50371-51-2

Usage

Uses

Used in Organic Synthesis:
2,2,2-TRICHLORO-1-(4,5-DICHLORO-1H-PYRROL-2-YL)ETHANONE is used as a reagent in organic synthesis for its ability to introduce the 2,2,2-trichloroethyl group to various substrates, facilitating the formation of new chemical compounds and structures.
Used in Pesticide Industry:
In the pesticide industry, 2,2,2-TRICHLORO-1-(4,5-DICHLORO-1H-PYRROL-2-YL)ETHANONE is used as an active ingredient to control and eliminate pests due to its toxic effects on living organisms. However, its use must be carefully managed to minimize potential hazards to the environment and human health.

InChI:InChI=1/C6H2Cl5NO/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

• 50371-72-7 4,5-dichloro-pyrrole-2-carboxylic acid benzylamide 
• 50371-74-9 2',3',4,5-tetrachloropyrrole-2-carboxanilide 
• 50371-49-8 3',4,4',5-tetrachloropyrrole-2-carboxanilide 
• 50371-73-8 2',4,5-trichloropyrrole-2-carboxanilide 
• 50371-47-6 4,4',5-trichloropyrrole-2-carboxanilide 
• 50371-46-5 3',4,5-trichloropyrrole-2-carboxanilide 
• 50372-71-9 (4,5-dichloro-pyrrol-2-yl)-(2,5-dimethoxy-phenyl)-methanone 
• 50372-73-1 (4,5-dichloro-pyrrol-2-yl)-(2,4-dimethoxy-phenyl)-methanone 
• 50372-74-2 (4,5-dichloro-pyrrol-2-yl)-(3,4-dimethoxy-phenyl)-methanone 
• 50372-59-3 (4,5-dichloro-pyrrol-2-yl)-(2,4-dihydroxy-phenyl)-methanone 
• 1197-12-2 4,5-Dichlor-1H-pyrrol-2-carbonsaeure-methylester 
• 1010732-15-6 2-[(3-(3-bromo-4,5-dichloro-2-[(2-hydroxyphenyl)carbonyl]-1H-pyrrol-1-yl)-4,5-dichloro-1H-pyrrol-2-yl)carbonyl]phenol 
• 1416956-61-0 3-bromo-4,5-dichloro-1-(4,5-dichloro-2-[(2-methoxyphenyl)carbonyl]-1H-pyrrol-3-yl)-2-[(2-methoxyphenyl)carbonyl]-1H-pyrrole 
• 1416956-65-4 C₃₁H₂₃BrCl₂N₂O₆S 

Relevant academic research and scientific papers

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.

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.

NOVEL COMPOUNDS USEFUL FOR THE TREATMENT OF BACTERIAL INFECTIOUS DISEASES

Compounds are disclosed that have a formula represented by the following: wherein A, B, R1, R2 and R3 are as defined herein. Novel compounds of the invention may be prepared as a pharmaceutical composition, and may be useful in the treatment of infectious diseases, in particular bacterial infectious diseases. The compounds may be active against a specific enzyme in the bacterial DNA replicative process, DNA polymerase IIIE.

N-Chloro-N-methoxybenzenesulfonamide: A Chlorinating Reagent

A structurally simple and reactive chlorinating reagent, N-chloro-N-methoxybenzenesulfonamide, was conveniently and economically prepared in high yield. 1,3-Diketones, β-keto esters, benzoyl trifluoroacetones, phenols, anisoles, heteroarenes, and aromatic amines were successfully chlorinated, and the products were obtained in good to high yields.

BRANIMYCIN DERIVATIVES AND THEIR USE FOR THE TREATMENT OF BACTERIAL INFECTIOUS DISEASES

Compounds are disclosed that have a formula represented by Formula (I) wherein A, B, R1, R2 and R3 are as defined herein. Novel compounds of the invention may be prepared as a pharmaceutical composition, and may be useful in the treatment of infectious diseases, in particular bacterial infectious diseases. The compounds may be active against a specific enzyme in the bacterial DNA replicative process, DNA polymerase IIIE.

CFBSA: a novel and practical chlorinating reagent

A structurally simple, highly reactive chlorinating reagent, N-chloro-N-fluorobenzenesulfonylamine (CFBSA), was conveniently prepared from inexpensive Chloramine B in high yield. A wide range of substrates were chlorinated with it to obtain products in good to high yields and appropriate selectivity.

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.

Racemic marinopyrrole B by total synthesis

The first synthesis of marinopyrrole B, which is highly active against methicillin-resistant Staphylococcus aureus, is described. The route involved constructing a pyrrole ring on the nitrogen of a 3-bromo-4,5-dichloropyrrole by N-alkylation with a special Michael acceptor having an allylic leaving group; the second pyrrole ring was then formed by a Paal-Knorr reaction.

An efficient approach to dispacamide A and its derivatives

Dispacamide A and new analogs of this marine alkaloid were prepared in seven steps with an overall yield ranging from 12 to 33%. The key step of the strategy was a stereocontrolled Knoevenagel condensation under microwave dielectric heating in the last step. In this condensation, the 2-aminoimidazolin-4-one hydrochloride partners 10a-c were synthesized in three steps with good overall yields (33-79%) via the ring closure of N-guanidino acetic acids 9a-c and the aldehydes 5a,b as the two others building-blocks, in 3 steps with 60-66% overall yields. The six synthetic products have been obtained with a Z geometry about their exocyclic bond on the basis of 13C/1H long-range coupling constants using a gHSQMBC experiment.