50371-52-3

Usage

Uses

Used in Personal Care Products:
2,2,2-TRICHLORO-1-(4,5-DIBROMO-1H-PYRROL-2-YL)-1-ETHANONE is used as an antibacterial and antifungal agent in personal care products such as soaps, toothpaste, and body wash. Its ability to inhibit the growth of bacteria and fungi helps maintain hygiene and prevent infections.
Used in Textiles:
In the textile industry, 2,2,2-TRICHLORO-1-(4,5-DIBROMO-1H-PYRROL-2-YL)-1-ETHANONE is used as an additive to impart antibacterial and antifungal properties to fabrics. This helps in reducing odor, maintaining cleanliness, and extending the life of the textiles.
Used in Plastics and Kitchenware:
2,2,2-TRICHLORO-1-(4,5-DIBROMO-1H-PYRROL-2-YL)-1-ETHANONE is used in the production of plastics and kitchenware to provide antibacterial and antifungal properties. This helps in preventing the growth of harmful microorganisms, ensuring cleanliness, and maintaining the longevity of the products.
Environmental and Health Concerns:
Despite its widespread use, 2,2,2-TRICHLORO-1-(4,5-DIBROMO-1H-PYRROL-2-YL)-1-ETHANONE has been found to persist in the environment, accumulating in water and soil. It has also been detected in human tissues and breast milk, raising concerns about its potential harmful effects on human health and the ecosystem. As a result, some countries have imposed restrictions and bans on its use in certain products to mitigate these risks.

InChI:InChI=1/C6H2Br2Cl3NO/c7-2-1-3(12-5(2)8)4(13)6(9,10)11/h1,12H

Upstream product

• 35302-72-8 pyrrol-2-yl trichloromethyl ketone 

Downstream Products

• 34649-22-4 oroidin 
• 848899-39-8 4,5-dibromo-1H-pyrrole-2-carboxylic acid [3-(2-phenylsulfanyl-3H-imidazol-4-yl)propyl]amide 
• 1242516-96-6 C₁₇H₁₄Br₂Cl₃NO₄ 
• 1242516-98-8 C₂₃H₂₅Br₂Cl₃N₂O₆ 
• 1242516-95-5 C₁₇H₁₆Br₂Cl₃NO₃ 
• 1408118-24-0 2-(4,5-dibromo-1H-pyrrol-2-yl)-5-styryl-1,3,4-oxadiazole 
• 1408118-26-2 C₁₂H₇Br₂N₃O₂ 
• 1408118-29-5 C₁₂H₅Br₂ClFN₃O 
• 1408118-30-8 C₁₂H₆Br₂N₄O₃ 
• 1408118-32-0 C₁₂H₇Br₂N₃O 
• 1408118-42-2 C₁₂H₇Br₂N₃OS 
• 1408118-15-9 C₁₃H₉Br₂N₃O 
• 1408118-18-2 C₁₂H₈Br₂N₄O 
• 1408118-20-6 C₁₂H₆Br₂ClN₃O 

Relevant academic research and scientific papers

A convenient synthesis of pseudoceratidine and three analogs for biological evaluation

The recently isolated marine natural product pseudoceratidine (1) has been synthesized from 2-trichloronactylpyrrole. Bromination in the 4- and 5-position followed by nucleophilic displacement of the trichloromethyl group with spermidine gave 1 in 79% yield. The procedure is general and can easily be adopted to the preparation of other derivatives. This was demonstrated by the synthesis of a 5,5'-didebromo derivative (2) and two analogs (3-4). The compounds 1-4 have been tested for antibacterial activity and the results compared to a previous study. Also activity against die marine brine shrimp Artemia salina is reported.

