• Title/Summary/Keyword: Phosphonic acid

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Synthesus of DL-1-Amino Alkyl Phosphonic Acids and Their Derivatives (II) (DL-1-Amino Alkyl Phosphonic Acid 와 그 유도체들의 합성 (ll))

  • Kyung Yeon Cho;Duck Chan Kim;Yong Joon Kim
    • Journal of the Korean Chemical Society
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    • v.15 no.5
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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.

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Synthesis of DL-1-Amino Alkyl Phosphonic Acids and their Derivatives (DL-1-Aminoalkyl Phosphonic Acids와 그유도체들의 합성 (I))

  • Cho Kyung Yeon;Kim Duck Chan;Kim Yong Joon
    • Journal of the Korean Chemical Society
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    • v.15 no.1
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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.

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Synthesis and Antiviral Evaluation of 1'-Branched-5'-Norcarbocyclic Adenosine Phosphonic Acid Analogues

  • Oh, Chang-Hyun;Yoo, Kyung-Ho;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.31 no.9
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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.

Solid State NMR Studies of Proton Conducting Polymer, Poly(vinyl phosphonic) acid

  • Lee, Young-Joo;Bingol Bahar;Murakhtina Tatiana;Sebastiani Daniel;Ok, Jong-Hwa;Meyer Wolfgang H.;Wegner Gerhard;Spiess Hans Wolfgang
    • Proceedings of the Polymer Society of Korea Conference
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    • 2006.10a
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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.

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Synthesis of SATE Prodrug of 6'-Fluoro-6'-methyl-5'-noradenosine Nucleoside Phosphonic Acid as a New Class of Anti-HIV Agent

  • Li, Hua;Yoo, Jin-Cheol;Baik, Young-Chan;Lee, Won-Jae;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.31 no.9
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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.

Synthesis of Alkylenediaminoalkyl-bis-Phosphonic Acid Derivatives (알킬렌디아미노알킬-비스-포스폰산 유도체의 합성)

  • Chung, Yeong-Jin;Jin, Eui
    • Journal of the Korean Applied Science and Technology
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    • v.30 no.1
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    • pp.1-8
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    • 2013
  • Four kinds of new alkylenediaminoalkyl-bis-phosphonic acid derivatives with alkylenediaminoalkyl functional groups in the molecule were synthesized and their smoke density(Ds) were tested. These alkylenediaminoalkyl-bis-phosphonic acid derivatives were prepared in yields(76-97.3%) by one step reaction of the phosphorus acid with amine and aldehyde. Smoke density was measured by the method of ASTM E 662. The values of smoke density were obtained from 234.7 to 437.9. The smoke density of compounds with two phosphonic acid structures were increased more than that of compounds with one phosphonic acid structure. In addition, there was correlation between the smoke density and the number of nitrogen atoms in amino group attached to mono- or di-phosphonic acids group.

Synthesis of Novel 2'-Spirocyclopropanoid 4'-Deoxythreosyl Phosphonic Acid Nucleoside Analogues

  • Shen, Guang Huan;Hong, Joon Hee
    • Bulletin of the Korean Chemical Society
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    • v.34 no.3
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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 ${\mu}M$.

Competitive Solvent Extraction of the Mixture of Alkali Metal and Alkaline Earth Metal Cation containing Crown Ether Carboxylic Acid and Crown Ether Phosphonic Acid (크라운에테르 카르복시산과 크라운에테르 포스포닉산을 포함한 알칼리 금속과 알칼리 토금속 양이온 혼합물의 경쟁적 용매추출)

  • Chung, Yeong-Jin
    • Journal of the Korean Applied Science and Technology
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    • v.22 no.3
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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%).

Competitive Solvent Extractions of Alkaline Earth Metal Cations by Crown Ether Phosphonic Acid Monoethyl Esters (크라운에테르 포스포닉산 모노에틸 에스테르에 의한 알칼리 토금속 양이온의 경쟁 용매추출)

  • Chung, Yeong-Jin
    • Journal of the Korean Applied Science and Technology
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    • v.22 no.1
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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 $\underline{6}$.

Synthesis and Some Properties of 4'-Phenyl-5'-Norcarbocyclic Adenosine Phosphonic Acid Analogues

  • Liu, Lian Jin;Kim, Eun-Ae;Hong, Joon-Hee
    • Bulletin of the Korean Chemical Society
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    • v.32 no.5
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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.