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.).
The cruciferous phytoalexins rapalexin A, brussalexin A and erucalexin: Chemistry and metabolism in Leptosphaeria maculans
Pedras, M. Soledade C.,Sarma-Mamillapalle, Vijay K.
, p. 3991 - 3996 (2012)
The interactions of the cruciferous phytoalexins rapalexin A (1), brussalexin A (2) and erucalexin (3) with the fungal plant pathogen Leptosphaeria maculans were analyzed and their inhibitory activities against this pathogen were determined. The reaction of L. maculans to N-methyl S-(indolyl-3-methyl)carbamodithioate, an analogue of brussalexin A, was also investigated. Rapalexin A was resistant to metabolism and was the most inhibitory of all compounds tested, suggesting that increasing concentrations of rapalexin A in Brassica species would improve their disease resistance to L. maculans. By contrast, erucalexin was quickly detoxified by reduction to yield 3-dihydroerucalexins. The relative configurations of the diastereomeric mixture of dihydroerucalexins were established by 1D 1H nuclear Overhauser enhancement spectroscopy (NOE). Brussalexin A was chemically unstable decomposing mainly to indolyl-3-methanol, a product with anti-cancer properties. For this reason, brussalexin A might be of interest to use as a prodrug.
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.
Direct use of methanol as an alternative to formaldehyde for the synthesis of 3, 3′-bisindolylmethanes (3, 3′-BIMs)
Sun, Chunlou,Zou, Xiaoyuan,Li, Feng
, p. 14030 - 14033 (2013)
The article examines the direct use of methanol as an alternative to formaldehyde for the synthesis of 3,3'-Bisindolylmethanes (3,3'-BIM). The use of abundant and renewable feedstock reagents to construct C-C bonds, the essential link in all organic molecules, represents one of the most central subjects. Methanol, the simplest alcohol, can be made from fossil fuels, such as natural gas and coal, renewable resources, such as biomass and landfill gas, and carbon dioxide from the atmosphere. The catalytic dehydrogenation of methanol was regarded as the crucial step for such transformation. Very recently, Beller and co-workers demonstrated ruthenium-catalyzed dehydrogenation of methanol to hydrogen and C1 residuals.
InCl3-HMTA as a methylene donor: One-pot synthesis of diindolylmethane (DIM) and its derivatives
Pradhan, Prasun K.,Dey, Sumit,Giri, Venkatachalam Sesha,Jaisankar, Parasuraman
, p. 1779 - 1782 (2005)
Treatment of indoles la-k with hexamethylenetetramine (HMTA) (2) in presence of a catalytic amount (10 mol%) of InCl3 resulted in 3,3′-diindolylmethane (DIM) derivatives 3a-k in excellent yields. Georg Thieme Verlag Stuttgart.
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.
Eco-friendly synthesis and study of new plant growth promoters: 3,3′-Diindolylmethane and its derivatives
Pal, Churala,Dey, Sumit,Mahato, Sanjit Kumar,Vinayagam, Jayaraman,Pradhan, Prasun K.,Giri, Venkatachalam Sesha,Jaisankar, Parasuraman,Hossain, Tanvir,Baruri, Shikhi,Ray, Debjit,Biswas, Suparna Mandal
, p. 4924 - 4928 (2007)
3,3′-Diindolylmethane (DIM) derivatives 3a-k, prepared in one-pot from indoles 1a-k and hexamethylenetetramine (2) using ionic liquid [Bmim]BF4 as eco-friendly recyclable solvent as well as catalyst, showed good plant growth promoting activity on Oryza sativa. Among the DIM derivatives synthesized 3c shows potent auxin like growth promoting activity.
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.