Latonduines A and B, new alkaloids isolated from the marine sponge Stylissa carteri: Structure elucidation, synthesis, and biogenetic implications

(Matrix Presented) Latonduines A (6) and B (7), two new alkaloids with unprecedented heterocyclic skeletons, have been isolated from the Indonesian marine sponge Stylissa carteri. The structures of the latonduines were elucidated by analysis of spectroscopic data and confirmed by the total synthesis of latonduine A (6). It is proposed that ornithine is the biogenetic precursor to the aminopyrimidine fragment of the latonduines.

From Synthetic Simplified Marine Metabolite Analogues to New Selective Allosteric Inhibitor of Aurora B Kinase

Significant inhibition of Aurora B was achieved by the synthesis of simplified fragments of benzosceptrins and oroidin belonging to the marine pyrrole-2-aminoimidazoles metabolites isolated from sponges. Evaluation of kinase inhibition enabled the discovery of a synthetically accessible rigid acetylenic structural analogue EL-228 (1), whose structure could be optimized into the potent CJ2-150 (37). Here we present the synthesis of new inhibitors of Aurora B kinase, which is an important target for cancer therapy through mitosis regulation. The biologically oriented synthesis yielded several nanomolar inhibitors. The optimized compound CJ2-150 (37) showed a non-ATP competitive allosteric mode of action in a mixed-type inhibition for Aurora B kinase. Molecular docking identified a probable binding mode in the allosteric site "F"and highlighted the key interactions with the protein. We describe the improvement of the inhibitory potency and specificity of the novel scaffold as well as the characterization of the mechanism of action.

Synthesis and antibacterial analysis of analogues of the marine alkaloid pseudoceratidine

In an effort to gain more understanding on the structure activity relationship of pseudoceratidine 1, a di-bromo pyrrole spermidine alkaloid derived from the marine sponge Pseudoceratina purpurea that has been shown to exhibit potent biofouling, anti-fungal, antibacterial, and anti-malarial activities, a large series of 65 compounds that incorporated several aspects of structural variation has been synthesised through an efficient, divergent method that allowed for a number of analogues to be generated from common precursors. Subsequently, all analogues were assessed for their antibacterial activity against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. Overall, several compounds exhibited comparable or better activity than that of pseudoceratidine 1, and it was found that this class of compounds is generally more effective against Gram-positive than Gram-negative bacteria. Furthermore, altering several structural features allowed for the establishment of a comprehensive structure activity relationship (SAR), where it was concluded that several structural features are critical for potent anti-bacterial activity, including di-halogenation (preferable bromine, but chlorine is also effective) on the pyrrole ring, two pyrrolic units in the structure and with one or more secondary amines in the chain adjoining these units, with longer chains giving rise to better activities.

Synthesis of 4,4-dimethyl-2-(2-pyrrolyl)-2-oxazolines

– A practical synthesis of 4,4-dimethyl-2-oxazolines on pyrrole was achieved via the cyclization of the corresponding amides, which were derived from the trichloroacetylpyrroles. The established conditions were applicable to pyrroles bearing a ketone or an ester moiety. In addition to pyrroles, the method could be extended to the synthesis of the indole derivative.

Tryptamine derivatives disarm colistin resistance in polymyxin-resistant gram-negative bacteria

The last three decades have seen a dwindling number of novel antibiotic classes approved for clinical use and a concurrent increase in levels of antibiotic resistance, necessitating alternative methods to combat the rise of multi-drug resistant bacteria. A promising strategy employs antibiotic adjuvants, non-toxic molecules that disarm antibiotic resistance. When co-dosed with antibiotics, these compounds restore antibiotic efficacy in drug-resistant strains. Herein we identify derivatives of tryptamine, a ubiquitous biochemical scaffold containing an indole ring system, capable of disarming colistin resistance in the Gram-negative bacterial pathogens Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli while having no inherent bacterial toxicity. Resistance was overcome in strains carrying endogenous chromosomally-encoded colistin resistance machinery, as well as resistance conferred by the mobile colistin resistance-1 (mcr-1) plasmid-borne gene. These compounds restore a colistin minimum inhibitory concentration (MIC) below the Clinical & Laboratory Sciences Institute (CLSI) breakpoint in all resistant strains.

