37013-86-8

Usage

Molecular class

Pyrrole derivatives

Functional groups

Carboxylic acid, ethyl ester, acetyl, ethyl, and methyl groups

Structure

A pyrrole ring with a carboxylic acid group at position 2, an ethyl ester group attached to the carboxylic acid, an acetyl group at position 4, an ethyl group at position 3, and a methyl group at position 5

Potential applications

Organic synthesis and medicinal chemistry

Need for further research

Yes, to fully understand its properties and potential uses.

Upstream product

• 123-54-6 acetylacetone 
• 4949-44-4 ethyl propanoylacetate 
• 75-36-5 acetyl chloride 

Downstream Products

• 16200-50-3 ethyl 3,4-diethyl-5-methylpyrrole-2-carboxylate 
• 34874-30-1 3,4-diethyl-2-methyl-1H-pyrrole 
• 2683-82-1 2,3,7,8,12,13,17,18-octaethyl-porphyrin 
• 16200-52-5 3,4-diethyl-1H-pyrrole 

Relevant academic research and scientific papers

Discovery of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as novel and potent bromodomain and extra-terminal (BET) inhibitors with anticancer efficacy

As epigenetic readers, bromodomain and extra-terminal domain (BET) family proteins bind to acetylated-lysine residues in histones and recruit protein complexes to promote transcription initiation and elongation. Inhibition of BET bromodomains by small molecule inhibitors has emerged as a promising therapeutic strategy for cancer. Herein, we describe our efforts toward the discovery of a novel series of 1-(5-(1H-benzo[d]imidazole-2-yl)-2,4-dimethyl-1H-pyrrol-3-yl)ethan-1-one derivatives as BET inhibitors. Intensive structural modifications led to the identification of compound 35f as the most active inhibitor of BET BRD4 with selectivity against BET family proteins. Further biological studies revealed that compound 35f can arrest the cell cycle in G0/G1 phase and induce apoptosis via decreasing the expression of c-Myc and other proteins related to cell cycle and apoptosis. More importantly, compound 35f showed favorable pharmacokinetic properties and antitumor efficacy in MV4-11 mouse xenograft model with acceptable tolerability. These results indicated that BET inhibitors could be potentially used to treat hematologic malignancies and some solid tumors.

2,3-Diazaporphyrins Bearing Two Nitrogen Atoms at the Periphery

The first synthesis of 2,3-diazaporphyrins 3 bearing two nitrogen atoms at peripheral positions from tripyrranes 1, prepared in situ by mild acidolysis and decarboxylation of the di-t-butyldicarboxylates, and 4H-1,2,4-triazol-3,5-dicarbaldehyde (2) is described, using the [3+1] principle of porphyrine cyclization. Similar to the parent porphyrins, the new diazaporphyrins 3 exhibit significantly shielded inner protons, reflecting the ring current of an 18 ? aromatic system and Soret bands in the UV-vis. spectra with extinctions comparable to those of octaethylporphyrin.