• 대한화학회지
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• 제39권6호
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• pp.434-439
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• 1995

산소, 질소, 그리고 황 주개 원자의 이염기성 세자리 리간드로서 S-methyl-3(-2-hydroxy-x-phenyl)methylenedithiocarbazate($L^1:x=5-H$)와 그 유도체($L^2:x=5-CH_3,\;L^3:x=3CH_3O,\;L_4:x=5,6-C_4H_4\; 그리고\;x^5:ㅌ=5-NO_2$)의 6-배위 몰리브덴(V)-산소 착물, ($R_4N$)[MoO(NCS)_2L](R=CH_3,\;C_3H_5,\;n-C_4H_9)$들을 합성하고 원소분석, 몰 전도도, UV-Vis, IR, $1^H$ NMR 그리고 CV 등을 이용하여 착물의 구조와 분광학적 및 전기화학적 성질 등을 조사하였다.

• 한국식품과학회지
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• 제20권2호
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• pp.157-163
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• 1988

Propylene glycol 용매계에서 0.5M DL-alanine(${\alpha}-amino-propionic acid$) 와 0.5M D-glucose 를 $100^{\circ}C,\;120^{\circ}C$ 및 $140^{\circ}C$에서 각각 20분, 2시간 반응시켜 생성되는 휘발성 화합물을 분석하고 반응온도와 시간이 갈색화반응 및 휘발성 화합물생성에 미치는 영향을 조사하였다. 갈색화반응 및 휘발성 화합물생성에 미치는 영향을 조사하였다. 갈색화반응은 반응온도와 시간이 증가함에 따라 급격히 증가 하였다. 휘발성 화합물은 7종의 alkylpyrazine, 4종의 pyrrole, 3종의 furan, 1종의 furanone 그리고 기타성분으로 2-hydroxy-3-methyl-2-cyclopenten-1-one을 포함하여 11종이 확인되었으며 pyrazine, pyrrole 및 furan화합물의 생성량은 반응온도가 높아지고 반응시간이 길어짐에 따라 급격히 증가하였다. 또한 alanine과 glucose의 마이야르 반응에 의해 생성되는 구수한 카라멜냄새 및 설탕 탄냄새(burnt sugar-like)는 주로 2-hydroxy-3-methyl-2-cyclopenten-1-one, 2, 5-dimethyl-4-hydroxy-3(2H)-furanone과 같은 함 산소화합물과 pyrazine, pyrrole과 같은 함 질소화합물에 의해 생성되는 것으로 추정되었다.

• Bulletin of the Korean Chemical Society
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• 제28권12호
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• pp.2324-2328
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• 2007

Organic fluorine chemistry produces many useful products. This paper elucidates the reaction of ethyl-4,4- difluoro-2-iodo-5-oxo-5-phenylpentanoate (2) with primary amines in a one-pot scheme. The reaction produced a series of β-fluoropyrrole derivatives at ambient temperatures. In this reaction, the less bulky the primary amine the higher was the resultant yield. When (2) and aqueous methylamine (40%) were allowed to react below 0 oC, 5-(ethoxycarboxyl)-1-methyl-3,3-difluoro-2-hydroxy-2-phenylpyrrolidine, an intermediate molecule for 2-ethyl-4-flouro-1-methyl-5-phenylpyrrole-2-carboxylate (5), was isolated first. Then, (5) reacted with hydroperchloric acid and acetic anhydride to form 5-(ethoxycarboxyl)-1-methyl-3,3-difluoro-2- phenylpyrrolinium perchlorate (6), which was converted to 2-ethyl-4-flouro-1-methyl-5-phenylpyrrole-2- carboxylate gradually in the presence of a base. Our experiments demonstrate that the formation of 2-ethyl-4- flouro-1-methyl-5-phenylpyrrole-2-carboxylate occurs via both one-pot schemes and stepwise pathways, depending on the reaction conditions. The isolation and characterization of the isolated intermediate (6) suggest an anionic pathway for this reaction.

• 한국연초학회지
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• 제21권2호
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• pp.119-127
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• 1999

