• 한국산학기술학회논문지
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• 제14권11호
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• pp.6000-6007
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• 2013

유기합성 과정에서 응용범위가 넓고 안정한 알코올류의 산화제에 대해 많은 연구가 진행 되고 있으며, 그중에서도 Cr(VI)-계열의 시약들이 산화제로 널리 이용되어 왔다. 그러므로 유기 용매에 잘 용해되고, 일차 알코올을 알데히드까지만 산화시키는 산화제의 합성과 그에 따르는 메카니즘 규명이 필요하게 되었다. Cr(VI)-헤테로고리 착물인 Cr(VI)-isoquinoline를 합성하여, 적외선 분광광도법(IR), 유도결합 플라즈마(ICP) 등으로 구조를 확인하였다. 또한 여러가지 용매 하에서 Cr(VI)-isoquinoline를 이용하여 벤질 알코올의 산화반응을 측정한 결과 유전상수(${\varepsilon}$) 값이 큰 용매 순서인 시클로헥센<클로로포름<아세톤$CH_3$, m-Br, m-$NO_2$)을 효과적으로 산화시켰다. 여기서 전자받개 그룹들은 반응 속도가 감소한 반면에 전자주개 치환체들은 반응속도를 증가시켰고, Hammett 반응상수(${\rho}$) 값은 -0.69(308K) 이였다. 그러므로 본 실험에서 알코올의 산화반응 과정은 먼저 크로메이트 에스테르 형성과정을 거친 후, 속도결정단계에서 수소화 전이가 일어나는 메카니즘임을 알 수 있었다.

• 방사선산업학회지
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• 제4권1호
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• pp.1-6
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• 2010

The purpose of this study is to synthesize the radio fluorine labelled isoquinoline salt derivative as new radiopharmaceutical for imaging tumors using positron emission tomography (PET). The planarity of isoquinoline allows to inhibit topoisomerase or intercalate between adjacent DNA base pairs, which result in producing double strand breaks in the DNA and a cell death. Therefore, the isoquinoline has seemed to have a potential anticancer activity. In order to obtain 2-(5-[$^{18}F$]fluoropentylisoquinolinium salt with good radiochemical yield, tosylated precursors have been synthesized. The labelling reaction was carried out for 30 minute in HMPA at $120^{\circ}C$. The radiochemical yield was about 50~60%.

• 약학회지
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• 제45권5호
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• pp.442-447
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• 2001

Aerial parts of Corydalis ochotensis Turcz. (Papaveraceae) has been used as a folk medicine in China for its antipyretic, analgesic and diuretic properties, which is widely distributed in Korea. Phytochemical study of the aerial parts of C. ochotensis led to the isolation of three isoquinoline alkaloids, (+)adlumidine, govadine and (-)severtzine, together with quercetin, rutin and tridecanoic acid. These compounds were established by conventional methods of analysis and identified by $^{1}$H,$^{13}$ C-NMR, and MS data.

• 한국응용과학기술학회지
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• 제15권2호
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• pp.49-57
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• 1998

This study is to develop a new synthetic method for the nitroarenes via non-electrophilic substitution. Direct nitration at the C-1 position of isoquinoline has never been reported and substitution in isoquinoline under the normal nitration condition occurs at C-5 and C-8. We have demonstrated a facile one-step sythetic method for the nitration of isoquinolines at the C-1 position, which involves the electrophilic attack of a $DMSO-Ac_2O$ complex, followed by nucleophilic addition of nitrate ion to this intermediate. Since the reaction is simple and mild, this method has preparative merit since 1-nitroisoquinolines are not readily accessible by other methods. Application to the synthesis of poly nitroarenes from the corresponding anilines was also described.

• Journal of Microbiology and Biotechnology
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• 제28권2호
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• pp.262-266
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• 2018

Phytochemicals have been considered as alternatives for synthetic fungicides because of their biodegradability and low toxicity. In this study, we found that the methanolic extract of Corydalis ternata suppressed the development of plant diseases caused by Puccinia triticina and Colletotrichum coccodes. As the antifungal substance, three isoquinoline alkaloids (dehydrocorydaline, stylopine, and corydaline) were isolated from C. ternata. These active compounds also exhibited in vivo antifungal activity against P. triticina and C. coccodes. Taken together, our results suggest that C. ternata and its active compounds can be used to control plant diseases.

• 생약학회지
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• 제9권2호
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• pp.57-72
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• 1978

The constituents of Ranunculaceae plants are summerized from more than one hundred of papers. Fifteen steroidal alkaloids, thirty two of terpenoids (diterpenes and triterpenes), fifty four isoquinoline alkaloids are recorded. Thirty three papaverines, eighteen berberines, and three hydrastines belong to isoquinoline group. Besides, of alkaloids a number of glycosides are also found. Adonis glycoside, famous cardiotonics, from Adonis and cyanogenin glycoside and calthoside D were identified from the leaves of Thalictrum aquilegifolium and Caltha silvestris. Anemonin, the irritating substance, found in Pulsatilla grandiz $W_{ENDER}$. Kaempf-erol and dihydrokaempferol were isolated and identified from the leaves of Clematis brachyura ^M_{AXIMOWICZ}$ by author in 1968.