Synthesis and Absolute Stereochemical Reassignment of Mukanadin F: A Study of Isomerization of Bromopyrrole Alkaloids with Implications on Marine Natural Product Isolation

Synthesis of both enantiomers of mukanadin F was achieved by using a seven step synthesis. Comparison of the optical rotation data of synthetic samples to that reported for the isolated natural product determined that the absolute configuration of the natural product is 9S and not the reported 9R. Further studies established that the reported low magnitude of optical rotation in the isolated sample is due to compounds of this type undergoing isomerization and racemization under benign laboratory conditions. Additionally the synthetic methods developed were applied to synthesize mukanadins B and D.

Isolation, Derivative Synthesis, and Structure-Activity Relationships of Antiparasitic Bromopyrrole Alkaloids from the Marine Sponge Tedania brasiliensis

The isolation and identification of a series of new pseudoceratidine (1) derivatives from the sponge Tedania brasiliensis enabled the evaluation of their antiparasitic activity against Plasmodium falciparum, Leishmania (Leishmania) amazonensis, Leishmania (Leishmania) infantum, and Trypanosoma cruzi, the causative agents of malaria, cutaneous leishmaniasis, visceral leishmaniasis, and Chagas disease, respectively. The new 3-debromopseudoceratidine (4), 20-debromopseudoceratidine (5), 4-bromopseudoceratidine (6), 19-bromopseudoceratidine (7), and 4,19-dibromopseudoceratidine (8) are reported. New tedamides A-D (9-12), with an unprecedented 4-bromo-4-methoxy-5-oxo-4,5-dihydro-1H-pyrrole-2-carboxamide moiety, are also described. Compounds 4 and 5, 6 and 7, 9 and 10, and 11 and 12 have been isolated as pairs of inseparable structural isomers differing in their sites of bromination or oxidation. Tedamides 9+10 and 11+12 were obtained as optically active pairs, indicating an enzymatic formation rather than an artifactual origin. N12-Acetylpseudoceratidine (2) and N12-formylpseudoceratidine (3) were obtained by derivatization of pseudoceratidine (1). The antiparasitic activity of pseudoceratidine (1) led us to synthesize 23 derivatives (16, 17, 20, 21, 23, 25, 27-29, 31, 33, 35, 38, 39, 42, 43, 46, 47, 50, and 51) with variations in the polyamine chain and aromatic moiety in sufficient amounts for biological evaluation in antiparasitic assays. The measured antimalarial activity of pseudoceratidine (1) and derivatives 4, 5, 16, 23, 25, 31, and 50 provided an initial SAR evaluation of these compounds as potential leads for antiparasitics against Leishmania amastigotes and against P. falciparum. The results obtained indicate that pseudoceratidine represents a promising scaffold for the development of new antimalarial drugs.

Synthesis and biological evaluation of pyrrole-2-carboxamide derivatives: Oroidin analogues

The reaction of pyrrole or dibromopyrrole-2-trichloroacetone with various amines results in the series of novel pyrrole-2-carboxamide bearing aromatic heterocycle or aryl or alkyl groups. Synthesized molecules were evaluated for their in vitro antibacterial activities. Most of the compounds exhibited potent activity against both Gram-positive and negative pathogens.

Reduction of 2,2,2-trichloro-1-arylethanones by RMgX: Mechanistic investigation and the synthesis of substituted α,α-dichloroketones

2,2,2-Trichloro-1-arylethanones undergo high yielding reductions to the corresponding 2,2-dichloro-1-arylethanones in the presence of RMgX. A single electron transfer mechanism for the reaction is proposed based on trapping experiments. Reaction of the intermediate enolates with a range of electrophiles is described, providing a convenient route to substituted α,α- dichloro-β-hydroxyketones and related molecules. The Royal Society of Chemistry 2013.