Indole synthesis: a review and proposed classification

The present disclosure relates to compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

Hepatitis C virus inhibitors

Highly invasive tumor cells are characterized by a metabolic switch, known as the Warburg effect, from “normal” oxidative phosphorylation to increased glycolysis even under sufficiently oxygenated conditions. This dependence on glycolysis also confers a growth advantage to cells present in hypoxic regions of the tumor. One of the key enzymes involved in glycolysis, the muscle isoform of lactate dehydrogenase (LDH-A), is overexpressed by metastatic cancer cells and is linked to the vitality of tumors in hypoxia. This enzyme may be considered as a potential target for new anticancer agents, since its inhibition cuts cancer energetic and anabolic supply, thus reducing the metastatic and invasive potential of cancer cells. We have discovered new and efficient N-hydroxyindole-based inhibitors of LDH-A, which are isoform-selective (over LDH-B) and competitive with both the substrate (pyruvate) and the cofactor (NADH). The antiproliferative activity of these compounds was confirmed on a series of cancer cell lin...

Discovery of N-hydroxyindole-based inhibitors of human lactate dehydrogenase isoform A (LDH-A) as starvation agents against cancer cells.

Elimination of suitable leaving groups from 3-substituted indoles under basic or acidic conditions readily provides alkylideneindolenine intermediates that may react with a large variety of nucleophilic reagents. This article highlights some recent developments of this synthetic approach for the preparation of functionalized indole derivatives.

Synthesis of 3-substituted indoles via reactive alkylideneindolenine intermediates

Chemistry of α-oxoesters: a powerful tool for the synthesis of heterocycles.

New synthetic technology for the construction of N-hydroxyindoles and synthesis of nocathiacin I model systems

Synthesis of Highly Substituted N-Hydroxyindoles through 1,5-Addition of Carbon Nucleophiles to In Situ Generated Unsaturated Nitrones†

A new synthetic method providing expedient access to a wide range of polyfunctionalized N-hydroxyindoles (IV) is reported. These unique constructs are assembled by nucleophilic additions to in situ generated α,β-unsaturated nitrones (III) through carbon–carbon and carbon–heteroatom bond formation. The new synthetic technology was applied to the synthesis of nocathiacin I (1) model systems (2 and 3a–c) containing the N-hydroxyindole structural motif.

New Synthetic Technology for the Construction of N‐Hydroxyindoles and Synthesis of Nocathiacin I Model Systems.

Tuning siRNA Specificity through Seed Region Incorporation of Deoxyribonucleotide Stereoisomers

Synthesis of Highly Substituted N‐Hydroxyindoles Through 1,5‐Addition of Carbon Nucleophiles to in situ Generated Unsaturated Nitrones.

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