• 분석과학
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• 제30권6호
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• pp.379-389
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• 2017

In this study, we set up an analytical method that can be used for rapid and accurate determination of representative isoquinoline alkaloids in medicinal plants using UPLC-ESI-Q-TOF MS (ultra pressure liquid chromatography-electrospray ionization-quadrupole-time-of-flight mass spectrometry). The compounds were eluted on a C18 column with 0.1 % formic acid and acetonitrile, and separated with good resolution within 13 min. Each of the separated components was characterized by precursor ions (generated by ESI-Q-TOF) and fragment ions (produced by collision-induced dissociation, CID), which were used as a reliable database. We also performed method validation: analytes showed excellent linearity ($R^2$, 0.9971-0.9996), LOD (5-25 ng/mL), LOQ (17-82 ng/mL), accuracy (91.6-97.4 %) as well as intra- and inter-day precisions (RSD, 1.8-3.2 %). In the analysis of Chelidonium majus L., magnoflorine, coptisine, sanguinarine, berberine and palmatine were detected by matching retention times and characteristic fragment ion patterns of reference standards. We also confirmed that, among the quantified components, coptisine was present in the highest quantity. Furthermore, alkaloid profiling was carried out by analyzing the fragment ion patterns corresponding to peaks of unknown components. In this manner, protopine, chelidonine, stylopine, dihydroberberine, canadine, and nitidine were tentatively identified. We also proposed the molecular structure of the fragment ions that appear in the mass spectrum. Therefore, we concluded that our suggested method for the determination of major isoquinoline alkaloids by UPLC-Q-TOF can be useful not only for quality control, but also for rapid and accurate investigation of phytochemical constituents of medicinal plants.

• 대한화학회지
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• 제42권2호
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• pp.150-155
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• 1998

Acetonitrile 용매내에서 isoquinoline과 치한된 benzylbromide의 반응을 압력변화(1~1000bar)에 따라 반응속도론적으로 연구하였다. 속도상수로부터 활성화파라미터들을 TEX>$\(DeltaV^{\neq}, \Delta\beta^{\neq}, \DeltaH^{\neq}, \DeltaS^{\neq}, \DeltaG^{\neq},Ea)$구하였다. 온도가 증가함에 따라 속도상수는 증가 하고, TEX>$\DeltaV^{\neq}, \Delta\beta^{\neq},및 \DeltaS^{\neq}$는 모두 음의 값으로 나타내었다. 치환기효과와 실험 결과로 부터 반응메카니즘을 고찰한 결과 전체적인 반응은 $S_{N}2$반응 메카니즘으로 진행되나, 치환체와 압력변화에 따라 전이상태 구조에 약간의 변화가 있었다.

• Natural Product Sciences
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• 제17권2호
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• pp.108-112
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• 2011

Several isoquinoline alkaloids (1 - 18), which have basic chemical structures as protoberberine and aporphine skeletones, were evaluated for their inhibitory activities on AChE and BuChE. Among them, compounds 3, 4, 6, 8 and 12 showed the potent AchE activity with the $IC_{50}$ values ranging from $10.2{\pm}0.5\;{\mu}M$ to $24.5{\pm}1.6\;{\mu}M$, meanwhile, compound 14 - 17 exhibited strong inhibitory activity with $IC_{50}$ values from $2.1{\pm}0.2$ to $5.5{\pm}0.3\;{\mu}M$. Compounds 14 - 17 exhibited selective inhibition for AChE compared with BuChE. The isoquinoline alkaloid possesses aromatic methylenedioxy groups and quaternary nitrogen atoms are crucial for the anti-cholinesterase inhibitory activity.

• 대한화학회지
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• 제34권6호
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• pp.534-538
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• 1990

H$_2$O을 용매로 하여 헤테로고리 염기인 이소퀴놀린과 CrO$_3$를 반응시켜 Cr(Ⅵ)화합물인 [$C_9H_7$NH]$_2Cr_2O_7$을 얻었다. 이 화합물은 비흡수성이면서 물에 잘 녹았다. 그리고 원소분석, 적외선 분광법으로 이 화합물의 구조가 [$C_9H_7$NH]$_2Cr_2O_7$임을 확인하였다. 또한, 이 화합물이 여러 가지 알코올을 알데히드나 케톤으로 전환시킬 수 있는 산화제로 작용하는가를 알아보기 위하여 알릴, 일차, 이차 알코올을 각각 산화반응에 이용한 결과 알코올들에 대해 효율적인 산화제로 작용하였다.