• Title/Summary/Keyword: Oxime

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Synthesis of 6-amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan (6-Amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan의 합성)

  • Kim, Min-Kyeom;Ma, Eun-Sook
    • YAKHAK HOEJI
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    • v.52 no.1
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    • pp.20-26
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    • 2008
  • 2-Aminothiazole ring as a bioisoster of catechol in dopamine has provided with good oral availability and lipophilic property. Selenium was reported to have an improved antioxidant ability and to reduce the loss of dopamine. 2-Aminoindan, is a rigid form of dopamine, was evaluated as a dopamine agonist with low neurotoxocity. In order to develop a novel dopamine agonist, we tried to synthesize the selenazoloaminoindan derivative that is a hybrid structure of aminoindan and aminoselenazole instead of aminothiazole. 2-Indanone-2-oxime was reduced with $TiCl_4$ and $NaBH_4$ to form 2-aminoindan, which was reacted with propionyl chloride to give 2-N-n-propionylaminoindan (2). Compound 2 was reduced with $TiCl_4$ and $NaBH_4$ to afford 2-N-n-propylaminoindan (3) and it was nitrated and reduced to form 5-amino-2-N-n-propylaminoindan (5), which was reacted with KSeCN, $Br_2$, and glacial acetic acid to give 4,6-dibromo-5- amino-2-N-n-propylaminoindan (7) instead of selenazole ring formation. Otherwise, compound 2 was nitrated and hydrogenated to form 5-amino-2-N-n-propionylaminoindan (9), which was treated with KSeCN, $Br_2$, and glacial acetic acid to give 4,6-dibromo-5-amino-2-N-n-propionylaminoindan (10). Compound 9 was cyc1ized with KSeCN and glacial acetic acid in the absence of $Br_2$ to give 6-amino-2-N-(n-propionylamino)selenazolo[4,5-f]indan (11).

Reduction of Local Body Fat Thickness and Stimulation of Fat Cell Lipolysis by Slim813 (Slim813의 지방산 분해 촉진을 통한 슬리밍 효능 연구)

  • Park, Mi-Young;Jung, Kyoung-Mi;Joo, Kyoung-Mi;Kim, Yeon-Joon;Park, Young-Ho;Lim, Kyung-Min
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.38 no.2
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    • pp.189-195
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    • 2012
  • Slim813 is a 2-cyclopentene-1-one oxime derivative with potent anti-inflammatory and anti-photoaging effects. Slim813 inhibited LPS-induced TNF-${\alpha}$ production and attenuated UVB-induced MMP1 expression. Here in an attempt to find an unrevealed efficacy of Slim813, we found that Slim813 stimulates lipolysis in a dose-dependent manner by increasing intracellular cAMP level through the elevation of HSL activity in fully differentiated adipocytes. Moreover, topical application of Slim813 for two weeks in human reduced the thickness of subcutaneous fat in arm and thigh regions, implying it could be effectively used in the reduction of unwanted local fat accumulation.

