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Novel Syntheses of 5-Aminothieno[2,3-c]pyridazine, Pyrimido[4',5':4,5]thieno[2,3-c]pyridazine, Pyridazino[4',3':4,5]thieno-[3,2-d][1,2,3]triazine and Phthalazine Derivatives

  • El Gaby, Mohamed S.A.;Kamal El Dean, Adel M.;Gaber, Abd El Aal M.;Eyada, Hassan A.;Al Kamali, Ahmed S.N.
    • Bulletin of the Korean Chemical Society
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    • v.24 no.8
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    • pp.1181-1187
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    • 2003
  • Condensation of 4-cyano-5,6-dimethyl-3-pyridazinone 1 with aromatic aldehydes gave the novel styryl derivatives 2a-c. Refluxing of compound 2a with phosphorus oxychloride furnished 3-chloropyridazine derivative 3. Compound 3 was reacted with thiourea and produced pyridazine-3(2H)thione 4. Thieno[2,3-c]- pyridazines 5a-e were achieved by cycloalkylation of compound 4 with halocompounds in methanol under reflux and in the presence of sodium methoxide. Also, refluxing of compound 4 with N-substituted chloroacetamide in the presence of potassium carbonate afforded thienopyridazines 6a-e. Cyclization of compound 6 with some electrophilic reagents as carbon disulfide and triethyl orthoformate furnished the novel pyrimido[4',5':4,5]thieno[2,3-c]pyridazines 12 and 13a-c, respectively. Diazotisation of compound 6 with sodium nitrite in acetic acid produced the pyridazino[4',3':4,5]thieno[3,2-d][1,2,3]triazines 14a-c. Ternary condensation of compound 1, aromatic aldehydes and malononitrile in ethanol containing piperidine under reflux afforded the novel phthalazines 16a-c. Compound 3 was subjected to some nucleophilic substitution reactions with amines and sodium azide and formed the aminopyridazines 17a, b and tetrazolo[1,5-b]-pyridazine 19, respectively. The structures of the synthesized compounds were established by elemental and spectral analyses.

A Novel Chemical Compound for Inhibition of SARS Coronavirus Helicase

  • Lee, Jin-Moo;Cho, Jin-Beom;Ahn, Hee-Chul;Jung, Woong;Jeong, Yong-Joo
    • Journal of Microbiology and Biotechnology
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    • v.27 no.11
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    • pp.2070-2073
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    • 2017
  • We have discovered a novel chemical compound, (E)-3-(furan-2-yl)-N-(4-sulfamoylphenyl) acrylamide, that suppresses the enzymatic activities of SARS coronavirus helicase. To determine the inhibitory effect, ATP hydrolysis and double-stranded DNA unwinding assays were performed in the presence of various concentrations of the compound. Through these assays, we obtained $IC_{50}$ values of $2.09{\pm}0.30{\mu}M$ (ATP hydrolysis) and $13.2{\pm}0.9{\mu}M$ (DNA unwinding), respectively. Moreover, we found that the compound did not have any significant cytotoxicity when $40{\mu}M$ of it was used. Our results showed that the compound might be useful to be developed as an inhibitor against SARS coronavirus.

Endophytic Diaporthe sp. ED2 Produces a Novel Anti-Candidal Ketone Derivative

  • Yenn, Tong Woei;Ring, Leong Chean;Nee, Tan Wen;Khairuddean, Melati;Zakaria, Latiffah;Ibrahim, Darah
    • Journal of Microbiology and Biotechnology
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    • v.27 no.6
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    • pp.1065-1070
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    • 2017
  • This study aimed to examine the anti-candidal efficacy of a novel ketone derivative isolated from Diaporthe sp. ED2, an endophytic fungus residing in medicinal herb Orthosiphon stamieus Benth. The ethyl acetate extract of the fungal culture was separated by open column and reverse phase high-performance liquid chromatography (HPLC). The eluent at retention time 5.64 min in the HPLC system was the only compound that exhibited anti-candidal activity on Kirby-Bauer assay. The structure of the compound was also elucidated by nuclear magnetic resonance and spectroscopy techniques. The purified anti-candidal compound was obtained as a colorless solid and characterized as 3-hydroxy-5-methoxyhex-5-ene-2,4-dione. On broth microdilution assay, the compound also exhibited fungicidal activity on a clinical strain of Candida albicans at a minimal inhibitory concentration of $3.1{\mu}g/ml$. The killing kinetic analysis also revealed that the compound was fungicidal against C. albicans in a concentration- and time-dependent manner. The compound was heat-stable up to $70^{\circ}C$, but its anti-candidal activity was affected at pH 2.

