1968-05-4Relevant articles and documents
Cooperative Cation-Binding Catalysis as an Efficient Approach for Enantioselective Friedel–Crafts Reaction of Indoles and Pyrrole
Kim, Mun Jong,Xue, Lu,Liu, Yidong,Paladhi, Sushovan,Park, Si Joon,Yan, Hailong,Song, Choong Eui
, p. 811 - 823 (2017)
In this study, we demonstrated the cooperative cation-binding catalysis as an efficient approach for enantioselective Friedel–Crafts reaction of indoles and pyrroles. By using highly accessible chiral oligoethylene glycol (oligoEG) as the cation-binding catalyst and KF as the base, a highly enantioselective Friedel–Crafts reaction of indoles, 4,7-dihydroindoles, and pyrrole with bench-stable α-amidosulfones as in-situ equivalents of sensitive imines was achieved. The scope of this new catalytic protocol was not limited to aromatic imines. Heteroaromatic and aliphatic substrates as well as α-iminoethyl glyoxylate also afforded the desired products with excellent yields and ees. The enforced proximity of the catalyst and substrates in a chiral cage in situ formed by incorporation of the potassium salt enhanced the reactivity and efficiently transferred the stereochemical information, mimicking the action of enzymes. (Figure presented.).
Synthesis and antibacterial evaluation of 3,3′-diindolylmethane derivatives
Roy, Sutapa,Gajbhiye, Rahul,Mandal, Madhumita,Pal, Churala,Meyyapan, Arumugam,Mukherjee, Joydeep,Jaisankar, Parasuraman
, p. 1371 - 1377 (2014)
Various 3,3′-diindolylmethane (DIM) derivatives were synthesized and the antibacterial activity of these compounds were tested against ten bacterial strains and their minimum inhibitory concentration (MIC) values were determined. The MIC values of derivatives 3a-d and 5a-e were ranging from 125 to 500 μg/mL. Among these derivatives, 2-(di(1H-indol-3-yl)methyl)phenol (5a) and 3-((1H-indol-3-yl)(pyridin-3-yl)methyl)-1H-indole (5d) exhibited potent activity, showing MIC values 6.5-62.5 μg/mL against Gram positive and Gram negative bacteria. Hemolytic assay of these active DIM derivatives did not show considerable toxic effect on the normal human erythrocytes.
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Beteiller,Colilla
, p. 3393,3402 (1972)
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N-Allylation And N-Benzylation Of 2-Phenylindole And Its Condensation With Carbonyl Compounds
Obynochnyi, A. A.,Anisimov, B. N.,Sergeeva, N. D.,Prostakov, N. S.
, p. 553 - 555 (1993)
By allylation and benzylation of 2-phenyl- and 2-phenyl-3-formylindole, N-allyl- and benzyl-substituted indoles have been obtained.By condensation of 2-phenylindole with 2-formylfluorene, and also with 4-aza- or 3-methyl-2-azafluorenone, compounds containing fragments of the indole, fluorene, and azafluorenone systems have been synthesized.In the interaction of 2-phenylindole or indole with formaldehyde and 2,5-dimethylpiperidin-4-one, depending on the temperature, bis(2-phenylindol-3-yl)methane, (2',5'-dimethyl-4'-oxopiperidino)-(1-indolyl)methane, andbis(indol-3-yl)methane are formed.
A Novel Electrochemical Oxidation Reactions Utilizing Cyclodextrins. Anodic Oxidation of Indole-Cyclodextrin-Alcohol System
Suda, Kohji,Takanami, Toshikatsu
, p. 1915 - 1916 (1994)
The anodic oxidation of indoles (1) and alcohols (2) in the presence of cyclodextrins gave diindolylmethanes in good yields.Cyclic voltammetry and macro scale electrolyses showed that the reaction was initiated by the oxidation of 2 with an oxidation potential higher than that of 1.
Decarboxylative Coupling Reaction of 2-(1H-Indol-3-yl)acetic Acids with Indole, Azaindole, Benzimidazole and Indazole Derivatives
Pillaiyar, Thanigaimalai,Uzair, Muhammad,Ullah, Saif,Schnakenburg, Gregor,Müller, Christa E.