Recovery of Palladium from a Mixture of Pt, Pd and Rh by Solvent Extraction

  • Kim, berly S. Svalstad;Kim, Nam-Soo;Kenneth N. Han
    • Proceedings of the IEEK Conference
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    • 2001.10a
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    • pp.482-488
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    • 2001
  • Platinum group metals (pgm) are useful to many industries such as chemical, dental and medical, petroleum, refining, electrical and electronic, and automotive. Researchers at the South Dakota School of Mines and Technology and PGM Recovery Ltd. have developed jointly an environmentally sound and metallurgically efficient process for extracting these metals from secondary sources. Once these metals have been dissolved in the leach liquor, the individual metals mainly platinum, palladium, and rhodium, should be separated in order to recover the individual metals with high purity. During this investigation, solvent extraction has been chosen as the method used to achieve the separation and extraction of platinum, palladium, and rhodium from the leach liquor. There were three solutions used throughout this procedure: 1) Synthetic solution (200 ppm Pt 80 ppm Pd 20 ppm Rh; 300 ppm Pt, 180 ppm Pd 50 ppm Rh), and 2) Auto catalyst leach liquors (100 ppm Pt, 30 ppm Pd, 20 ppm Rh). The solvents investigated included Lix 84(2-hydroxy-5-nonylacetonphenone oxime in a mixture with 5-dodecylsalicyloxime), Lix 84-I, ACORGA CLX-50 (diester of pyridine 3,5 dicarboxylic acid), and di-hexyl sulfide. The extraction values achieved using ACORGA CLX-50, Lix 84, and Lix 84-I were respectively Pt (25%, 0% 0%), Pd (100%, 99.8%, 95.3%), and Rh (99.1%, 35.5%, 4.25%). The stripping processes for the Lix 84, and Lix 84-I were proven to be more involved than others. The solutions were required to be simultaneously heated and stirred. The percentages acquired through these processes yielded unsatisfactory results. The stripping procedure for the ACORGA CLX-50 was easier to execute, yet the percentage recovered from this process was also unsatisfactory. Overall the di-hexyl sulfide has proved to be the most successful organic for this procedure. The average percent extracted for palladium was excellent with 99.9% - 100% with very little Platinum and rhodium extracted. The ability of stripping palladium in ammonia solution was also found to be excellent.

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Sageretia thea fruit extracts rich in methyl linoleate and methyl linolenate downregulate melanogenesis via the Akt/GSK3β signaling pathway

  • Ko, Gyeong-A;Shrestha, Sabina;Cho, Somi Kim
    • Nutrition Research and Practice
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    • v.12 no.1
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    • pp.3-12
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    • 2018
  • BACKGROUND/OBJECTIVES: Sageretia thea is traditionally used as a medicinal herb to treat various diseases, including skin disorders, in China and Korea. This study evaluated the inhibitory effect of Sageretia thea fruit on melanogenesis and its underlying mechanisms in B16F10 mouse melanoma cells. The active chemical compounds in anti-melanogenesis were determined in Sageretia thea. MATERIALS/METHODS: Solvent fractions from the crude extract were investigated for anti-melanogenic activities. These activities and the mechanism of anti-melanogenesis in B16F10 cells were examined by determining melanin content and tyrosinase activity, and by performing western blotting. RESULTS: The n-hexane fraction of Sageretia thea fruit (HFSF) exhibited significant anti-melanogenic activity among the various solvent fractions without reducing viability of B16F10 cells. The HFSF suppressed the expression of tyrosinase and tyrosinase-related protein 1 (TRP1). The reduction of microphthalmia-associated transcription factor (MITF) expression by the HFSF was mediated by the Akt/glycogen synthase kinase 3 beta ($GSK3{\beta}$) signaling pathway, which promotes the reduction of ${\beta}-catenin$. Treatment with the $GSK3{\beta}$ inhibitor 6-bromoindirubin-3'-oxime (BIO) restored HFSF-induced inhibition of MITF expression. The HFSF bioactive constituents responsible for anti-melanogenic activity were identified by bioassay-guided fractionation and gas chromatography-mass spectrometry analysis as methyl linoleate and methyl linolenate. CONCLUSIONS: These results indicate that HFSF and its constituents, methyl linoleate and methyl linolenate, could be used as whitening agents in cosmetics and have potential for treating hyperpigmentation disorders in the clinic.