Mechanics model of novel compound metal damper based on Bi-objective shape optimization

  • He, Haoxiang;Ding, Jiawei;Huang, Lei
    • Earthquakes and Structures
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    • v.23 no.4
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    • pp.363-371
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    • 2022
  • Traditional metal dampers have disadvantages such as a higher yield point and inadequate adjustability. The experimental results show that the low yield point steel has superior energy dissipation hysteretic capacity and can be applied to seismic structures. To overcome these deficiencies, a novel compound metal damper comprising both low yield point steel plates and common steel plates is presented. The optimization objectives, including "maximum rigidity" and "full stress state", are proposed to obtain the optimal edge shape of a compound metal damper. The numerical results show that the optimized composite metal damper has the advantages such as full hysteresis curve, uniform stress distribution, more sufficient energy consumption, and it can adjust the yield strength of the damper according to the engineering requirements. In view of the mechanical characteristics of the compound metal damper, the equivalent model of eccentric cross bracing is established, and the approximate analytical solution of the yield strength and the yield displacement is proposed. A nonlinear simulation analysis is carried out for the overall aseismic capacity of three-layer-frame structures with a compound metal damper. It is verified that a compound metal damper has better energy dissipation capacity and superior seismic performance, especially for a damper with double-objective optimized shape.

Synthesis of Novel 9-Fluoroanthracycline Derivatives

  • Rho, Young S.;박시호;Kim, Sun Y.;조인호;이철현;정채준;Kang, Heun S.
    • Bulletin of the Korean Chemical Society
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    • v.19 no.1
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    • pp.74-78
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    • 1998
  • Synthesis of novel 9-fluoroanthracyclines carrying L-fucose as a sugar component is described. Compound 3 containing a fluorine at the C-9 position was synthesized from an epoxide 2 and HF/Pyr (7 : 3). Bromination and hydrolysis of compound 3 resulted in synthesis of an aglycone, 9-fluoroanthracyclinone 6. The α-(1b) and β -anomers (1a) of the final product were obtained in high yields by a coupling reaction with the L-fucose.

A novel lanostane-type triterpene from Abies koreana

  • Kim, Hyun-Jung;Choi, Eun-Hwa;Lee, Ik-Soo
    • Proceedings of the PSK Conference
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    • 2003.10b
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    • pp.201.2-201.2
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    • 2003
  • A novel lanostane-type triterpene, (24E)-3,4-seco-9${\beta}$H-lanosta- 4(28),7,24- triene- 3,26- dioic acid was isolated from Abies koreana (Pinaceae) which is a tall evergreen tree grown indigenously in southern Korea. The structure of this compound was characterized by spectroscopic methods. Cytotoxicity of the compound was evaluated in vitro using the SRB method, and it showed marginal activity against human cancer cell lines.