, p. 4286 - 4293 (2019)
3,3′-Diindolylmethanes (DIMs) are an important class of indole alkaloids that exhibit anti-inflammatory and anti-cancer effects. Herein, we report on a new, mild and efficient copper(II)-promoted decarboxylative coupling reaction of 2-(1H-indol-3-yl)acetic acid derivatives (1 a–h) with a variety of (substituted) indoles (2 a–t) yielding (un)symmetrically substituted DIMs (3 a–z, 3 aa–ai). Reaction of 2-(1H-indol-3-yl)acetic acid (1 a) with 7-azaindole led to the 3,3′-connected DIM analog 5 d, while 4-, 5-, and 6-azaindoles and benzimidazole reacted at the N1-nitrogen atom. Reaction of 1 a with 1H-indazoles led to a mixture of 1- and 2-substituted indazole derivatives. The new method allows large-scale synthesis of biologically active DIMs. (Figure presented.).
Convenient synthesis of 5,6,11,12,17,18-hexahydrocyclononal[1,2-b:4,5-b′:7,8-b″] triindole, a Novel phytoestrogen
Staub, Richard E.,Bjeldanes, Leonard F.
, p. 167 - 169 (2003)
An efficient one-pot synthesis is described of 5,6,11,12,17,18-hexahydrocyclononal[1,2-b:4,5-b':7,8-b ]triindole (CTr), a potent estrogen agonist from food plants. For the procedure, gramine is treated with dimethyl sulfate and sodium in ethanol at room temperature. Quenching of the reaction with water and workup of the product provides CTr in approximately 75% yield.
Palladium catalyzed alkylation of indole via aliphatic C-H bond activation of tertiary amine
Ramachandiran,Muralidharan,Perumal
, p. 3579 - 3583 (2011)
Alkylation of indoles has been achieved via Pd-catalyzed aliphatic C-H bond activation of tertiary amine coupling with indole followed by C-N bond cleavage and subsequent addition of indole. This method involves the migration of alkane chain from tertiary amine to indole.
Minor bioactive indoles from kimchi mirror the regioselectivity in indole-3-carbinol oligomerization
Cheng Qian, Jia,Jing Zhu, Wen,Liu, Dan,Ping Lin, Li,Xiang Tan, Ren
, (2022/03/07)
Kimchi is a globally consumed food with diverse health-benefits, but the low-abundance bioactive compounds in kimchi remain largely neglected. Here we show that kimchi contains a family of low-abundance (0.5–1.6 μg/g, dried weight) high-order indole oligomers derived from indole-3-carbinol (I3C), a breakdown product released from cruciferous vegetables used for producing the traditional subsidiary food. The structure determination of such complex molecules was accomplished by synthesizing linear indole oligomers as standard materials followed by the LC–HR–MS analysis. One indole tetramer (LTe2) is substantially toxic to tumor MV4-11 (IC50 = 1.94 μM) and THP-1 cells (IC50 = 7.12 μM). Collectively, the work adds valuable information to the knowledge package about kimchi, and may inspire the generation of indole-based molecules, to which many drugs belong.
Preparation of G-CuO NPs and G-ZnO NPs with mallow leaves, investigation of their antibacterial behavior and synthesis of bis(indolyl)methane compounds under solvent-free microwave assisted dry milling conditions using G-CuO NPs as a catalyst
SULAK, Mine
, p. 1517 - 1532 (2021/10/26)
In this study, biogenic copper and zinc oxide nanoparticles (G-ZnONPs and G-CuONPs) were synthesized by the green synthesis method using Malva parviflora L. (Millow) leaf extract and the obtained nanoparticles were characterized in detail with UV-Vis, FTIR, SEM, XRD. The antibacterial properties of the synthesized nanoparticles on gram-positive and gram-negative bacteria were investigated and it was found that the nanoparticles had high antimicrobial activity in the results of the experiments. With the obtained G-CuONPs, the synthesis of bis(indolyl)methanes with the "green" one-pot synthesis using microwave was achieved quickly and with high efficiency, and the thermal behavior of the obtained products was investigated.