Development of ELISA for cortisol and it's application to clinical use (ELISA를 이용한 cortisol 측정법의 정립 및 임상적 응용)

  • Na, Ki-jeong;Lee, Chang-woo
    • Korean Journal of Veterinary Research
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    • v.36 no.3
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    • pp.731-741
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    • 1996
  • ELISA kit for cortisol was developed and then evaluated. Polyclonal antihydrocortisone-3-(o-carboxymethyl)oxime BSA rabbit serum was used to coat the 96-well microplates. The minimum detection limit of the kit was 250pg of cortisol per milliliter. The within-run variation and the day to day variation of the ELISA system were 2.0 and 5.9 at maximum, respectively. The kit was used to determine whether salivary cortisol concentration could replace blood cortisol concentration in dexamathasone suppression test of dogs. Changes of cortisol concentration were measured in serum or saliva after intravenous administration of 0.01mg of dexamethasone per kilogram of body weight. Blood alone, saliva alone or both were collected at 0, 30, 60, 120, 240, and 360 minutes after injection of dexamethasone. The change in blood cortisol concentration was found to be suitable in dexamathasone suppression test of dogs, but the change in salivary cortisol concentration was not. The kit was also used to determine whether salivary cortisol concentration could be a stress index as well as blood cortisol concentration in dogs. Two types of trial were performed to estimate the stress either by blood or salivary cortisol concentration. The first trial was stress experiment by intravenous injection of 0.2IU of PZI-insulin per kilogram body weight. Either blood alone or saliva alone was collected at 0, 30, 60, and 90 minutes after insulin administration. Both blood and salivary cortisol concentration were found to be suitable index in estimating stress from hypoglycemia by injection of insulin. The second trial was stress experiment by electrical irritation. The dogs were irritated with anti-bark device for 10 seconds. Blood was collected before and at 2 and 5 minutes after electrical irritation. Saliva was collected before and at 3 and 6 minutes after electrical irritation. The blood cortisol concentration, but not the salivary cortisol concentration was found to be suitable index in estimating stress from electrical irritation. Cushing syndrome in a dog was also successfully diagnosed with this kit.

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Cecocolic Intussusception Caused by Ancylostoma caninum Infection in a Dog

  • Ko, Hui-Yeon;Kim, Joonyoung;Geum, Migyeong;Suh, Guk-Hyun;Shin, SungShik;Kim, Ha-Jung
    • Journal of Veterinary Clinics
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    • v.37 no.2
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    • pp.106-108
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    • 2020
  • An eight-month-old, outdoor, intact male English Pointer dog weighing 23.5 kg presented to the hospital with signs of hematochezia, soft stools, and weight-loss. There were no remarkable findings on physical examination, complete blood count, serum biochemistry, electrolyte and gas analysis, and radiography. The serologic and Polymerase Chain Reaction (PCR) tests for canine parvovirus were negative. A fecal smear examination showed rod-shaped, sporeforming bacteria. Additionally, a fecal flotation test showed ova of Ancylostoma spp. The size of ova was 60 × 40 ㎛, and it was identified as Ancylostoma caninum using light microscopy. The PCR test indicated a Clostridial perfringens infection and the presence of C. perfringens alpha toxin. The diagnosis given was C. perfringens enterotoxicosis with ancylostomiasis. Treatment included antibiotics (metronidazole, trimethoprim-sulfamethoxazole) and anthelmintics (afoxolaner, milbemycin oxime). After two weeks, the clostridial infection resolved, but ancylostomiasis persisted for six weeks. The anthelmintic was changed to Drontalâ plus (praziquantel/pyrantel pamoate/febantel). After four weeks, there were no remarkable findings in the fecal samples, but the patient still presented with watery stools and hematochezia. Survey of abdominal ultrasound had performed, and a target-like sign with multiple rings was seen in the cecocolic region. The patient was diagnosed with A. caninum-induced cecocolic intussusception from the history and clinical signs. After a surgery, he recovered fully. This is the first clinical case report of Ancylostoma caninum parasitizing from the small intestine and causing an intussusception in the large intestine.