This study was conducted to evaluate the effect of cigarette papers, flax and wood, on the delivery of mainstream smoke. The main components of cigarette papers were cellulose, hemicellulose, lignin, and pectin. Lignin contents, known as precursor of smoke's phenolic compounds, of the flax and wood cigarette papers were 5.8% and 10.6%, respectively. The pyrolysis products of cigarette papers were similar by the profile of total ion chromatogram. But, the area % of some components, such as 1,3-cyclopentanedione, 3,5- dimethyl cyclopentane-1,2-dione, 2-hydroxy-3-methyl-2-cyclopentenone, dihydro-2(3H)-furanone, 3-methyl-2(5H)-fruanone, and 5-methyl-2-furaldehyde delivered through pyrolysis of the flax cigarette paper were higher than that of wood cigarette paper. Otherwise, the area % of some components, such as 2-methyl-cyclopentene-l-one), 2,3-butanedione, 2-cyclopentene-l-one, and 5-hydroxy-2-methyl-furaldehyde, 2-furaldehyde delivered through pyrolvsis of the wood cigarette paper were higher than that of flax cigarette paper. To identify the difference between two cigarette papers, we used the cigarette column filled with the cut cigarette paper instead of the cut tobacco leaf. The amounts of semi-volatile fraction delivered from flax cigarette paper was more than that of wood cigarette paper. But, by using the cut tobacco, there was no big difference of delivery amount between flax and wood cigarette papers. Also, aroma of TPM by collecting from brening cut tobacco wrapped in flax and wood papers showed a different pattern by the electonic nose system. Although the difference between two cigarette papers by using the cut tobacco was smaller than that of cut cigarette paper, this result indicated that the fax and wood had the different effects on the delivery of smoke components as shown in the sensory test results.

• Bulletin of the Korean Chemical Society
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• 제32권6호
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• pp.1931-1935
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• 2011

The synthesis of carbocyclic analogues of normal nucleosides has grown exclusively since they have shown potential antiviral and antitumor activities. Radiolabeled cis-1-[4-(hydroxy-methyl)-cyclopent-2-enyl]-5-$[^{124}I]$-iodocytosine (carbocyclic d4IC) and cis-1-[4-(hydroxy-methyl)-cyclopent-2-enyl]-5-(2-$[^{124}I]$iodovinyl)cytosine(carbocyclic d4IVC) were synthesized. The synthetic route employed Pd(0)-catalyzed coupling reaction together with organotin and exchange reaction for radioiodination as key reactions. Carbocyclic $[^{124}I]$d4IC gave more than 75% radiochemical yield with greater than 95% radiochemical purity. Carbocyclic $[^{124}I]$d4IVC gave more than 80% radiochemical yield with greater than 95% radiochemical purity.

• 생약학회지
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• 제17권1호
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• pp.67-72
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• 1986

A stereospecific synthesis of 3-methyl-5-(1-hydroxy-4-oxo-2,6,6-trimethyl-2-cyclohexen-1-yl)-cis, trans-2,4-pentadienoic acid (abscisic acid) from ${\alpha}-ionone$ has been investigated. Ethyl 5-(2,6,6-trimetyl-2-cyclohexen-1-yl)-trans-4-penten-2-ynoate $({\alpha},{\beta}-acetylenic\;ester)$, which was synthesized from alpha-ionone in two steps, was stereospecifically converted in good yield into ethyl 3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-cis, trans-2, 4-pentadienoate $({\alpha}-ionylideneacetate)$ by the conjugate addition of lithium dimethylcuprate at $-78^{\circ}C$. Basic hydrolysis of the ethyl ${\alpha}-ionylideneacetate$ gave an abscisic acid precursor, 3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-cis, trans-2,4-pentadienoic acid, which can be oxidized to yield abscisic acid.

• 현장농수산연구지
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• 제22권1호
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• pp.65-77
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• 2020

시중에서 많이 판매되는 국화차의 대명사인 감국(Dendranthema indicum (L.) DesMoul.)을 산업화하기 위해, 2018년 가을에 자생지에서 감국(Dendranthema indicum (L.) DesMoul.) 종자를 채취하여 냉장 보관 후 종자를 발아시켰다. 어린 묘종은 2, 3, 4월에 노지에 시기별, 간격별에 따른 꽃의 수확량과 잎, 줄기의 성장에 미치는 영향을 살펴보기 위한 실험을 하였다. 감국(Dendranthema indicum (L.) DesMoul.) 꽃을 채취한 후 잎, 줄기를 채취하여 성분을 분석한 결과는 아래와 같다. 1. 국화 묘종을 정식시기별로 심었을 때 꽃은 4월에 정식한 처리구에서 17.1개로 가장 많았다. 꽃의 지름은 2.9cm, 꽃수는 16개, 생체중은 6.5~6.6g, 건체중은 1.1~1.2g이었다. 잎은 3, 4월에 심은 처리구에서 46~47개, 엽장은 5.2~5.3cm, 옆폭은 3.5~3.6cm이었다. 2. 국화 묘종을 정식거리별로 심었을 때 꽃수는 20×20cm 간격으로 심었을 때 16.2개로 가장 작았고, 30~50cm 간격에서는 16.8~17.1개 이었다. 꽃 지름은 2.7~2.8cm, 꽃잎수는 8개, 꽃잎 길이는 0.8cm, 꽃 한 개의 생체중은 6.5~6.6g이었다. 잎수는 30×30cm, 40×40cm에서 47개로 가장 많았고, 엽장은 50×50cm처리구에서는 가장 긴 6.2cm로 나타났지만 그 외 처리구에서는 5.2cm이었다. 3. 국화 잎+줄기의 추출수율은 7.93%였고, 추출 용매색은 50, 60%는 연녹색, 70, 80, 90, 100%는 녹색으로 나타났다. 감국 꽃은 추출수율이 7.58%, 추출 용매색은 50, 60, 70%에서는 연노란색, 80, 90%에서는 노란색, 100%에서는 진노란색이었다. 4. 국화 꽃에 함유된 성분은 gallic acid, 4-hydroxy benzoic acid, methyl gallate, 4-hydroxy-3-methoxy benzoic, caffeic acid, salicylic acid, p-coumaric acid, sinapic acid, naringin, 4-melthoxyben, flavone 등 11가지 성분을 확인하였다. 함량은 29.200~36.900ppm이었다. 5. 국화 잎+줄기에 함유된 성분은 salicylic acid가 6,129.526ppm으로 나타났고, 다음으로 4-methoxyben 1,966.714ppm이었다. 함유량이 10ppm 이하로 나타난 것은 methyl gallate 8.197ppm, 4-hydroxy-3-methoxy benzoic 6.994ppm, caffeic acid 5.566 ppm, flavone 4.522ppm, p-coumaric acid 3.787 ppm, gallic acid 1.893ppm이었다.

