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Usage

Aromatic heterocyclic organic compound

1H-Pyrrole, 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)is a compound that contains a pyrrole ring, which is a five-membered aromatic ring with one or more atoms in the ring being different from carbon.

Methyl group at the 2-position

The compound has a methyl group (a carbon atom with three hydrogen atoms attached) attached to the 2-position of the pyrrole ring, which is the second carbon atom in the ring.

2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) substituent

The compound has a 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) group attached to the 5-position of the pyrrole ring, which is the fifth carbon atom in the ring.

Boron-containing heterocycle

The 1,3,2-dioxaborolane group is a boron-containing heterocycle, which is a ring structure containing atoms other than carbon, in this case, boron.

Versatile building block in organic synthesis

The 1,3,2-dioxaborolane group is commonly used in organic synthesis as a versatile building block for the preparation of various functionalized compounds.

Useful in the development of pharmaceuticals and agrochemicals

The presence of these groups in the chemical structure of 1H-Pyrrole, 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)makes it useful for various applications in the field of organic and medicinal chemistry, such as in the development of pharmaceuticals and agrochemicals.

Upstream product

• 636-41-9 2-methyl-1H-pyrrole 
• 73183-34-3 bis(pinacol)diborane 

Relevant academic research and scientific papers

Discovery of Reversible DNA Methyltransferase and Lysine Methyltransferase G9a Inhibitors with Antitumoral in Vivo Efficacy

Using knowledge- and structure-based approaches, we designed and synthesized reversible chemical probes that simultaneously inhibit the activity of two epigenetic targets, histone 3 lysine 9 methyltransferase (G9a) and DNA methyltransferases (DNMT), at nanomolar ranges. Enzymatic competition assays confirmed our design strategy: substrate competitive inhibitors. Next, an initial exploration around our hit 11 was pursued to identify an adequate tool compound for in vivo testing. In vitro treatment of different hematological neoplasia cell lines led to the identification of molecules with clear antiproliferative efficacies (GI50 values in the nanomolar range). On the basis of epigenetic functional cellular responses (levels of lysine 9 methylation and 5-methylcytosine), an acceptable therapeutic window (around 1 log unit) and a suitable pharmacokinetic profile, 12 was selected for in vivo proof-of-concept (Nat. Commun. 2017, 8, 15424). Herein, 12 achieved a significant in vivo efficacy: 70% overall tumor growth inhibition of a human acute myeloid leukemia (AML) xenograft in a mouse model.

Iridium-Catalyzed Direct Borylation of Five-Membered Heteroarenes by Bis(pinacolato)diboron: Regioselective, Stoichiometric, and Room Temperature Reactions

An iridium(I) complex generated from 1/ 2[Ir(OMe)(COD)]2 and 4,4′-di-tert-butyl-2,2′-bipyridine catalyzed the direct borylation of 2-substituted thiophenes, furans and pyrroles in stoichiometric amounts relative to bis(pinacolato)diboron in hex