• Journal of the Korean Applied Science and Technology
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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.

• Bulletin of the Korean Chemical Society
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• 제23권7호
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• pp.1003-1010
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• 2002

Caspase 3, a member of cysteine protease family, is well known as a major apoptosis effector and is involved in cell death as a result of ischemic diseases such as stroke and myocardial infarction, therefore the inhibition of caspase 3 may protect those apoptotic cell damages. During the high-throughput screening of the compounds from the Korea Chemical Bank, berberine derivatives (A and B), an isoquinoline alkaloid, have been identified as potential inhibitors for caspase 3. Based on this finding we carried out molecular modeling study to identify the pharmacophoric elements of berberine structure which interact with a substrate-recognition binding site of caspase 3 and came up with several novel scaffolds. In this report, we will discuss the molecular modeling, syntheses and the enzyme inhibitory activities of these novel compounds.

• Journal of the Korea Academia-Industrial cooperation Society
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• 제14권11호
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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.

• Archives of Pharmacal Research
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• 제20권2호
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• pp.138-143
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• 1997

5-Aryl-2,3-dihydroimidazo[2,1-a]isoquinolines were reported to have strong antitumor activity and one of the derivatives such as $5-[4^{l}$ -(piperidinomethyl)phenyl]-2,3-dihydroimidazo[2,1-a] isoquinoline (1, SDZ 62-434) was found to be more effective than the clinical cytostatic agent edelfosine (2) in in vitro and in vivo assays. Currently SDZ 62-434 is in clinical trials in Europe. The structure-activity relationship studies of SDZ 62-434 showed that compounds with substitution on ring A were less active than the lead compound. Ring B in SDZ 62-434 was essential for the activity because compounds without B ring had no antitumor activity. Among the 3-arylisoquinolin-1-one derivatives, $3-[4^{I}$-(piperidinomethyl)phenyl] substituted analog had no antitumor activity but simple phenyl substituted compound, such as 4, showed the most potent antitumor activity in various human tumor cell lines.

• Archives of Pharmacal Research
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• 제20권3호
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• pp.264-268
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• 1997

In order to study the structure-activity relationship of 7, 8-dimethoxy-2-methyl-3-(4, 5-methylenedioxy-2-vinylphenyl)isoquinoline-1(2H) -one (2), which has exhibited significant antitumor activity, chemical modifications of 2 were performed to yield the corresponding products (3-7). Further systematic uses of an efficient procedure for the synthesis of 3-arylisoquinoline derivatives produced the substituted compounds (9a-9g), which were tested for in vitro antitumor activity against five different human cancer cell lines.

• Proceedings of the Korea Society of Environmental Toocicology Conference
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• 한국환경독성학회 2003년도 춘계학술대회
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• pp.188-188
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• 2003

Examination was made of the urinary metabolite(s) of CKD-712, which is a chiral compound, named S-YS49 derived from higenamine (one component of Aconite spp.) derivatives. First of all, to analyze the metabolite(s) of CKD-712, a simple and sensitive detection method for CKD-712 was developed by using gas chromatography-mass spectrometry GC/MS). Urine was collected from adult male Sprague-Dawley rats 250${\pm}$10g) in metabolic cage for 24hr after oral administration of 100 mg/kg of CKD-712. The recovery of CKD-712 after extraction and concentration with AD-2 resin column was above 90 % from rat urine. The detection limits of CKD-712 in urine was approximately 0.1 ng/mL. It has well been suggested that isoquinoline possessing catechol moiety such as CKD-712 should be subjected to the catechol-O-methyl kransferase activity in vivo. We detected three major peaks of presumed CKD-712 metabolites in the total ion chromatogram obtained from the rat urine sample after oral administration of CKD-712. From these results, it is assumed that the urinary metabolites are mono-methylation in the naphthyl moiety (metabolite I ), methylation at the C-6 or 7 hydroxy group in the isoquinoline moiety and hydroxylation at in the naphthyl moiety (metaboliteII), and methylation at the C-6 or 7 hydroxy group in the isoquinoline moiety (metaboliteIII).

• YAKHAK HOEJI
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• 제40권2호
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• pp.131-134
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• 1996

3,4-Dimethoxyphenethyl amine(1) and 3,4-dimethoxybenzaldehyde were converted to compounds(4) through sucessive condensation and reduction reaction. Compound(4) was treated with methylthioacetyl chloride to give compound(5) then m-chloroperbenzoic acid(m-CPBA) treatment of compound(5) produced S-oxide(6). To obtain isoquinoline derivative(7),(8), compound(6) were treated with p-TsOH. Xylopinine(9) and it's derivatives(10) were produced by Bischler-Napieralski reaction.

• 한국정보디스플레이학회:학술대회논문집
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• 한국정보디스플레이학회 2002년도 International Meeting on Information Display
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• pp.479-482
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• 2002

Benzylideneacetophenones are known as chalcones[1]. The chalcone has been known to be a photo-isomerizable and photo-dimerizable chromophore. The chalcone derivatives were prepared by base-catalyzed condensation of aldehydes and acetophenones, which were substituted with various alkyl chains. The synthesized chalcone was introduced into the t-BOC protected diamine through William synthesis reaction. Photocrosslinkable polyimide was prepared via one-step imidization reaction of DOCDA (5-(2,5-dioxotetrahydro furyl}-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride) and the chalcone introduced diamine using isoquinoline (5 wt%) in m-cresol. The polyimide solutions were spin-coated onto the quartz, silicone wafer and glass substrates and the obtained thin films were irradiated obliquely with linearly polarized UV light.

• The Korean Journal of Physiology and Pharmacology
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• 제9권5호
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• pp.283-289
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• 2005

Endothelium, particularly pulmonary endothelium, is predisposed to injury by reactive oxygen species (ROS) and their derivatives. Heme oxygenase (HO) has been demonstrated to provide cytoprotective effects in models of oxidant-induced cellular and tissue injuries. In the present study, we investigated the effects of YS 49 against oxidant [tert-butylhydroperoxide (TBH)]-induced injury using cultured sheep pulmonary artery endothelial cells (SPAECs). The viability of SPAECs was determined by quantifying reduction of a fluorogenic indicator Alamar blue. We found that TBH decreased cell viability in a timeand concentration-dependent manner. YS 49 concentration- and time-dependently increased HO-1 induction on SPAECs. As expected, YS 49 significantly decreased the TBH-induced cellular injury. In the presence of zinc protophorphyrin, HO-1 inhibitor, effect of YS 49 was significantly inhibited, indicating that HO-1 plays a protective role for YS 49. Furthermore, YS 49 showed free radical scavenging activity as evidenced by 1,1-diphenyl-2-picrylhydrazyl (DPPH) and inhibition of lipid peroxidation. However, YS 49 did not inhibit apoptosis induced by lipopolysaccharide (LPS) in SPAECs. Taken together, HO-1 induction along with strong antioxidant action of YS 49 may be responsible for inhibition of TBH-induced injury in SPAECs.