35302-72-8

Usage

Uses

Used in Pharmaceutical Industry:
2-(Trichloroacetyl)pyrrole is used as a building block for the synthesis of complex pharmaceutical compounds, such as Oroidin, Hymenidin, and Clathrodin. Its unique chemical properties and reactivity make it a valuable component in the development of novel drugs with potential therapeutic applications.
In the synthesis of Oroidin, 2-(Trichloroacetyl)pyrrole contributes to the formation of a potent antifungal agent, which is particularly effective against a wide range of fungal infections. Its role in the development of Hymenidin and Clathrodin highlights its versatility in creating diverse pharmaceutical compounds with potential applications in various therapeutic areas.
Overall, 2-(Trichloroacetyl)pyrrole plays a crucial role in the pharmaceutical industry as a versatile building block for the creation of complex and potentially effective pharmaceutical compounds. Its ability to undergo acylation and participate in the synthesis of various drugs underscores its importance in drug development and innovation.

InChI:InChI=1/C6H4Cl3NO/c7-6(8,9)5(11)4-2-1-3-10-4/h1-3,10H

Upstream product

• 109-97-7 pyrrole 
• 918-00-3 1,1,1-trichloroacetone 
• 4124-31-6 trichloroacetic acid anhydride 
• 96-54-8 N-Methylpyrrole 
• 76-02-8 trifluoroacetyl chloride 
• 7440-44-0 pyrographite 

Downstream Products

• 80242-22-4 2-acetylpyrrole-4-carbonitrile 
• 80242-23-5 trichloroacetyl-(4-cyano-1H-pyrrol-2-yl) 
• 111468-90-7 1-(5-(2,2,2-trichloroacetyl)-1H-pyrrol-3-yl)propan-1-one 
• 72652-34-7 1-(4-acetyl-1H-pyrrol-2-yl)-2,2,2-trichloroethan-1-one 
• 111468-91-8 4-butyryl-2-(trichloroacetyl)pyrrole 
• 132911-42-3 N-Methyl-1H-pyrrole-2-carboxamide 
• 72652-32-5 1-(4-bromo-1H-pyrrol-2-yl)-2,2,2-trichloroethanone 
• 50371-52-3 4,5-dibromopyrrol-2-yl trichloromethyl ketone 
• 174417-17-5 4-(4-methoxybenzoyl)-2-trichloroacetylpyrrole 
• 5427-82-7 1H-pyrrole-2-carbonyl chloride 
• 1193-62-0 methyl Pyrrole-2-carboxylate 
• 53391-50-7 2,2,2-trichloro-1-(4-nitro-1H-pyrrol-2-yl)ethan-1-one 
• 311807-80-4 1-[(5-chloro-2-nitrophenyl)sulfonyl]-2-trichloroacetyl-1H-pyrrole 
• 504434-16-6 1H-pyrrole-2-carboxylic acid methylprop-2-ynylamide 

Relevant academic research and scientific papers

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.

Bioactive Bromopyrrole Metabolites from the Caribbean Sponge Agelas conifera

Biologically active extracts of the Carribean sponge Agelas conifera have yielded, in exhaustive studies, the diacetate salts of seven new bromopyrroles (1, 3-8), as well as that of the known debromooroidin dimer sceptrin (2).These compounds were found to be antiviral and antibacterial and were active in barnacle settlement and biochemical prophage induction assays.The structures assigned were based on spectroscopic comparison to sceptrin and two-dimensional NMR data.Synthetic bromopyrroles were used to verify bromine substitution patterns.The oxysceptrins (4, 5) are characterized by their aminoimidazolinone group, the ageliferins (6-8) by a unique cyclohexene-based skeleton.

Isolation and synthesis of 4-bromopyrrole-2-carboxyarginine and 4-bromopyrrole-2-carboxy-N(ε)-lysine from the marine sponge Stylissa caribica

Two new bromopyrrole alkaloids were isolated from the Caribbean sponge Stylissa caribica. The new natural products, 4-bromopyrrole-2-carboxyarginine (1) and 4-bromopyrrole-2-carboxy-N(ε)-lysine (2), are derivatives of amino acids linked with a 4-bromopyrrole-2-carboxylic acid. The structures were elucidated on the basis of NMR and MS/MS data and their absolute configurations assigned via synthesis.

