55817-72-6

Usage

Uses

Used in Pharmaceutical Research:
2-AMINO-1-BENZYL-4,5-DIMETHYL-1H-PYRROLE-3-CARBONITRILE is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its unique structure and potential for further modification, which aids in the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, 2-AMINO-1-BENZYL-4,5-DIMETHYL-1H-PYRROLE-3-CARBONITRILE serves as a valuable building block for creating complex organic molecules, leveraging its reactive functional groups and structural features.
Used in Anticancer Research:
2-AMINO-1-BENZYL-4,5-DIMETHYL-1H-PYRROLE-3-CARBONITRILE is utilized as a potential anticancer agent in research settings, where its biological activity is explored for its capacity to target and treat cancer cells.
Used as a Ligand in Drug Discovery:
In drug discovery, 2-AMINO-1-BENZYL-4,5-DIMETHYL-1H-PYRROLE-3-CARBONITRILE acts as a ligand for various receptors and enzymes, providing a means to study and modulate their activity, which is crucial for understanding disease mechanisms and developing targeted therapies.
Used in Medicinal Chemistry:
2-AMINO-1-BENZYL-4,5-DIMETHYL-1H-PYRROLE-3-CARBONITRILE is employed in medicinal chemistry as a tool to probe and optimize the interactions between drug candidates and their biological targets, thereby enhancing the potency and selectivity of new therapeutic agents.

InChI:InChI=1/C14H15N3/c1-10-11(2)17(14(16)13(10)8-15)9-12-6-4-3-5-7-12/h3-7H,9,16H2,1-2H3

Upstream product

• 109-77-3 malononitrile 
• 513-86-0 3-hydroxy-2-butanon 
• 100-46-9 benzylamine 
• 40513-26-6 3-benzylamino-butan-2-one 

Downstream Products

• 142311-32-8 1-benzyl-2-amino-3-cyano-5-oxo-7a-methyl-5,7a-dihydroindole 
• 144658-36-6 2-Amino-1-benzyl-3-cyano-7a-methyl-5-oxo-5,7a-dihydro-1H-indole-7-carboxylic acid methyl ester 
• 173458-77-0 7-benzyl-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol 
• 1179316-45-0 N'-(1-benzyl-3-cyano-4,5-dimethyl-1H-pyrrol-2-yl)-N,N-dimethylethanimidamide 
• 1309230-40-7 1-benzyl-2-(4-chlorophenyl)amino-4,5-dimethylpyrrole-3-carbonitrile 
• 1309230-42-9 1-benzyl-4,5-dimethyl-2-phenylaminopyrrole-3-carbonitrile 
• 1309230-33-8 methyl 4-(1-benzyl-3-cyano-4,5-dimethylpyrrol-2ylamino)benzoate 
• 1309230-29-2 2-(4-acetylphenyl)amino-1-benzyl-4,5-dimethylpyrrole-3-carbonitrile 
• 478033-10-2 N-(1-benzyl-3-cyano-4,5-dimethyl-1H-pyrrol-2-yl)-N-(methylsulfonyl)methanesulfonamide 
• 173458-86-1 (7-Benzyl-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(3,5-dichloro-phenyl)-amine 
• 1027236-75-4 (7-Benzyl-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-(3-chloro-phenyl)-methyl-amine 
• 173458-84-9 4-(m-Bromoanilino)-5,6-dimethyl-7-benzyl-pyrrolo[2,3-d]pyrimidine 
• 173458-83-8 4-(m-chloroanilino)-5,6-dimethyl-7-benzyl-pyrrolo[2,3-d]pyrimidine 
• 173458-85-0 4-(m-Fluoroanilino)-5,6-dimethyl-7-benzyl-pyrrolo[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Discovery and Optimization of Pyrrolopyrimidine Inhibitors of Interleukin-1 Receptor Associated Kinase 4 (IRAK4) for the Treatment of Mutant MYD88L265P Diffuse Large B-Cell Lymphoma

Herein we report the optimization of a series of pyrrolopyrimidine inhibitors of interleukin-1 receptor associated kinase 4 (IRAK4) using X-ray crystal structures and structure based design to identify and optimize our scaffold. Compound 28 demonstrated a favorable physicochemical and kinase selectivity profile and was identified as a promising in vivo tool with which to explore the role of IRAK4 inhibition in the treatment of mutant MYD88L265P diffuse large B-cell lymphoma (DLBCL). Compound 28 was shown to be capable of demonstrating inhibition of NF-κB activation and growth of the ABC subtype of DLBCL cell lines in vitro at high concentrations but showed greater effects in combination with a BTK inhibitor at lower concentrations. In vivo, the combination of compound 28 and ibrutinib led to tumor regression in an ABC-DLBCL mouse model.

Structure-activity relationship study and optimisation of 2-aminopyrrole-1-benzyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile as a broad spectrum metallo-β-lactamase inhibitor

A SAR study on derivatives of 2-amino-1-benzyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile 5a revealed that the 3-carbonitrile group, vicinal 4,5-diphenyl and N-benzyl side chains of the pyrrole are important for the inhibitory potencies of these compounds against members representing the three main subclasses of metallo-β-lactamases (MBLs), i.e. IMP-1 (representing the B1 subgroup), CphA (B2) and AIM-1 (B3). Coupling of 5a with a series of acyl chlorides and anhydrides led to the discovery of two N-acylamide derivatives, 10 and 11, as the two most potent IMP-1 inhibitors in this series. However, these compounds are less effective towards CphA and AIM-1. The N-benzoyl derivative of 5a retained potent in vitro activity against each of MBLs tested (with inhibition constants in the low μM range). Importantly, this compound also significantly enhanced the sensitivity of IMP-1, CphA- or AIM-1-producing cell cultures towards meropenem. This compound presents a promising starting point for the development of a universal MBL inhibitor, targeting members of each of the major subgroups of this family of enzymes.

PYRROLOPYRIMIDINES FOR PHARMACEUTICAL COMPOSITIONS

The present invention relates to novel pyrrolopyrimidine compounds and pharmaceutical compositions comprising said pyrrolopyrimidine compounds. Moreover, the present invention relates to the use of the pyrrolopyrimidine compounds of the invention for the