-HIV activity or cytotoxicity up to 100 ${\mu}M$.

• 한국응용과학기술학회지
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• 제22권3호
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• pp.219-227
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• 2005

Competitive solvent extraction of the mixure of alkali metal and alkaline earth cation from water into organic solvent containing the crown ether carboxylic acid and anlogous crown ether phosphonic acid was investigated as follows. The lipophilic group is found to strongly influence to the selective extraction in the mixed systems from only alkali metal cation for sym-(n-decyldibenzo)-16-crown-5-oxyacetic acid $\underline{1}$ to mostly alkaline earth metal cation for sym-bis[4(5)-tert-butylbenzo]-16-crown-5-oxyacetic acid $\underline{3}$. Monoethyl sym-(n-decyldibenzo)-16-crown-5-oxymethylphosphonic acid $\underline{2}$. and monoethyl-sym- bis]4(5)-tert-butylbenzo]-16-crown-5-oxymethylphosphonic acid $\underline{4}$ showed good selectivity for $Na^+$ over $Mg^{2+}$, the second extracted ion. Structural variation in the crown ether phosphonic acid somewhat was influenced to the extraction selectivity in the mixed systems. when variation of the ionized group is influenced in the mixed systems, the selectivity of $Na^+$ as the second extracted ion was much better crown ether carboxylic acid $\underline{1}$ than crown ether phosphonic acid $\underline{2}$, while the efficiency of $Na^+$ extraction was better $\underline{2}$ (83% total loading) than $\underline{1}$ (32%).

• 한국응용과학기술학회지
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• 제22권1호
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• pp.9-14
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• 2005

Competitive solvent extraction of alkaline earth metal cations from water into organic solvent containing the carboxylic acid crown ether and analogous crown ether phosphonic acid monoethyl esters were investigated. sym-(n-Decyldibenzo)-16-crown-5xyacetic acid $\underline{1}$ and monoethyl sym-(n-decyldibenzo)-16-crown-5-oxymethylphosphonic acid $\underline{3}$ are structurally identical except for the ionizable groups. Both of them provide similar extraction behavior in terms of efficiency and selectivity, but monoethyl sym-(n-decyldibenzo)-16-crown-5-oxymethylphosphonic acid $\underline{3}$ showed higher alkaline earth metals loadings at acidic or neutral media. Monoethylsym-(n-octyldibenzo)-16-rown-5-oxymethylphosphonic acid $\underline{2}$ showed better selectivity and alkaline earth metals loading than did the analogous sym-(n-octyldibenzo)-16-crown-5-oxymethyldiphosphonic acid $\underline{6}$.

• Bulletin of the Korean Chemical Society
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• 제32권5호
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• pp.1662-1668
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• 2011

Steric and electronic parameters of 4'-substituents play significant roles in steering the conformation of nucleoside analogues. In order to investigate the relationship of 4'-substituent with antiviral enhancement, novel 4'-phenyl-5'-norcarbocyclic adenosine phosphonic acid analogues were racemically synthesized via de novo acyclic stereoselective route from propionaldehyde 5. The phenyl substituted cyclopentenols 15a and 15b as key intermediates were successfully constructed via reiterative carbonyl addition of Grignard reagents and ring-closing metathesis of corresponding divinyl 14. The synthesized nucleoside phosphonic acids analogues 19, 20, 21, and 23 were subjected to antiviral screening against HIV-1.