Synthetic method 3 - ethylamine-based pyrrole compound (by machine translation)

The invention discloses a synthesis method of 3 - ethylamine-based pyrrole compounds, which is as follows: pyrrole is reacted with trichloroacetyl chloride to generate o-trichloroacetyl pyrrole and then treated with sodium alkoxide to obtain ortho-pyrrole formate, ortho-pyrrole formate and substituted nitrostyrene in anhydrous AlCl. 3 Under catalysis, compound 3 is obtained, and compound 3 is directly reduced without purification to give the target product 3 -ethylamine yrrolopyrrole. To the method, a single 3 -ethylamine-based pyrrole compound can be obtained in high yield by introducing ester groups into the pyrrole N ortho-position, 2 -ethylamine yrrolopyrrole is avoided, and the problem that the selectivity is not good when a Fourier reaction is carried out with pyrrole as a raw material is solved. The yield of a series of substituted nitrostyrene is above 75%, and the substrate range is wide. (by machine translation)

Computer Modeling and Synthesis of Potential Inhibitors of Tyrosine Kinase BCR-ABL with the T315I Mutation

Abstract—: A comparative analysis of the interaction of the chimeric protein BCR-ABL, of the normal type and with the T315I mutation, with known inhibitors as well as compounds potentially capable of inhibiting the mutant protein has been carried out by computer modeling. It has been shown that the compounds proposed are incorported into the structure of the protein with the retention of the basic hydrogen bonds and intermolecular interactions. Two structures containing the pyrrole cycle have been synthesized, which, according to the results of computer modeling, appear to be most promising.

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.

Further Developments of the Phenyl-Pyrrolyl Pentane Series of Nonsteroidal Vitamin D Receptor Modulators as Anticancer Agents

The vitamin D3 receptor (VDR), which belongs to the nuclear-receptor superfamily, is a potential molecular target for anticancer-drug discovery. In this study, a series of nonsteroidal vitamin D mimics with phenyl-pyrrolyl pentane skeletons wit

Substrate Controlled Regioselective Bromination of Acylated Pyrroles Using Tetrabutylammonium Tribromide (TBABr3)

Electrophilic bromination of pyrroles bearing carbonyl substituents at C-2 typically results in a mixture of the 4- and 5-brominated species, generally favoring the 4-position. Herein, we describe a substrate-controlled regioselective bromination in which

RESORCINOL DERIVATIVE AS HSP90 INHIBITOR

The present invention relates to a compound represented by formula (I) of a resorcinol derivative as an HSP90 inhibitor or pharmaceutically accepted salts thereof. The compound in the present invention has the activity of inhibiting heat shock protein HSP90. Therefore, the compound in the present invention is used to treat proliferative diseases such as cancer and neurodegenerative diseases. The present invention further provides the compounds and preparation methods for pharmaceutical compositions comprising the compounds, a method for treating diseases, and pharmaceutical compositions comprising the compounds.

Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties

Intramolecular nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole esters is described. Efficient routes towards the synthesis of pyrrolopyrazinone, pyrrolotriazinone and pyrrolooxazinone have been developed. First, N-alkyne-substituted pyrrole ester derivatives were synthesized. Introduction of various substituents into the alkyne functionality was accomplished by a copper-catalyzed cross-coupling reaction. Nucleophilic cyclization of N-alkyne-substituted methyl 1H-pyrrole-2-carboxylates with hydrazine afforded the 6-exo-dig/6-endo-dig cyclization products depending on the electronic nature of the substituents attached to the alkyne. On the other hand, cyclization of N-alkyne-substituted methyl 1H-pyrrole-2-carboxylates with iodine only resulted in the formation of the 6-endo-dig cyclization product regardless of the substitution of the alkyne functionality.