• Natural Product Sciences
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• 제28권1호
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• pp.1-5
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• 2022

Two 2H-1-benzopyran derivatives, methyl 8-hydroxy-2,2-dimethyl-2H-1-benzopyran-5-carboxylate (1) and methyl 8-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carboxylate (2), including a new compound (1) were isolated from the twigs of Chaenomeles sinensis. Their chemical structures were characterized based on analysis of NMR data including ¹H and ¹³C, COSY, HSQC, and HMBC and HRMS data. The isolated compounds (1 and 2) were assessed for their anti-neuroinflammatory activity by measuring inhibition levels of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells and for their neurotrophic activity by the secretion of nerve growth factor (NGF) in C6 cells. Compounds 1 and 2 exhibited powerful anti-neuroinflammatory effects with IC₅₀ values of 17.14 and 19.30 μM, respectively, without cell toxicity, and also showed moderate effects on the stimulation of NGF secretion levels with 113.15 ± 3.54 and 130.20 ± 8.03%, respectively. The biosynthetic pathway of 1 and 2 was proposed that they would be derived from a protocatechuic acid and an isoprenyl unit.

• 약학회지
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• 제52권6호
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• pp.514-519
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• 2008

We developed a convenient synthetic route to 3-alkylated 2-phenyl-4-quinolone derivatives (4a-h and 5a-c), which were expected to retain antitumor activity. A series of 2,3-dihydro-2-hydroxy-2-phenyl-4-quinolones (3a-h) was synthesized through dehydration, dealcoholation and hydration using acid-catalyzed one-pot reaction from anilines and ethyl benzoylacetates. 3-Methyl (or 3,3-dimethyl)-2-phenyl-4-quinolone derivatives 4 and 5 were synthesized from 3a-h through the methylation using methyl iodide. Formation of quinolone nucleus was undertaken with p-toluenesulfonic acid (p-TSA) at $90{\sim}110^{\circ}C$ in toluene for 3${\sim}$7.5 hr over the Dean-Stark apparatus. The key intermediates in these preparations are ${\beta}$-ketoesters 2a-h, which can be readily obtained from the corresponding anilines 1a-e by reaction with ethyl bezoylacetates.

• Applied Biological Chemistry
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• 제7권
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• pp.105-117
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• 1966

