• Journal of the Korean Chemical Society
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• v.27 no.4
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• pp.294-301
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• 1983

Six new compounds of p-acetamidobenzenesulfonamides which contain O, O'-diethyl-1-aminobenzylphosphonate and their derivatives were prepared: O, O'-diethyl N-(p-acetamidobenzenesulfonyl) aminobenzylphosphonate, N-(p-acetamidobenzenesulfonyl) aminobenzylphosphonic acid, O,O'-diethyl N-[N-(p-acetamidobenzenesulfonyl) glycyl] aminobenzylphosphonate, O,O'-diethyl N-[N-(p-acetamidobenzenesulfonyl)-DL-alanyl] aminobenzylphosphonate, O,O'-diethyl N-[N-(p-acetamidobenzenesulfonyl)-L-leucyl] aminobenzylphosphonate, and O,O'-diethyl N-[N-(p-acetamidobenzenesulfonyl)-L-phenylalanyl]aminobenzylphosphonate. All the compounds were obtained as white crystals and characterized by means of elemental analysis and infrared spectroscopy.

• Journal of the Korean Chemical Society
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• v.19 no.3
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• pp.169-173
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• 1975

Ten previously unreported dipeptides ontaining aminobenzylphosphonic acid were prepared by carbodiimide method. These are; Glycyl-dl-1-aminobenzylphosphonic acid, alanyl-dl-1-aminobenzylphosphonic acid, L-alanyl-dl-1-aminobenzylphosphonic acid, N-phthalyl-L-phenylalanyl-dl-1-aminobenzylphosphonic acid diethyl ester, N-carbobenzoxyglycyl-dl-1-aminobenzylphosphonic acid diethyl ester, N-carbobenzoxyalanyl-dl-1-aminobenzylphosphonic acid diethyl ester, N-carbobenzoxy-L-alanyl-dl-1-aminobenzylphosphonic acid diethyl ester, glycyl-dl-1-aminobenzylphosphonic acid diethyl ester hydrobromide, alanyl-dl-1-aminobenzylphosphonic acid diethyl ester hydrobromide and L-alanyl-dl-1-aminobenzylphosphonic acid diethyl ester hydrobromide. The first six compounds were characterized, and the last four compounds were obtained in the crude state.

• Bulletin of the Korean Chemical Society
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• v.4 no.4
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• pp.171-175
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• 1983

This paper reports new phosphonamide derivatives which contain diethyl aminomethylphosphonate, diethyl DL-1-aminobenzylphosphonate and 6-aminopenicillanic acid; N-(ethyl phthalimidomethylphosphonyl)-L-methionine methyl ester, N-(ethyl phthalimidomethylphosphonyl)-L-valine ethyl ester, N-[ethyl N-(methoxycarbonylmethyl)benzylphosphonamido]-2-phthalimidoacetamide, N-[ethyl N-(diethyl phosphonylbenzyl)methylphthalamido] phthalimide, N-[ethyl {ethyl N-(diethyl phosphonylbenzyl)aminomethylphosphonamido} phosphonylmethyl] phthalimide, N-[ethyl N-(diethyl phosphonylbenzyl)methylphosphonamido]-2-phthalimidoacetamide, N, N'-bis (ethyl phthalimidomethylphosphonyl)ethylene diamine, 6-(ethyl DL-1-aminobenzylphosphonamido) penicillanic acid, ethyl N-(ethoxycarbonylmethyl)-1-aminobenzylphosphonamide, ethyl N-(diethyl phosphonylbenzyl)aminomethylphosphonamide and N,N'-bis (ethyl aminomethylphosphonyl) ethylene diamine.

• Journal of the Korean Chemical Society
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• v.37 no.1
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• pp.136-140
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• 1993

New synthetic method for diethyl N-[4-{[(2,4-diamino-6-yl)methyl]-amino}benzoyl]-L-glutamate(10) which is an intermediate of methotrexate is described. p-Nitrobenzoyl-L-glutamate was obtained via a two-step sequence which involves condensation of p-nitrobenzoyl chloride with diethyl-L-glutamate and Fischer esterification reaction with ethanol. Reductive methylation of diethyl-p-nitrobenzoyl-L-glutamate were carried out by reaction with formic acid and paraformaldehyde in the presence of $PtO_2$ catalyst and yielded diethyl N-(4-methylaminobenzoyl)-L-glutamate(7). It was followed by allylation and iodoazidozation to give the diethyl-p-[N-(2-azido-3-iodopropyl)-N-methyl]aminobenzoyl-L-glutamate(9). The cyclization reaction of compound(9) with 2,4,5,6-tetraaminopyrimidine was carried out by intermolecular nucleophilic substitution to give the desired methotrexate diethylester.

• Applied Biological Chemistry
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• v.27 no.2
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• pp.64-72
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• 1984

Alachlor, 2-chloro-2, '6'-diethyl-N-(methoxymethyl) acetanilide, which had been incubated in the flooded paddy soils yielded 1-formyl-2,3-dihydro-7-ethylindole, 2,6-diethylaniline, 2,6-diethylacetanilide, 2,6-diethyl-N-(methoxymethyl) acetanilide, 2-hydroxy-2, '6'-diethyl-N-(methoxymethyl) acetanilide, and three unidentifiable compounds as its degradation products. The water-soluble products of Alachlor in soil suspensions increased with incubation periods and similar results were obtained from the incubation of Rhizoctonia solani, as verified by use of the ring $-^{14}C-$labeled Alachlor. Streptomyces lavendulae Ru 3340-8 produced 2-hydroxy-2, '6'-diethyl-N-(methoxymethyl) acetanilide as the major degradation product as much as 25%, whereas Bacillus brevis IFO 3331, Bacillus cruciviae, and Pseudomonas putida did not produce it.