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HQSAR Analysis on Novel series of 1-(4-Phenylpiperazin-1-yl-2-(1H-Pyrazol-1-yl) Ethanone Derivatives Targeting CCR1

  • Balasubramanian, Pavithra K.;Cho, Seung Joo
    • Journal of Integrative Natural Science
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    • v.6 no.3
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    • pp.163-169
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    • 2013
  • The chemokine receptor CCR1 a GPCR super family protein contains seven transmembrane domains. It plays an important role in rheumatoid arthritis, organ transplant rejection, Alzheimer's disease and also causes inflammation. Because of its role in disease processes, antagonism of CCR1 became an attractive therapeutic target. In the current study, we have taken a novel series of recently reported CCR1 antagonist of 1-(4-Phenylpiperazin-1-yl_-2-(1H-Pyrazol-1-yl) ethanone derivatives and performed a HQSAR analysis. The model was developed with Atom (A) and bond (B) parameters and with different set of atom counts to improve the model. The results of HQSAR showed good predictive ability in terms of $r^2$ (0.904) and $q^2$ (0.590) with 0.710 as standard error of prediction and 0.344 as standard error of estimate. The contribution map depicted the atom contribution in inhibitory effect. Compound-14 which was reported to be a highly active compound showed positive atom contribution in three R groups ($R^3$. $R^{5a}$ and $R^{2b}$) in inhibitory effect, which could be the reason why this compound is highly active compound whereas, the lowest active compound-6 showed negative contribution to inhibitory effect.

A New Compound Isolation and Structure Analysis from Phellodendron Amurense Fruit Extract (황벽나무 열매 추출물로부터 신규 화합물의 분리 및 구조분석)

  • Kim, Young-Hee;Choi, Jung Eun;Hong, Jin-Young;Jo, Chang Wook;Lee, Jeung-Min;Kim, Soo Ji
    • Journal of the Korean Wood Science and Technology
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    • v.41 no.4
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    • pp.269-275
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    • 2013
  • Antifungal and insecticidal activity of Korean traditional medicinal plants was carried out to develop natural material for the development of organic cultural heritage conservation. As a result, Phellodendron amurense fruit was finally selected as a candidate of antifungal and insecticidal natural material. An novel active compound was purified from the ethylacetate fraction of Phellodendron amurense fruits using silica gel and Sephadex LH-20 column chromatography and PTLC. The compound was obtained as yellow oil form; UV ${\lambda}_{max}$(MeOH): 260 nm. The chemical structure of novel compound was determined as (4'-ethyl-2'-methylfuranyl)-6-methoxy-7-methylnona-2E,4E,6Z,8E-tetraenoic acid on the basis of various NMR experiments including $^1H$- and $^{13}C$-NMR, HMQC, HMBC and ESI-mass spectrum.

Synthesis and Spectral Properties of Novel Thionaphtoquinone Dyes

  • Sayil, Cigdem;Ibis, Cemil
    • Bulletin of the Korean Chemical Society
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    • v.31 no.5
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    • pp.1233-1236
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    • 2010
  • 2,3-Dichloro-1,4-naphtoquinone 1 compound was reacted with octadecanethiol 2 in two different mole ratio. Compound 3 was obtained from the reaction of 1 and 2 in 1:2 mole/mole ratio. Compounds 7 and 8 were obtained from reaction of 1 and 2 in 1:1 mole/mole ratio and known compound 9 was synthesized as by-product in this reaction. Novel compounds 5a-e were obtained from reaction of 1 and related thiols 4a-e. Known compounds 6c and 6e were synthesized as by-product in this reaction. The structures of the compounds were characterized by elemental analysis, UV-vis, FTIR, $^1H$-NMR, $^{13}C$-NMR and Mass spectroscopies.

Synthesis and Properties of Novel Rhodamine 6G Fluorescent Dye Compound

  • Kim, Hyung-Joo;Wang, Sheng;Son, Young-A
    • Textile Coloration and Finishing
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    • v.24 no.3
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    • pp.153-157
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    • 2012
  • One of organic dye materials which have been long lasting investigated is rhodamine 6G dye series. This dye has been attracted with considerable interests due to the reason of its promising photochemical properties. In this study, a novel fluorescent dye compound based on rhodamine 6G derivative was synthesized through the reaction of rhodamine 6G hydrazide and indole-3-carboxaldehdyde. Absorption and fluorescent emission spectra of this dye were determined with the properties of solvatofluorochromism. Related electron energy states of the dye compound were also characterized by computational calculations.