acaricide로 알려진 phthalimidomethyl O,O-dimethyl phosphorodithioat (Imidan)을 수도(水稻)에 살포(撒布)했을 때 Imidan과 그 대사물질(代謝物質)이 식물(植物)의 생육(生育)에 미치는 영향(影響)을 연구(硏究)하기 위하여 본(本) 실험(實驗)을 하였으며 이의 결과(結果)를 요약(要約)해 보면 다음과 같다. (1) Imian의 대사물질(代謝物質)로 예상(豫想)되는 다음의 8가지 화합물(化合物)을 합성(合成) 또는 정제(精製)하여 공시약제(供試藥劑)로 사용(使用)하였다. (a) N-Hydroxy methyl phthalimide (b) Phalimide (c) Phthalamdic acid (d) Phthalic acid (e) Anthranilic acid (f) p-amino benzoic acid (g) p-hydroxu benzoic acid (h) Benzoic acid (2) 상기(上記) 물질중(物質中)에서 (a),(c),(d),(e)와 Imidan의 각(各) 10 ppm과 20 ppm 의 Buffer Solution 을 만들어 밀 종자(種子)를 가지고 coleoptile straight growth test를 해 본 결과(結果) Imidan 은 10 ppm 과 20 ppm에서 모두 control 보다 생장(生長)의 촉진효과(促進?果)를 보였으며 기중(其中) phthalamidic acid 10 ppm 이 가장 좋은 성적(成績)을 보였다. 이것으로 보아 Imidan 자체(自體)는 생장(生長) 억제(抑制)의 효과(?果)를f 보이나 이것이 일단(一但) 생체내(生體內)에서 가수분해(加水分解)를 비롯한 각종(各種) 대사작용(代謝作用)을 받으면 그 대사산물(代謝産物)이 식물생장(植物生長)을 촉진(促進)하는 효과(?果)를 보이는 것 같다. (Table 1, Fig. 1 참조(參照)) (3) xylene을 용매(溶媒)로 하여 Imidan 유제(乳劑)를 만들고 이것을 희석(稀釋)하여 20 ppm, 100 ppm 및 200 ppm 의 각(各) 농도(濃度) 유화액(乳化液)을 조제(調製)한 후 이것을 배지(培地)로 하여 수도종자(水稻種子)를 발아(發芽)시킨 후 12 일(日)에 shoot와 root의 길이를 측정(測定)하였다. 이의 결과(結果)를 보면 root는 Imidan 20 ppm에서, shoot 는 Imidan 100 ppm에서 모두 xylene만의 유제구(乳劑區)인 control 보다 좋은 효과(?果)를 보였으며 여기에서 흥미(興味)있는 것은 용매(溶媒)로 사용(使用)된 xylene은 수도종자(水稻種子) 뿌리의 발육(發育)에 심(甚)한 억제효과(抑制效果)를 보이는 것 같다. (Table 2, Table 5 참조(參照)) (4) 벼를 pot에 심고 2회(回)에 걸쳐 control, Imidan, N-hydroxy methyl phthalimide, anthranilic acid 및 phthalimide의 10, 25, 50, 100 ppm 농도(濃度)의 각(各) 유제(乳劑)를 살포하고 일정기간후(一定期間後) 생육상(生育相)을 조사(調査)하였더니 Imidan 구(區)와 N-hydroxy methyl phthalimide 구(區)가 control 보다 좋은 성적(成績)을 보였다. (5) Imidan 250 ppm 유제(乳劑)를 수도엽면(水稻葉面)에 살포(撒布)하고 3 일(日), 5 일(日), 7 일(日) 및 14일후(日後)에 일정량(一定量)의 엽경(葉莖)을 채취(採取)하여 acetone으로 추출(抽出)k고 acetonitrile을 가지고 prechromatographic piriication 을 거쳐 paper chromatography에 의(依)하여 다음과 같은 대사물질(代謝物質)을 검출(檢出)하였다. Imidan $(Rf:\;0.97{\sim}0.98)$, N-hydroxy methyl phthalimide (Rf: 0.87), phthalimide $(Rf:\;0.86{\sim}0.87)$, phthalamidic acid $(Rf:\;0.13{\sim}0.14)$, phthalic acid $(Rf:\;0.02{\sim}0.03)$, benzoic acid $(Rf:\;0.42{\sim}0.43)$ 및 p-amino benzoic acid 또는 p-hydroxy benzoic acid $(Rf:\;0.08{\sim}0.09)$와 Rf=0.73, 0.59, 0.33, 0.23, 0.07의 미지물질(未知物質)을 검출(檢出)하였다. 또한 3일(日), 5일(日) 등(等) 초기(初期)에서는 미분해(未分解)의 Imidan과 최초(最初)의 가수분해(加水分解) 산물(産物)인 N-hydroxy methyl phthalimide등(等)이 비교적(比較的) 다량(多量)으로 검출(檢出)되었으나 7일(日), 14일(日) 등(等) 후기(後期)에는 생체내(生體內)에서 더 많은 분해(分解)를 받아 상기(上記) 이성분(二成分)은 양(量)이 감소(減少)되고 phthalic acid, phthalamidic acid benzoic acid 및 p-hydroxy benzoic acid 또는 p-amino benzoic acid등(等)의 양(量)이 증가(增加)되는 것을 볼 수있었으며 도체상(稻體上)에 살포(撒布)된 Imidan 은 체내(體內)에 흡수(吸收)되어 14일(日)이 경과(經過)되면 대부분(大部分)이 분해(分解)를 받는 것으로 보여진다. 이상(以上)의 결과(結果)로 보아 Imidan은 자체(自體)로서는 식물생장(植物生長) 촉진작용(促進作用)이 없으나 식물체내(植物體內)에서 여러 가지 대사작용(代謝作用)(enzyme의 작용(作用))을 맡아서 각종(各種) phthaloyl 영향(影響)을 주는 것으로 생각(生覺)된다.