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HETEROGENEOUS-CATALYTIC FISCHER REACTION. 13. CATALYTIC SYNTHESIS OF 4-, 5-, 6-, AND 7-METHOXYINDOLES

Methoxy-substituted acetaldehyde phenylhydrazones were cyclized in the vapor phase on GIPKh-115 catalyst to give 4-, 5-, 6-, and 7-methoxyindoles. 5-Methoxyindole was obtained in 50percent yield, 4- and 6-methoxyindoles were obtained in 85percent yield, and 7-methoxyindole was obtained in 45percent yield.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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USE OF DERIVATIVES OF INDOLES FOR THE TREATMENT OF CANCER

The present invention relates to the use of derivatives of indoles having a general formula (I) as follow: for the manufacture of a pharmaceutical composition intended for the treatment of cancer.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Meta-selective substitution of phenols with indoles via one-pot oxidative dearomatization-Michael addition-aromatization

An oxidative coupling strategy involving hypervalent organoiodine-induced oxidative dearomatization of 4-substituted phenols, Bronsted acid catalyzed Michael addition with indoles, and aromatization has been developed. The one-pot reaction provides an efficient access to the meta-indole-substituted phenol derivatives. Georg Thieme Verlag Stuttgart ¡¤ New York.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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PIII-Chelation-Assisted Indole C7-Arylation, Olefination, Methylation, and Acylation with Carboxylic Acids/Anhydrides by Rhodium Catalysis

Rhodium-catalyzed C7-selective decarbonylative arylation, olefination, and methylation of indoles with carboxylic acids or anhydrides by C?H and C?C bond activation have been developed. Furthermore, C7-acylation products can also be generated selectively at a lower reaction temperature in the developed system. The key to the high reactivity and regioselectivity of this transformation is the appropriate choice of an indole N-PtBu2 chelation-assisted group. This method has many advantages, including easy access and removal of the directing group, the use of cheap and widely available coupling agents, no requirement of an external ligand or oxidant, a broad substrate scope, high efficiency, and the formation of a sole regioisomer.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Synthesis of (Z)-1-benzylidene-3-(1H-indol-1-yl)-1H-indene-2,2(3H)- dicarbonitriles via three-component reaction of 2-alkynylbenzaldehyde, malononitrile, and indole

Three-component reaction of 2-alkynylbenzaldehyde, malononitrile, and indole under mild conditions is described, which generates the desired (Z)-1-benzylidene-3-(1H-indol-1-yl)-1H-indene-2,2(3H)-dicarbonitriles in moderate to good yields. This reaction proceeds smoothly with high selectivity. The tandem condensation, nucleophilic addition, and 5-exo-cyclization may be involved in the process.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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A consecutive one-pot two-step approach to novel trifluoromethyl-substituted bis(indolyl)methane derivatives promoted by Sc(OTf)3 and p-TSA

A one-pot two-step reaction of 3-(trifluoroacetyl)coumarin and indole afforded trifluoromethyl-substituted bis(indolyl)methane compounds containing coumarin skeleton. The atomic economic and simply manipulative reaction involved premier treatment of reaction mixtures with Sc(OTf)3, followed by p-TSA in one-pot process. The reaction proceeded to give the title compounds in high yields (up to 95% yield).

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Acyl Phosphonates: Good hydrogen bond acceptors and ester/amide equivalents in asymmetric organocatalysis

This study demonstrates that unsaturated acyl phosphonates are excellent hydrogen-bond acceptors in enantioselective organocatalysis. By employing chiral thioureas orsquaramides as catalysts, the acyl phosphonates are effectively coordinated and activated by hydrogen bonding, thereby providing successful relay of the chirality from the catalyst to the substrate. A variety of highly stereoselective conjugate additions to alpha,beta-unsaturated acyl phosphonates were performed, using different carbon-based nucleophiles such as oxazolones, indoles, and 1,3-dicarbonyl compounds. The reaction concept has been developed to be a double nucleophilic reaction, and it is shown that the acyl phosphonates serve as masked ester or amide equivalents, which upon quenching with the second nucleophile generate the parent structures in situ. Accordingly, formal C-C bond formation reactions of ester and amide substrates are achieved, affording a broad spectrum of optically active conjugate adducts in good yields and excellent enantioselectivities. Based on the experimental results, the mechanisms for the different reactions are discussed, including the approach of the oxazolones, indoles, and 1,3-dicarbonyl compounds to the acyl phosphonate coordinated to the catalyst and the role of the catalyst for the reaction course of the nucleophiles.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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Inhibitors of HIV-1 attachment. Part 2: An initial survey of indole substitution patterns

The effects of introducing simple halogen, alkyl, and alkoxy substituents to the 4, 5, 6 and 7 positions of 1-(4-benzoylpiperazin-1-yl)-2-(1H-indol-3-yl)ethane-1,2-dione, an inhibitor of the interaction between HIV gp120 and host cell CD4 receptors, on activity in an HIV entry assay was examined. Small substituents at C-4 generally resulted in increased potency whilst substitution at C-7 was readily tolerated and uniformly produced more potent HIV entry inhibitors. Substituents deployed at C-6 and, particularly, C-5 generally produced a modest to marked weakening of potency compared to the prototype. Small alkyl substituents at N-1 exerted minimal effect on activity whilst increasing the size of the alkyl moiety led to progressively reduced inhibitory properties. These studies establish a basic understanding of the indole element of the HIV attachment inhibitor pharmacophore.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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A method for methylation reaction (by machine translation)

The invention relates to a method for methylation reaction. Characterized in that includes: a reaction substrate in the organic solvent, trifluoroacetic acid methyl ester as a methylation reagent, in the presence of an alkali reaction, to obtain the corresponding methylation product. The invention opens up a new methylation method, the process is low priced, simple and convenient operation, mild reaction conditions, substrate and wide range of application, to avoid the use of dimethyl sulfate, methyl iodide and the like and toxic chemicals methylation reagent, can receive higher yield of methylation product. (by machine translation)

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

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An Orally Bioavailable, Indole-3-glyoxylamide Based Series of Tubulin Polymerization Inhibitors Showing Tumor Growth Inhibition in a Mouse Xenograft Model of Head and Neck Cancer

A number of indole-3-glyoxylamides have previously been reported as tubulin polymerization inhibitors, although none has yet been successfully developed clinically. We report here a new series of related compounds, modified according to a strategy of reducing aromatic ring count and introducing a greater degree of saturation, which retain potent tubulin polymerization activity but with a distinct SAR from previously documented libraries. A subset of active compounds from the reported series is shown to interact with tubulin at the colchicine binding site, disrupt the cellular microtubule network, and exert a cytotoxic effect against multiple cancer cell lines. Two compounds demonstrated significant tumor growth inhibition in a mouse xenograft model of head and neck cancer, a type of the disease which often proves resistant to chemotherapy, supporting further development of the current series as potential new therapeutics.

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Reference£º
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles