• Title/Summary/Keyword: Isoquinoline

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A Study for Kinetics and Oxidation Reaction of Substituted Benzyl Alcohols using Cr(VI)-Heterocyclic Complex(Cr(VI)-Isoquinoline) (Cr(VI)-헤테로고리 착물(Cr(VI)-Isoquinoline)를 이용한 치환 벤질 알코올류의 산화반응과 속도론에 관한 연구)

  • Park, Young-Cho;Kim, Young-Sik
    • Journal of the Korea Academia-Industrial cooperation Society
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    • v.14 no.11
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    • pp.6000-6007
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    • 2013
  • Cr(VI)-heterocyclic complex[Cr(VI)-isoquinoline] was synthesized by the reaction between of heterocyclic compound(isoquinoline) and chromium trioxide, and characterized by IR and ICP analysis. The oxidation of benzyl alcohol using Cr(VI)-isoquinoline in various solvents showed that the reactivity increased with the increase of the dielectric constant(${\varepsilon}$), in the order : cyclohexene$CH_3$, m-Br, m-$NO_2$). Electron- donating substituents accelerated the reaction, whereas electron acceptor groups retarded the reaction. The Hammett reaction constant(${\rho}$) was -0.69(308K). The observed experimental data have been ratiolized. The hydride ion transfer causes the prior formation of a chromate ester in the rate-determining step.

Synthesis of 18F Labelled Isoquinoline Salt for PET Imaging (PET 영상용 18F 표지 Isoquinolinium Salt의 합성)

  • Kim, Hee Jung;Kim, Dong Yeon;Kim, In Jong;Park, Jeong Hoon;Lee, Heung Nae;Kim, Sang Wook;Hur, Min Goo;Choi, Sang Moo;Yang, Seung Dae;Yu, Kook Hyun
    • Journal of Radiation Industry
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    • v.4 no.1
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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%.

Isoquinoline Alkaloids from the Aerial Parts of Corydalis ochotensis (눈괴불주머니 지상부의 Isoquinoline alkaloid성분)

  • 이기택;엄상섭;은재순;신태용;임종필
    • YAKHAK HOEJI
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    • v.45 no.5
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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.

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Synthesis of Aniline and Isoquinoline derivatives using Deamination and Nitration (Deamination과 Nitration반응을 이용한 아닐린과 Isoquinoline 유도체의 합성)

  • Yoon, Cheol-Hun;Lee, Ki-Chang
    • Journal of the Korean Applied Science and Technology
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    • v.15 no.2
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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.

In Vivo Disease Control Efficacy of Isoquinoline Alkaloids Isolated from Corydalis ternata against Wheat Leaf Rust and Pepper Anthracnose

  • Han, Jae Woo;Shim, Sang Hee;Jang, Kyoung Soo;Choi, Yong Ho;Kim, Hun;Choi, Gyung Ja
    • Journal of Microbiology and Biotechnology
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    • v.28 no.2
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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.

Chemical Constituents of Ranunculaceous Plants (모낭과식물의 성분(成分))

  • Chung, Dong-Kyu
    • Korean Journal of Pharmacognosy
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    • v.9 no.2
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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.

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Determination of isoquinoline alkaloids by UPLC-ESI-Q-TOF MS: Application to Chelidonium majus L.

  • Jeong, Won Tae;Lim, Heung Bin
    • Analytical Science and Technology
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    • v.30 no.6
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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.

Kinetic Study on the Reaction of para-substitued Benzylbromide with Isoquinoline under High Pressure (고압하에서의 이소퀴놀린과 브롬화 벤질류의 반응에 관한 속도론적인 연구)

  • Kim, Young Cheul;Lim, Jong Wan;Choi, Sung Yong
    • Journal of the Korean Chemical Society
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    • v.42 no.2
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    • pp.150-155
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    • 1998
  • Kinetic studies on the reaction of isoquinoline with para-substituted benzylbromides were conducted under various pressures (1 ~1000 bar) in acetonitrile. From the rate constants obtained, the activation parameters such as$\DeltaV^{\neq}, \Delta\beta^{\neq}, \DeltaH^{\neq}, \DeltaS^{\neq}, \DeltaG^{\neq}$ and Ea were evaluated. Reaction rate increasing the pressure and temperature. The activation compressibility coefficient and the activation entropy showed negative values. From the substituent effect and the results, it was found that the reaction proceeds through $S_N2$ mechanism, but the structure of transition state was slightly changed with substituents and pressure.

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Cholinesterase Inhibitory Activities of Alkaloids from Corydalis Tuber

  • Hung, Tran Manh;Thuong, Phuong Thien;Nhan, Nguyen Trung;Mai, Nguyen Thi Thanh;Quan, Tran Le;Choi, Jae-Sue;Woo, Mi-Hee;Min, Byung-Sun;Bae, Ki-Hwan
    • Natural Product Sciences
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    • v.17 no.2
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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.

A Study for Oxidation Reaction of Alcohols with Cr (Ⅵ)-Isoquinoline Compound (Ⅰ) (Cr (Ⅵ)-Isoquinoline 화합물에 의한 알코올들의 산화반응에 관한 연구 (Ⅰ))

  • Yang, Jeong Seong;Park, Yeong Jo;Baek, Hyeong Cheol
    • Journal of the Korean Chemical Society
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    • v.34 no.6
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    • pp.534-538
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    • 1990
  • Chromium(Ⅵ) compound, [$C_9H_7$NH]$_2Cr_2O_7$ has been prepared by the reaction of isoquinoline with chromium trioxide under the presence of water. [$C_9H_7$NH]$_2Cr_2O_7$ is nonhydroscopic and dissolved in water very well. Structure of [$C_9H_7$NH]$_2Cr_2O_7$ is identified by FTIR spectra and elemental analysis data. The ability of [$C_9H_7$NH]$_2Cr_2O_7$ for the oxidation of alcohols were examined in methylene chloride. [$C_9H_7$NH]$_2Cr_2O_7$ was found as efficient oxidizing agent for the conversion of allyl, primary and secondary alcohols to the corresponding aldehydes or ketones.

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