1484-19-1Relevant articles and documents
Hydroxyindole-O-methyltransferase. I. Substrate binding.
Ho,McIsaac,Tansey
, p. 130 - 131 (1969)
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Conversion of 2-Halo-N-allylanilines to Indoles via Palladium(0) Oxidative Addition-Insertion Reactions
Odle, Roy,Blevins, Burke,Ratcliff, Matt,Hegedus, Louis S.
, p. 2709 - 2710 (1980)
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Monti,Schmidt
, p. 3331,3337 (1971)
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Horseradish peroxidase-mediated aerobic and anaerobic oxidations of 3-alkylindoles
Ling, Ke-Qing,Sayre, Lawrence M.
, p. 3543 - 3551 (2005)
Little is known about the HRP-mediated oxidations of 3-alkylindoles. Whereas 3-methylindole and 3-ethylindole were found to be turned over smoothly by HRP, reactions of tryptophol and N-acetyltryptamine were inefficient. Oxidations of the former two indoles by HRP under aerobic conditions led to the corresponding ring-opened o-acylformanilides and oxindoles, whereas anaerobic oxidations resulted in oxidative dimerization. The major products of anaerobic oxidation of 3-methylindole were shown to be two hydrated dimers, while anhydrodimers were obtained in the 3-ethyl case. The proposed mechanism involves HRP-mediated one-electron oxidation to give an indole radical that either dimerizes (anaerobic conditions) or reacts with O2 (aerobic conditions). Measured kinetics of indole oxidation by HRP compounds I and II mirrored their relative reactivities under turnover conditions. The observed comparable binding affinities for all four indole substrates investigated suggest that the low reactivity of tryptophol and N-acetyltryptamine reflect binding to HRP in an orientation that is disadvantageous to electron transfer oxidation of the indole ring.
Synthesis of DPIE [2-(1,2-Diphenyl-1H-indol-3-yl)ethanamine] Derivatives and Their Regulatory Effects on Pro-Inflammatory Cytokine Production in IL-1β-Stimulated Primary Human Oral Cells
Jung, Seunggon,Kim, Eunae,Lee, Sunwoo,Lee, Tae-Hoon,Lim, Jeongah,Seong, Jihyoun
, (2022/02/02)
Interleukin-1 beta (IL-1β) has diverse physiological functions and plays important roles in health and disease. In this report, we focus on its function in the production of pro-inflammatory cytokines, including IL-6 and IL-8, which are implicated in several autoimmune diseases and host defense against infection. IL-1β activity is markedly dependent on the binding affinity toward IL-1 receptors (IL-1Rs). Several studies have been conducted to identify suitable small molecules that can modulate the interactions between 1L-1β and 1L-1R1. Based on our previous report, where DPIE [2-(1,2-Diphenyl-1H-indol-3-yl)ethanamine] exhibited such modulatory activity, three types of DPIE derivatives were synthesized by introducing various substituents at the 1, 2, and 3 positions of the indole group in DPIE. To predict a possible binding pose in complex with IL-1R1, a docking simulation was performed. The effect of the chemicals was determined in human gingival fibroblasts (GFs) following IL-1β induction. The DPIE derivatives affected different aspects of cytokine production. Further, a group of the derivatives enabled synergistic pro-inflammatory cytokine production, while another group caused diminished cytokine production compared to DPIE stimulation. Some groups displayed no significant difference after stimulation. These findings indicate that the modification of the indole site could modulate IL-1β:IL1R1 binding affinity to reduce or enhance pro-inflammatory cytokine production.
KOH-mediated stereoselective alkylation of 3-bromooxindoles for the synthesis of 3,3′-disubstituted oxindoles with two contiguous all carbon quaternary centres
Devi, Manju,Jadhav, Amol P.,Singh, Ravi P.
, p. 8445 - 8448 (2021/05/25)
The stereoselective synthesis of 3,3′-disubstituted oxindoles having all-carbon quaternary stereocenters has been achieved using KOH as a base with an excellent diastereomeric ratio (98?:?2). The practicability of the present methodology has been validated with the synthesis of a series of substrates in good to excellent yields. The aesthetic simplicity, accessibility, and eco-friendly base (KOH) have prompted the broader application of the present methodology in organic synthesis.
Compound containing indole ring structure, preparation method and application of compound, and bactericide
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Paragraph 0080; 0085; 0086; 0087, (2021/07/31)
The invention belongs to the field of pesticides and discloses a compound containing an indole ring structure, a preparation method and application of the compound and a bactericide. The compound has the structure shown in the formula (I), and the compound has an excellent prevention and treatment effect on cucumber downy mildew, is equivalent to the current commercial oomycete disease prevention and treatment agent oxathiapiprolin, and has a good market development prospect.