230646-11-4

Usage

Molecular structure

1H-Pyrrole-2-carboxylic acid, 3-amino-4,5-dimethyl-, ethyl ester (9CI) consists of a pyrrole ring with a carboxylic acid and an amino group attached to the 3rd and 4th carbon atoms, and a methyl group attached to the 4th and 5th carbon atoms. The ethyl group is attached to the carboxylic acid, forming an ethyl ester.

Chemical class

The compound belongs to the pyrrole class of organic compounds.

Functional groups

The compound contains a pyrrole ring, a carboxylic acid, an amino group, and an ethyl ester.

Potential applications

1H-Pyrrole-2-carboxylic acid, 3-amino-4,5-dimethyl-, ethyl ester (9CI) has potential applications in the field of organic synthesis and medicinal chemistry.

Use as a building block

The compound can be used as a building block for the synthesis of various pharmaceuticals and bioactive molecules.

Biological and pharmacological properties

The compound exhibits interesting biological and pharmacological properties, making it a valuable compound in drug discovery and development.

Upstream product

• 4468-47-7 2-methyl-3-oxo-butyronitrile 

Downstream Products

• 230646-12-5 Ethyl (E)-3-(cinnamoylamino)-4,5-dimethylpyrrole-2-carboxylate 

Relevant academic research and scientific papers

Structure-Activity Relationship Studies of Pyrimido[5,4-b]indoles as Selective Toll-Like Receptor 4 Ligands

Previous high throughput screening studies led to the discovery of two novel, nonlipid-like chemotypes as Toll-like receptor 4 (TLR4) agonists. One of these chemotypes, the pyrimido[5,4-b]indoles, was explored for structure-activity relationship trends relative to production of TLR4 dependent cytokines/chemokines, resulting in a semioptimized lead (compound 1) that provided a starting point for further optimization studies. In this report, compounds belonging to three areas of structural modification were evaluated for biological activity using murine and human TLR4 reporter cells, primary murine bone marrow derived dendritic cells, and human peripheral blood mononuclear cells. The compounds bearing certain aryl groups at the C8 position, such as phenyl (36) and β-naphthyl (39), had potencies significantly greater than compound 1. Compound 36 displayed human TLR4 agonist activity at submicromolar concentrations. The computational analysis suggests that the improved potency of these C8-aryl derivatives may be the result of additional binding interactions at the interface of the TLR4/myeloid differentiation protein-2 (MD-2) complex.

3-(2-Carbamoylvinyl)-4,5-dimethylpyrrole-2-carboxylic acids as ligands at the NMDA glycine-binding site: A study on the 2-carbamoylvinyl chain modification

Twenty 4,5-dimethylpyrrole-2-carboxylic acids (5a-t) with different 2-carbamoylvinyl chains in position 3 were prepared to further investigate the relationships between structure and in vitro affinity for the strychnine-insensitive glycine-binding site. N