Selective Reduction with Lithium Borohydride. Reaction of Lithium Borohydride with Selected Organic Compounds Containing Representative Functional Groups (수소화붕소리튬에 의한 선택환원. 수소화붕소리튬과 대표적 유기화합물과의 반응)

  • Nung Min Yoon;Jin Soon Cha
    • Journal of the Korean Chemical Society
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    • v.21 no.2
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    • pp.108-120
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    • 1977
  • The approximate rates and stoichiometries of the reaction of lithium borohydride, with fifty two selected organic compounds containing representative functional groups under the standard condition (tetrahydrofuran, $0^{\circ}$), were studied.Among the active hydrogen compounds,primary alcohols and compounds containing an acidic proton liberated hydrogen relatively fast, but secondary and tertiary alcohols very sluggishly. All the carbonyl compounds examined were reduced rapidly within one hour. Especially, among the ${\alpha}{\beta}$-unsaturated carbonyl compounds tested, the aldehydes consumed one hydride cleanly, however the cyclic ketones consumed more than one hydride even at $-20^{\circ}$. Carboxylic acids were reduced very slowly, showing about 60% reduction in 6 days at $25^{\circ}$, however acyl chlorides reduced immediately within 30 minutes. On the other hand, the reductions of cyclic anhydrides proceeded moderately to the hydroxy acid stage, however the further reductions were very slow. Aromatic and aliphatic esters, with exception of the relatively moderate reduction of acetate, were reduced very slowly, however lactones were reduced at a moderate rate. Epoxides reacted slowly, but amides and nitriles as well as the nitro compounds were all inert to this reagent. And cyclohexanone oxime and phenyl isocyanate were reduced very sluggishly. Last of all, all sulfur compounds studied were inert to this hydride.

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Reaction of Representative Organic Compounds with Sodium Borohydride in the Presence of Aluminum Chloride (염화알루미늄 존재하에서의 수소화붕소나트륨과 대표적 유기화합물과의 반응)

  • Yoon Nung Min;Ho Jun Leeq;Jin Soon Chung
    • Journal of the Korean Chemical Society
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    • v.17 no.4
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    • pp.275-285
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    • 1973
  • The addition of one mole of aluminum chloride to three moles of sodium borohydride in tetrahydrofuran gives a turbid solution with enormously more powerful reducing properties than those of sodium borohydride itself. The reducing properties of this reagent were tested with 49 organic compounds which have representative functional groups. Alcohols liberated hydrogen immediately but showed no sign of hydrogenolysis of alkoxy group. Aldehydes and ketones were reduced rapidly within one hr. Acyl derivatives were reduced moderately, however, carboxylic acids were reduced much more slowly. Esters, lactones and epoxides were reduced readily than sodium borohydride or borane. Tertiary amide was reduced slowly, however, primary amide consumed one hydride for hydrogen evolution but reduction was sluggish. Aromatic nitrile was reduced much more readily than aliphatic nitrile. Nitro compounds were inert to this reagent but azo and azoxy groups were slowly attacked. Oxime was reduced slowly but isocyanate was only partially reduced. Disulfide and sulfoxide were attacked slowly but sulfide and sulfone were inert. Olefin was hydroborated rapidly.

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Reaction of Lithium n-Butylborohydride with Selected Organic Compounds Containing Representative Functional Groups