• The Korean Journal of Food And Nutrition
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• v.14 no.1
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• pp.20-27
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• 2001

The consumption of radish ( Rhaphanus sativus L.) sprout, which is Cruciferae family, is increasing because of its pungent flavor and taste. Its volatile components were analyzed by SDE (simultaneous steam distillation & extraction) method and P&T(purge & cryogenic trapping) method. As a solvent, diethyl ether and diethyl ether : pentane mixture(2:1, v/v) were used in SDE method, and diethyl ether in P&T method. Analyzing by GC and GC-MS, the major component was sulfur compounds (19 species, peak area 76.6%) with diethyl ether, sulfur compounds(15. 44.0%) and hydrocarbons(23, 23.8%) with diethyl ether-pentane mixture in SDE method. Also, hydrocarbons(25, 84.1% ) was major component in P& T method. The major volatile component of fresh radish sprout were n-heptane, methyl pentane and that of boiled radish sprout were 4-methylthio-3-butenyl isothiocyanate, methyl mercaptane, 2,3-dimethyl disulfide. Low molecular volatile components were detected more by P& T method, but types and relative quantities of volatile components were measured less comparing to SDE method.

• Korean Journal of Environmental Agriculture
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• v.3 no.1
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• pp.1-9
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• 1984

Two of the degradation products of alachlor in soil. product 1, 2,6-diethyl-N-(methoxymethyl) acetanilide and product 2,2-hydroxy-2',6'-diethyl-(methoxymethyl) acetanilide were synthesized from alachlor reacting with 3N-hydrochloric acid in the presence of zinc powder at room temperature and a saturated sodium bicarbonate solution at $90^{\circ}C$ for 78 hr, respectively. At the concentrations of both $5{\times}10^{-4}M\;and\;1{\times}10^{-3}M$, product 2 exhibited almost the same phytotoxicity to rice seedlings, in particular, as alachlor, whereas product 1 lost its phytotoxic effectiveness. It seems that substitution of chlorine atom by hydroxyl group did not affect the phytotoxicity of alachlor, whereas substitution by hydrogen atom did.

• Microbiology and Biotechnology Letters
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• v.24 no.5
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• pp.624-629
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• 1996

The ethanol extracts from Angelica gigas Nakai and Angelica acutiloba Kitagawa were fractionated to diethyl ether and aqueous partitions. Both partitions had strong antimutagenic effect on the MNNG (N-methyl-N-nitro-N-nitrosoguanidine) by Ames mutagenicity test. Diethyl ether fractions exhibited the greatest antimutagenic effect suppressing the mutagenicity of MNNG with inhibition of 78-80%. The ethanol extracts from both species showed the inhibitory effect on the growth of several human cancer cell lines. Especially, the diethyl ether fraction from ethanol extracts was most effective on human hepatocellular carcinoma cells, inhibiting 90-95% of cell growth. However, the aqueous fractions had least inhibition activity on many cancer cells. There was little cytotoxicity on human normal liver cell by ethanol extracts. Diethyl ether fraction from Angelica gigas Nakai ethanol extract had cytotoxicity less than 20% on human normal liver cells, compared with that from Angelica acutiloba Kitagawa ethanol exract. The adding of 0.5 (g/l) of diethyl ether fractions of Angelica gigas Nakai or Angelica acutiloba Kitagawa increased immune activity by enhacing human B and T cells up to three to four times. It was proven that diethyl ether fraction (0.7 g/1) from Angelica gigas Nakai could control blood pressure by suppressing angiotensin converting enzyme activity up to 98%. From TLC, it was appeared that both of diethyl ether partitions had umbelliferon, known to one of active substances from Angelica gigas Nakai and Angelica acutiloba Kitagawa.

• Journal of the Korean Chemical Society
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• v.43 no.1
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• pp.85-91
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• 1999

The second order rate constants for the hydrolysis of substituted phenyl N,N-diethyl-P-benzylphosphonamidates (2,4-$(NO_2)_2$, 4-$NO_2$, 4-CN, 4-Cl, 4-H)in 20% dioxane-water (v/v) have been determined by UV/Vis spectrophotometric method at various temperatures. The activation parameters (Ea, ${\Delta}H^{\neq}$,${\Delta}S^{\neq}$) were calculated from the rate constants and the reaction constant ($\rho$) was also estimated by Hammett equation. The activation entropies of the title reactions show considerably negative values, this result is not consistent with a dissociative mechanism (EA) in which a positive or a slightly negative value of the entropy of activation should be expected. Further, kinetic evidence for an associative mechanism (AE) was obtained from the linear free energy relationship. By the results of kinetic study for the alkaline hydrolysis of substituted phenyl N,N-diethyl-P-benzylphosphonamidates, it may be concluded that these reactions proceed through an associative mechanism.

• Applied Biological Chemistry
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• v.29 no.2
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• pp.182-189
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• 1986

Alachlor, 2-chloro-2',6'-diethyl-N-(methoxymethyl) acetanilide produced four major degradation products, when incubated under an upland soil condition for 80 days. They include 8-ethyl-2-hydroxy-N-(methoxymethyl)-1,2,3,4-tetrahydroquinoline (m/z 221), N-hydroxyacetyl-2,3-dihydro-7-ethylindole (m/z 205), 2-hydroxy-2',6'-diethyl-N-(methoxymethyl) acetanilide (m/z 251), and 9-ethyl-1,5-dihydrol-(methoxymethyl)-5-methyl-4,1-benzoxazepin-2 (3H)-one (m/z 249). The products turned out to be a little different from those obtained under the flooded paddy soil condition used in the previous paper. The plausible pathways for the degradation were proposed.