1192217-75-6

Basic information

• Product Name: 1-(benzenesulfonyl)-3-bromo-1H-pyrrole
• Synonyms: 1-(benzenesulfonyl)-3-bromo-1H-pyrrole
• CAS NO: 1192217-75-6
• Molecular Weight: 286.149
• Mol File: 1192217-75-6.mol

Chemical Properties

• CAS DataBase Reference: 1-(benzenesulfonyl)-3-bromo-1H-pyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(benzenesulfonyl)-3-bromo-1H-pyrrole(1192217-75-6)
• EPA Substance Registry System: 1-(benzenesulfonyl)-3-bromo-1H-pyrrole(1192217-75-6)

Safety Data

• Hazardous Substances Data: 1192217-75-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-(benzenesulfonyl)-3-bromo-1H-pyrrole is used as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure and reactivity allow for the creation of a wide range of chemical entities with potential applications across different industries.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-(benzenesulfonyl)-3-bromo-1H-pyrrole is utilized as a building block for the development of new pharmaceutical compounds. Its structural features can be leveraged to design molecules with specific biological activities, contributing to the discovery of novel therapeutic agents.
Used in Pharmaceutical Industry:
1-(benzenesulfonyl)-3-bromo-1H-pyrrole is used as a precursor in the synthesis of pharmaceutical compounds. Its presence in the molecular structure can influence the pharmacological properties of the final product, such as potency, selectivity, and bioavailability, making it a valuable component in drug design and development.
Used in Chemical Research:
1-(benzenesulfonyl)-3-bromo-1H-pyrrole is also used in chemical research to study the reactivity and properties of pyrrole-based systems. Understanding its behavior in various chemical reactions can provide insights into the development of new synthetic methods and the creation of innovative molecules with potential applications in various fields.

Upstream product

• 98-09-9 benzenesulfonyl chloride 
• 16851-82-4 N-phenylsulfonylpyrrole 

Downstream Products

• 1192217-76-7 methyl 3-bromo-1-(phenylsulfonyl)-1H-pyrrole-2-carboxylate 
• 1403942-38-0 methyl 1-(phenylsulfonyl)-3-(trifluoromethyl )-1H-pyrrole-2-carboxylate 
• 1229516-59-9 N,N-dimethyl-1-benzenesulfonyl-3-bromopyrrole-2-carboxamide 
• 1229516-60-2 N,N-dimethyl-1-benzenesulfonyl-4-bromopyrrole-2-carboxamide 
• 1229516-57-7 N-tert-butyl-1-benzenesulfonyl-3-bromopyrrole-2-carboxamide 
• 1229516-61-3 3-bromo-1-(phenylsulfonyl)-1H-pyrrole-2-carbaldehyde 
• 1229516-53-3 N-benzenesulfonyl-3-bromo-2-(phenylthio)pyrrole 
• 138371-99-0 N-benzenesulfonyl-4-bromopyrrole-2-carbaldehyde 
• 1229516-58-8 N-benzenesulfonyl-3-bromo-2-(4-methoxybenzoyl)pyrrole 
• 1229516-56-6 N-benzenesulfonyl-3-bromo-2-(α-hydroxy-4-methoxybenzyl)pyrrole 
• 1229516-62-4 N-benzenesulfonyl-4-bromo-2-(triisopropylsilyl)pyrrole 
• 1229516-63-5 N-benzenesulfonyl-3-bromo-2-(triisopropylsilyl)pyrrole 
• 1229516-52-2 N-benzenesulfonyl-3-bromo-2-(trimethylsilyl)pyrrole 
• 1229516-51-1 C₁₀H₇⁽²⁾HBrNO₂S 

Relevant articles and documents

Structural Basis of Metallo-β-lactamase Inhibition by N-Sulfamoylpyrrole-2-carboxylates

Metallo-β-lactamases (MBLs) can efficiently catalyze the hydrolysis of all classes of β-lactam antibiotics except monobactams. While serine-β-lactamase (SBL) inhibitors (e.g., clavulanic acid, avibactam) are established for clinical use, no such MBL inhibitors are available. We report on the synthesis and mechanism of inhibition of N-sulfamoylpyrrole-2-carboxylates (NSPCs) which are potent inhibitors of clinically relevant B1 subclass MBLs, including NDM-1. Crystallography reveals that the N-sulfamoyl NH2 group displaces the dizinc bridging hydroxide/water of the B1 MBLs. Comparison of crystal structures of an NSPC and taniborbactam (VRNX-5133), presently in Phase III clinical trials, shows similar binding modes for the NSPC and the cyclic boronate ring systems. The presence of an NSPC restores meropenem efficacy in clinically derived E. coli and K. pneumoniae blaNDM-1. The results support the potential of NSPCs and related compounds as efficient MBL inhibitors, though further optimization is required for their clinical development.

Rapid Access to Azabicyclo[3.3.1]nonanes by a Tandem Diverted Tsuji–Trost Process

A three-step synthesis of the 2-azabicyclo[3.3.1]nonane ring system from simple pyrroles, employing a combined photochemical/palladium-catalysed approach is reported. Substrate scope is broad, allowing the incorporation of a wide range of functionality relevant to medicinal chemistry. Mechanistic studies demonstrate that the process occurs by acid-assisted C?N bond cleavage followed by β-hydride elimination to form a reactive diene, demonstrating that efficient control of what might be considered off-cycle reactions can result in productive tandem catalytic processes. This represents a short and versatile route to the biologically important morphan scaffold.

Discovery of N-arylpyrroles as agonists of GPR120 for the treatment of type II diabetes

The discovery of a novel series of N-arylpyrroles as agonists of GPR120 (FFAR4) is discussed. One lead compound is a potent GPR120 agonist, has good selectivity for related receptor GPR40 (FFAR1), has acceptable PK properties, and is active in 2 models of Type 2 Diabetes in mice.

Unusually Facile Thermal Homodienyl-[1,5]-Hydrogen Shift Reactions in Photochemically Generated Vinyl Aziridines

A range of photochemically generated tri- and tetracyclic vinyl aziridines have been found to undergo a general and surprisingly low temperature ring opening through a [1,5]-hydrogen shift reaction. The rate of the process was found to be highly dependent on the structure and substitution around the azirdine ring and the alkene terminus, with some substrates being observed to undergo ring opening at temperatures as low as 25 °C. The rigid nature of these polycyclic systems precludes a conformational explanation of these rate differences, and an Eyring study confirmed a negligible entropic barrier to the reaction. However, the Eyring plots for two different aziridines systems showed a significant difference in their enthalpies of activation. It is therefore believed that the levels of aziridine ring strain, as well as electronic effects, are the dominant factors in this sequence.

Design and synthesis of lamellarin D analogues targeting topoisomerase I

(Chemical Equation Presented) A general synthetic route to rationally designed lamellarinDanalogues, 1-dearyllamellarinD(1) and 1-substituted 1-dearyllamellarin D (2), has been developed. The key pentacyclic intermediate 22 was prepared by palladium-catalyzed direct arylation of 12, which in turn was synthesized via C-2-selective lithiation of 15 followed by palladium-catalyzed cross-coupling as the key reactions. Compound 22 was converted to a wide range of C-1-substituted analogues 2 via regioselective electrophilic substitution and palladium-catalyzed cross-coupling reactions.