• Title/Summary/Keyword: Oxindoles

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An Expedient Synthesis of Oxindole Dimers by Direct Oxidative Dimerization of Oxindoles

  • Lee, Hyun Ju;Lee, Sangku;Lim, Jin Woo;Kim, Jae Nyoung
    • Bulletin of the Korean Chemical Society
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    • v.34 no.8
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    • pp.2446-2450
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    • 2013
  • Oxindole dimers have been used as intermediates in the synthesis of various cyclotryptamine alkaloids. An efficient direct synthesis of oxindole dimers has been carried out from 3-substituted oxindoles via an oxidative dimerization using manganese(III) acetate or copper acetate/silver acetate system.

Synthesis of Oxindole and Isatin Derivatives (옥시인돌과 이사틴 유도체들의 합성)

  • Kim, Byung-SO
    • Journal of the Korean Society of Industry Convergence
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    • v.6 no.2
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    • pp.123-129
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    • 2003
  • Oxindoles(6a-g) are obtained by rhodium(II)-catalyzed Wolff rearrangement of diazoquinolinediones in moderate yields. Treatment of 6a-g oxindole derivatives reacted with CAN in acetonitrile at room temperature to gave 7a-g isatins in good yields. The structures of these compound were identified by MP, IR and NMR-spectra.

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Deuterium-labeling Toward Robust Function of Organic Molecules: Enhanced Photo-stability of Partially Deuterated 1', 3', 3'-Trimethyl-6-nitrospiro[2H-1- benzopyran-2, 2'-indoline]

  • Kawanishi, Yuji;Inoue, Kyoko;Ohta, Shin-Ichi;Miyazawa, Akira
    • Rapid Communication in Photoscience
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    • v.3 no.4
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    • pp.64-66
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    • 2014
  • Synthesis of a deuterium-labeled derivative of nitrospirobenzopyran (NSP), one of representative photochromic compounds, has been described. Four deuteriums were successfully introduced on 1-methyl and ${\alpha}$-methyne relative to spiro-carbon in the title compound with more than 95atom%D purity. Main photodegraded products of NSP were two oxindoles in acetonitrile, and additional products were formed in poly(isobutyl-methacrylate) films possibly due to restricted molecular motion in polymer matrix. Quantitative HPLC analysis revealed that partial introduction of deuterium to NSP brought a noticeable isotope effect, recognizable enhancement in photo-resistivity of NSP, i.e.,8.3% in solutions and 29% in polymeric films.

RK-270D and E, Oxindole Derivatives from Streptomyces sp. with Anti-Angiogenic Activity

  • Jang, Jun-Pil;Jang, Mina;Nogawa, Toshihiko;Takahashi, Shunji;Osada, Hiroyuki;Ahn, Jong Seog;Ko, Sung-Kyun;Jang, Jae-Hyuk
    • Journal of Microbiology and Biotechnology
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    • v.32 no.3
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    • pp.302-306
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    • 2022
  • A chemical investigation of a culture extract from Streptomyces sp. RK85-270 led to the isolation and characterization of two new oxindoles, RK-270D (1) and E (2). The structures of 1 and 2 were determined by analyzing spectroscopic and spectrometric data from 1D and 2D NMR and High-resolution electrospray ionization mass spectrometry (HRESIMS) experiments. Compound 1 exhibited anti-angiogenic activities against human umbilical vein endothelial cells (HUVECs) without cytotoxicity. Results of Western blot analysis revealed that 1 inhibits VEGF-induced angiogenesis in the HUVECs via VEGFR2/ p38 MAPK-mediated pathway.