28494-49-7

Usage

Derived from

Pyrrole (a five-membered aromatic heterocyclic compound)

Groups present

Carbonyl chloride group, nitro group

Suitable for

Various chemical reactions and organic syntheses

Used in

Production of pharmaceuticals and agrochemicals

Known for

Strong electrophilic nature and reactivity towards nucleophiles

Value in organic chemistry

Valuable building block

Precautions

Handle with caution due to potential hazards and reactivity.

Upstream product

• 5930-93-8 4-nitropyrrole-2-carboxylic acid 
• 5930-92-7 Ethyl 4-nitropyrrole-2-carboxylate 

Downstream Products

• 402912-86-1 4-{3,5-dimethyl-4-[(4-nitro-1H-pyrrole-2-carbonyl)-amino]-phenyl}-4-(3,5-dimethyl-4-pentafluorobenzoylamino-phenyl)-piperidine-1-carboxylic acid benzyl ester 
• 402912-81-6 (1-benzyloxycarbonyl)-N-(4-nitropyrrole-2-carboxy)[4,4-bis(4-amino-3,5-dimethylphenyl)]piperidine 
• 402912-79-2 4-{4-[(anthracene-9-carbonyl)-amino]-3,5-dimethyl-phenyl}-4-{3,5-dimethyl-4-[(4-nitro-1H-pyrrole-2-carbonyl)-amino]-phenyl}-piperidine-1-carboxylic acid benzyl ester 
• 936027-39-3 4-[4-(2,6-dimethyl-benzoylamino)-3,5-dimethyl-phenyl]-4-{3,5-dimethyl-4-[(4-nitro-1H-pyrrole-2-carbonyl)-amino]-phenyl}-piperidine-1-carboxylic acid benzyl ester 
• 936027-40-6 4-{4-[(acridine-9-carbonyl)-amino]-3,5-dimethyl-phenyl}-4-{3,5-dimethyl-4-[(4-nitro-1H-pyrrole-2-carbonyl)-amino]-phenyl}-piperidine-1-carboxylic acid benzyl ester 
• 936027-41-7 4-[4-(2,6-dimethyl-4-nitro-benzoylamino)-3,5-dimethyl-phenyl]-4-{3,5-dimethyl-4-[(4-nitro-1H-pyrrole-2-carbonyl)-amino]-phenyl}-piperidine-1-carboxylic acid benzyl ester 
• 113598-28-0 (4S)-(+)-Anthelvencin A 
• 113598-34-8 (4R)-(-)-anthelvencin A 
• 851590-22-2 N-{4-[N-benzyl-N-(t-butoxycarbonyl)amino]-1-methylpyrrole-2-carbonyl}pyrrolidine 
• 851590-15-3 N-[4-(2-nitrophenylamino)-1-methylpyrrole-2-carbonyl]pyrrolidine 
• 851590-03-9 [1-methyl-4-(4-nitro-phenylamino)-1H-pyrrol-2-yl]-pyrrolidin-1-yl-methanone 
• 851590-19-7 [4-(3,5-dimethyl-phenylamino)-1-methyl-1H-pyrrol-2-yl]-pyrrolidin-1-yl-methanone 

Relevant academic research and scientific papers

Substituent effects on aromatic stacking interactions

Synthetic supramolecular zipper complexes have been used to quantify substituent effects on the free energies of aromatic stacking interactions. The conformational properties of the complexes have been characterised using NMR spectroscopy in CDCl3, and by comparison with the solid state structures of model compounds. The structural similarity of the complexes makes it possible to apply the double mutant cycle method to evaluate the magnitudes of 24 different aromatic stacking interactions. The major trends in the interaction energy can be rationalised using a simple model based on electrostatic interactions between the π-faces of the two aromatic rings. However, electrostatic interactions between the substituents of one ring and the π-face of the other make an additional contribution, due to the slight offset in the stacking geometry. This property makes aromatic stacking interactions particularly sensitive to changes in orientation as well as the nature and location of substituents. This journal is The Royal Society of Chemistry.

Novel non-steroidal/non-anilide type androgen antagonists: Discovery of 4-substituted pyrrole-2-carboxamides as a new scaffold for androgen receptor ligands

We designed and synthesized novel pyrrole-2-carboxamide derivatives as androgen antagonists. Compounds 10 and 13 bearing benzylamine or aniline at the 4-position of the pyrrole ring showed moderate androgen antagonistic activity, and inhibited the androgen-dependent growth of Shionogi carcinoma cells (SC-3). Study of the structure-activity relationships of compound 13 led to a potent androgen antagonist 36, which has higher affinity than flutamide (4) for androgen nuclear receptor (AR). Thus, pyrrole-2-carboxamide is a new scaffold for developing AR antagonists.