196106-96-4

Usage

Uses

Used in Pharmaceutical Research and Development:
4-BROMO-1H-PYRROLE-2-CARBOXAMIDE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block in the development of new drugs.
Used in Medicinal Chemistry:
4-BROMO-1H-PYRROLE-2-CARBOXAMIDE is employed as a lead compound in the discovery of new therapeutic agents. Its molecular properties are being investigated for their potential to modulate biological targets, contributing to the advancement of novel treatments for various diseases.
Used in Anti-Inflammatory Applications:
4-BROMO-1H-PYRROLE-2-CARBOXAMIDE is used as an anti-inflammatory agent for its potential to alleviate inflammation. 4-BROMO-1H-PYRROLE-2-CARBOXAMIDE's structure allows it to interact with specific biological pathways, offering a new avenue for the treatment of inflammatory conditions.
Used in Drug Discovery:
In the field of drug discovery, 4-BROMO-1H-PYRROLE-2-CARBOXAMIDE is used as a starting point for the design of new pharmaceuticals. Its chemical properties and potential biological activities are being explored to identify its efficacy and safety in treating a range of medical conditions.
Used in Therapeutic Agent Development:
4-BROMO-1H-PYRROLE-2-CARBOXAMIDE is utilized in the development of therapeutic agents targeting various diseases. Its potential as a treatment option is being assessed through preclinical and clinical studies to determine its effectiveness and suitability for human use.

Upstream product

• 4513-94-4 1H-pyrrole-2-carbonitrile 
• 4551-72-8 pyrrole-2-carboxamide 
• 72652-32-5 1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethanone 

Relevant academic research and scientific papers

Vanadate-dependent bromoperoxidases from Ascophyllum nodosum in the synthesis of brominated phenols and pyrroles

Bromoperoxidases from the brown alga Ascophyllum nodosum, abbreviated as VBrPO(AnI) and VBrPO(AnII), show 41% sequence homology and differ by a factor of two in the percentage of α-helical secondary structures. Protein monomers organize into homodimers for VBrPO(AnI) and hexamers for VBrPO(AnII). Bromoperoxidase II binds hydrogen peroxide and bromide by approximately one order of magnitude stronger than VBrPO(AnI). In oxidation catalysis, bromoperoxidases I and II turn over hydrogen peroxide and bromide similarly fast, yielding in morpholine-4-ethanesulfonic acid (MES)-buffered aqueous tert-butanol (pH 6.2) molecular bromine as reagent for electrophilic hydrocarbon bromination. Alternative compounds, such as tribromide and hypobromous acid are not sufficiently electrophilic for being directly involved in carbon-bromine bond formation. A decrease in electrophilicity from bromine via hypobromous acid to tribromide correlates in a frontier molecular orbital (FMO) analysis with larger energy gaps between the π-type HOMO of, for example, an alkene and the σ*Br,X-type LUMO of the bromination reagent. By using this approach, the reactivity of substrates and selectivity for carbon-bromine bond formation in reactions mediated by vanadate-dependent bromoperoxidases become predictable, as exemplified by the synthesis of bromopyrroles occurring naturally in marine sponges of the genera Agelas, Acanthella, and Axinella. The Royal Society of Chemistry.

Microwave-assisted fluorination of 2-acylpyrroles: Synthesis of fluorohymenidin

Treatment of mono- and nonbrominated 2-acylpyrroles with Selectfluor under microwave conditions leads to fluorination of the pyrrole ring in the 5-position. In particular, 2-trichloroacetylated pyrrole can be fluorinated. As an example, dihydrofluorohymenidin was synthesized and dehydrogenated to fluorohymenidin as the first fluorinated pyrrole-imidazole alkaloid. Introduction of the vinyl double bond was achieved by chlorination of the 2-aminoimidazole moiety, followed by dehydrochlorination at 100 °C in DMF.

Parameters for bromination of pyrroles in bromoperoxidase-catalyzed oxidations

Ester-, cyano-, and carboxamide-substituted 1H-pyrroles undergo electrophilic aromatic bromination, if treated with hydrogen peroxide and sodium bromide at pH 6.2 and 20 °C. Oxidation of bromide under such conditions is catalyzed by a vanadate(V)-dependent bromoperoxidase, in a substrate/enzyme ratio of 32-63 μmol %. To obtain maximum yields of bromopyrroles (up to 91%) by spending least amount of substrates and catalyst, hydrogen peroxide and sodium bromide have to be added continuously to the enzyme and the 2-acceptor-substituted pyrrole (1.5 mmol) in a solution of morpholine-4- ethanesulfonic acid buffer. This technique was applied to prepare two marine natural products under biomimetic conditions, that is, methyl 4,5-dibromopyrrole-2-carboxylate (from Agelas oroides) and 4,5-dibromopyrrole-2- carboxamide (from Acanthella carteri).