59-48-3Relevant articles and documents
Oxidation of indole with CPO and GOx immobilized on mesoporous molecular sieves
Jung, Dirk,Hartmann, Martin
, p. 378 - 383 (2010)
Green chemistry and environmentally benign reaction engineering play an important role for future industrial processes. It is expected that the number of chemical reactions carried out via enzymatic catalysis will increase strongly. To achieve this aim, stable (viz. leaching and deactivation is prevented) heterogeneous biocatalysts are required. In this study, cross-linked enzyme aggregates of chloroperoxidase were grown in large-pore mesocellular foams (MCF). By changing the various synthesis parameters, the specific activity and the effective activity (viz. the enzyme activity units per mmol of adsorbed enzyme) are improved. The resulting biocatalysts composed of cross-linked chloroperoxidase and cross-linked glucose oxidase were tested in the oxidation of indole. The catalytic test under continuous operation conditions in a fixed-bed reactor confirmed that the cross-linked enzymes are less prone to leaching compared to the physically adsorbed enzymes in the pores of MCF or SBA-15.
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Gassmann,van Bergen
, p. 2718 (1973)
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Paramagnetic nuclear magnetic resonance relaxation and molecular mechanics studies of the chloroperoxidase-indole complex: Insights into the mechanism of chloroperoxidase-catalyzed regioselective oxidation of indole
Zhang, Rui,He, Qinghao,Chatfield, David,Wang, Xiaotang
, p. 3688 - 3701 (2013)
To unravel the mechanism of chloroperoxidase (CPO)-catalyzed regioselective oxidation of indole, we studied the structure of the CPO-indole complex using nuclear magnetic resonance (NMR) relaxation measurements and computational techniques. The dissociation constant (KD) of the CPO-indole complex was calculated to be approximately 21 mM. The distances (r) between protons of indole and the heme iron calculated via NMR relaxation measurements and molecular docking revealed that the pyrrole ring of indole is oriented toward the heme with its 2-H pointing directly at the heme iron. Both KD and r values are independent of pH in the range of 3.0-6.5. The stability and structure of the CPO-indole complex are also independent of the concentration of chloride or iodide ion. Molecular docking suggests the formation of a hydrogen bond between the NH group of indole and the carboxyl O of Glu 183 in the binding of indole to CPO. Simulated annealing of the CPO-indole complex using r values from NMR experiments as distance restraints reveals that the van der Waals interactions were much stronger than the Coulomb interactions in the binding of indole to CPO, indicating that the association of indole with CPO is primarily governed by hydrophobic rather than electrostatic interactions. This work provides the first experimental and theoretical evidence of the long-sought mechanism that leads to the "unexpected" regioselectivity of the CPO-catalyzed oxidation of indole. The structure of the CPO-indole complex will serve as a lighthouse in guiding the design of CPO mutants with tailor-made activities for biotechnological applications.
Transition-metal-catalyzed electrophilic activation of 1,1-difluoro-1- alkenes: Oxindole synthesis via intramolecular amination
Tanabe, Hiroyuki,Ichikawa, Junji
, p. 248 - 249 (2010)
In the presence of a catalytic amount of palladium(II) chloride, β,β-difluorostyrenes bearing a sulfonamido group at the ortho position were treated with trimethylsilyl trifluoro-methanesulfonate to afford oxindoles in high yield. The reactions proceeded via 5-endo-trig cyclization, hydrolysis, and desulfonylation. This sequence allowed the transformation of difluorostyrenes into free oxindoles in a one-pot operation.
Green method for preparing oxindole derivative
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Paragraph 0027-0029, (2021/06/26)
The invention relates to the technical field of green organic synthesis, and provides a green method for preparing oxindole derivatives, which comprises the following steps: taking indole compounds with different functional groups as raw materials, under the conditions of room temperature, opening and neutral, adopting MBrx (M is Fe,Fe,Ce and the like) as a catalyst with X equal to 2 or 3, and adopting hydrogen peroxide as a sole oxidant to generate active bromine (RBS) in situ, and catalytically synthesizing the oxindole derivative. According to the method disclosed by the invention, MBrx (such as FeBr2, CeBr3 and the like) is used as the catalyst, so that an expensive or complex catalyst is avoided, and the method is green, environment-friendly, safe, simple, efficient, mild in reaction condition and wide in substrate application range, has a relatively good application prospect and is expected to be widely applied to organic synthesis, fine chemical engineering and pharmaceutical industry.
Design, synthesis, and in vitro and in vivo anti-angiogenesis study of a novel vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitor based on 1,2,3-triazole scaffold
Wang, De-pu,Liu, Kai-li,Li, Xin-yang,Lu, Guo-qing,Xue, Wen-han,Qian, Xin-hua,Mohamed O, Kamara,Meng, Fan-hao
, (2020/12/21)
In the past five years, our team had been committed to click chemistry research, exploring the biological activity of 1,2,3-triazole by synthesizing different target inhibitors. In this study, a series of novel indole-2-one derivatives based on 1,2,3-triazole scaffolds were synthesized for the first time, and their inhibitory activity on vascular endothelial growth factor receptor-2 (VEGFR-2) was tested. Most of the compounds had shown promising activity in the VEGFR-2 kinase assay and had low toxicity to human umbilical vein endothelial cells (HUVECs). The compound 13d (IC50 = 26.38 nM) had better kinase activity inhibition ability than sunitinib (IC50 = 83.20 nM) and was less toxic to HUVECs. Moreover, it had an excellent inhibitory effect on HT-29 and MKN-45 cells. On the one hand, by tube formation assay, transwell, and Western blot analysis, compound 13d could inhibit VEGFR-2 protein phosphorylate on HUVECs, thereby inhibiting HUVECs migration and tube formation. In vivo study, the zebrafish model with VEGFR-2 labeling also verified that compound 13d had more anti-angiogenesis ability than sunitinib. On the other hand, molecular docking and molecular dynamics (MD) simulation results showed that compound 13d could stably bind to the active site of VEGFR-2. Based on the above findings, compound 13d could be considered an effective anti-angiogenesis drug and has more development value than sunitinib.