  • Chong-Suh Pyun;Jong-Chan Son;Nung-Min Yoon
    • Bulletin of the Korean Chemical Society
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    • v.4 no.1
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    • pp.3-9
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    • 1983
  • Lithium n-butylborohydride was prepared from borane-dimethylsulfide (BMS) and n-butyllithium, and the approximate rates and stoichiometrics of its reactions with selected organic compounds containing representative functional groups were studied in THF at room temperature. Phenol and benzenetiol liberated hydrogen quickly and quantitatively, and the reactions of primary alcohols, 2,6-di-ter-butylphenol and 1-hexanethiol liberated hydrogen quantitatively within 3 hrs, whereas the reactions of secondary and tertiary alcohols were very slow. Aldehydes and ketones were reduced rapidly and quantitatively to the corresponding alcohols. Cinnamaldehyde utilized 1 equiv. of hydride rapidly, suggesting the reduction to cinnamyl alcohol. Carboxylic acids evolved 1 equiv. of hydrogen rapidly and further reduction was not observed. Anhydrides utilized 2 equiv. of hydride rapidly but further hydride uptake was very slow, showing a half reduction. Acid chlorides were reduced to the alcohol stage very rapidly. All the esters examined were reduced to the corresponding alcohol rapidly. Lactones were also reduced rapidly. Expoxides took up 1 equiv. of hydride at a moderate rate to be reduced to the corresponding alcohols. Nitriles and primary amides were inert to this hydride system, whereas tertiary amide underwent slow reduction. Nitroethane and nitrobenzene were reduced slowly, however azobenzene and azoxybenzene were quite inert. Cyclohexanone oxime evolved 1 equiv. of hydrogen rapidly, but no further reduction was observed. Phenyl isocyanate and pyridine N-oxide were proceeded slowly, showing 1.74 and 1.53 hydride uptake, respectively in 24 hours. Diphenyl disulfide was reduced rapidly, whereas di-n-butyl disulfide, sulfone and sulfonic acids were inert or sluggish. n-Hexyl iodide and benzyl bromide reacted rapidly, but n-octyl bromide, n-octyl chloride, and benzyl chloride reacted very slowly.

Reaction of Bis(diethylamino)aluminum Hydride in Tetrahydrofuran with Selected Organic Compounds Containing Representative Functional Groups

  • Jin Soon Cha;Oh Oun Kwon;Jong Mi Kim
    • Bulletin of the Korean Chemical Society
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    • v.15 no.2
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    • pp.132-138
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    • 1994
  • Bis(diethylamino)aluminum hydride was utilized in a systematic study of the approximate rates and stoichiometry of the reaction of excess reagent with 55 selected organic compounds containing representative functional groups under standardized conditions (THF, $0^{\circ}C$, reagent to compound=4 : 1) in order to define the characteristics of the reagent for selective reductions. The reducing action of BEAH was also compared with that of the parent aluminum hydride. The reducing action of the reagent is quite similar to that of aluminum hydride, but the reducing power is much weaker. Aldehydes and ketones were readily reduced in 1-3 h to the corresponding alcohols. However, unexpectedly, a ready involvement of the double bond in cinnamaldehyde was realized to afford hydrocinnamyl alcohol. The introduction of diethylamino group to the parent aluminum hydride appears not to be appreciably influential in stereoselectivity on the reduction of cyclic ketones. Both p-benzoquinone and anthraquinone utilized 2 equiv of hydride readily without evolution of hydrogen, proceeded cleanly to the 1,4-reduction products. Carboxylic acids and acid chlorides underwent reduction to alcohols slowly, whereas cyclic anhydrides utilized only 2 equiv of hydride slowly to the corresponding hydroxylacids. Especially, benzoic acid with a limiting amount of hydride was reduced to benzaldehyde in a yield of 80%. Esters and lactones were also readily reduced to alcohols. Epoxides examined all reacted slowly to give the ring-opened products. Primary and tertiary amides utilized 1 equiv of hydride fast and further hydride utilization was quite slow. The examination for possibility of achieving a partial reduction to aldehydes was also performed. Among them, benzamide and N,N-dimethylbenzamide gave ca, 90% yields of benzaldehyde. Both the nitriles examined were also slowly reduced to the amines. Unexpectedly, both aliphatic and aromatic nitro compounds proved to be relatively reactive to the reagent. On the other hand, azo- and azoxybenzenes were quite inert to BEAH. Cyclohexanone oxime liberated 1 equiv of hydrogen and utilized 1 equiv of hydride for reduction, corresponding to N-hydroxycyclohexylamine. Pyridine ring compounds were also slowly attacked. Disulfides were readily reduced with hydrogen evolution to the thiols, and dimethyl sulfoxide and diphenyl sulfone were also rapidly reduced to the sulfides.