872030-46-1

Usage

Structure

1H-Indole-2-carboxylic acid derivative with a fluorine substitution at the 5th position and a phenylmethoxy group at the 6th position

Type

Methyl ester

Potential pharmaceutical applications

Yes

Biological activities

Unknown, but may exhibit various activities

Use as a starting material in organic synthesis

Yes

Safety precautions

Should be handled and used with appropriate precautions and under the guidance of trained professionals.

Upstream product

• 175968-61-3 3-fluoro-4-[(phenylmethyl)oxy]benzaldehyde 
• 1816-92-8 Methyl azidoacetate 

Downstream Products

• 1179983-85-7 6-(benzyloxy)-5-fluoro-1H-indole 
• 1179983-84-6 6-(benzyloxy)-5-fluoro-1H-indole-2-carboxylic acid 

Relevant academic research and scientific papers

5-Hydroxyindole-2-carboxylic acid amides: Novel histamine-3 receptor inverse agonists for the treatment of obesity

Obesity is a major risk factor in the development of conditions such as hypertension, hyperglycemia, dyslipidemia, coronary artery disease, and cancer. Several pieces of evidence across different species, including primates, underscore the implication of the histamine 3 receptor (H3R) in the regulation of food intake and body weight and the potential therapeutic effect of H3R inverse agonists. A pharmacophore model, based on public information and validated by previous investigations, was used to design several potential scaffolds. Out of these scaffolds, the 5-hydroxyindole-2-carboxylic acid amide appeared to be of great potential as a novel series of H3R inverse agonist. Extensive structure-activity relationships revealed the interconnectivity of microsomal clearance and hERG (human ether-a-go-go-related gene) affinity with lipophilicity, artificial membrane permeation, and basicity. This effort led to the identification of compounds reversing the (R)-R-methylhistamine-induced water intake increase in Wistar rats and, further, reducing food intake in diet-induced obese Sprague-Dawley rats. Of these, the biochemical, pharmacokinetic, and pharmacodynamic characteristics of (4,4-difluoropiperidin- 1-yl)[1-isopropyl-5-(1-isopropylpiperidin-4-yloxy)-1H-indol-2-yl]-methanone 36 are detailed.

INDOLE DERIVATIVES AS HISTAMINE RECEPTOR ANTAGONISTS

The present invention relates to compounds of formula (I) wherein X, R1, R2, R3, R4 and R5 are as defined in the description and claims, and pharmaceutically acceptable salts thereof, to the preparati