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Usage

Uses

Used in Pharmaceutical Research and Development:
2,5-DIMETHYLPYRROLE-3-CARBOXYLIC ACID is used as a key intermediate in the synthesis of various pharmaceuticals for its potential applications in drug development. Its unique structure and functional group enable the creation of new therapeutic agents with diverse pharmacological properties.
Used in Agrochemicals:
In the agrochemical industry, 2,5-DIMETHYLPYRROLE-3-CARBOXYLIC ACID is used as a precursor for the synthesis of agrochemicals, such as pesticides and herbicides. Its incorporation into these products can enhance their effectiveness in controlling pests and weeds, contributing to improved crop yields and food security.
Used in Dyes and Pigments:
2,5-DIMETHYLPYRROLE-3-CARBOXYLIC ACID is utilized as a building block for the synthesis of dyes and pigments in the textile, paint, and ink industries. Its chemical properties allow for the development of vibrant and stable colorants that can be used in various applications, enhancing the aesthetic appeal and durability of products.
Used in Organic Synthesis:
As a versatile organic compound, 2,5-DIMETHYLPYRROLE-3-CARBOXYLIC ACID is used as a starting material or intermediate in the synthesis of complex organic molecules. Its carboxylic acid group facilitates various chemical reactions, enabling the formation of a wide range of organic compounds with diverse applications in research and industry.

InChI:InChI=1/C7H9NO2/c1-4-3-6(7(9)10)5(2)8-4/h3,8H,1-2H3,(H,9,10)/p-1

Upstream product

• 625-84-3 2,5-Dimethylpyrrole 
• 124-38-9 carbon dioxide 
• 67271-63-0 4-cyano-2,5-dimethyl-pyrrole-3-carboxylic acid ethyl ester 
• 2199-52-2 2,5-dimethyl-1H-pyrrole-3-carboxylic acid ethyl ester 

Downstream Products

• 69687-80-5 methyl 2,5-dimethyl-1H-pyrrole-3-carboxylate 
• 643744-39-2 2,5-dimethyl-1H-pyrrole-3-carboxylic acid (2-acetylphenyl)amide 

Relevant academic research and scientific papers

New iodo- and nitro-substituted pyrroles

Treating 2,5-dimethyl-4-ethoxycarbonyl- and 2,5-dimethyl-4-carboxypyrroles with iodine furnished 3-iodo-2,5-dimethyl-4-ethoxycarbonyl- and 3,4-diiodo-2,5-dimethylpyrroles. It was established that 3-iodo-2,5-dimethyl-4- ethoxycarbonylpyrrole reacted at heating with silver nitrite to afford 2,5-dimethyl-3-nitro-4-ethoxycarbonylpyrrole, and the same reagent oxidized 3,4-diiodo-2,5-dimethylpyrrole to give 3,4-diiodo-2-methyl-5-formylpyrrole. 2005 Pleiades Publishing, Inc.

Design, synthesis and biological activities of pyrrole-3-carboxamide derivatives as EZH2 (enhancer of zeste homologue 2) inhibitors and anticancer agents

Zeste enhancer homolog 2 (EZH2) is highly expressed in various malignant tumors, which could silence tumor suppressor genes via trimethylation of H3K27. Herein was first reported a novel series of pyrrole-3-carboxamide derivatives carrying a pyridone fragment as EZH2 inhibitors. By combining computational modeling, in vitro cellular assays and further rational structure-activity relationship exploration and optimization, compound DM-01 showed powerful inhibition towards EZH2. DM-01 was found to have significant ability to reduce the cellular H3K27me3 level in K562 cells in the Western blot test. Meanwhile, our data showed that knockdown EZH2 in A549 cells resulted in a decrease of cell sensitivity to DM-01 at 50 and 100 μM. DM-01 could also increase the transcription expression of DIRAS3 in a dose-dependent manner, a tumor suppressor in the downstream of EZH2, suggesting it was worth investigating further as a lead compound.

Pyrrole-3-formamide compound as well as preparation method and application thereof

The invention belongs to the technical field of medicines, and relates to a pyrrole-3-formamide compound as well as a preparation method and application thereof, in particular to a pyrrole-3-formamidecompound shown as a formula (I) or (II) and a pharmaceutically-acceptable salt thereof, wherein R to R and X are defined in the claims and description. The preparation of the compound mainly comprises performing Knorr pyrrole synthesis, Hantzsch pyrrole synthesis, decarboxylation, alkylation, hydrolysis, condensation, cyclization and reduction on ethyl acetoacetate or tert-butyl acetoacetate serving as the raw material. The pyrrole-3-formamide compound and the pharmaceutically-acceptable salt thereof have good treatment effects on tumors, and can be applied to the preparation of anti-tumor drugs. (The formulas (I) and (II) are shown in the description).

The pyrrolecarboxylic acid production

PROBLEM TO BE SOLVED: To provide a novel production method of pyrrole carboxylic acids, with which carbon dioxide can be utilized as a carbon source and a pyrrole carboxylic acid useful as a production raw material of medicines and agrochemicals is easily produced by making 1H-pyrrole react with carbon dioxide so that a carboxy group is directly introduced into a pyrrole skeleton in a low pressure of 1 MPa or less.SOLUTION: In introducing a carboxy group into a pyrrole skeleton by directly carboxylating 1H-pyrrole with carbon dioxide in a reaction solvent and in the presence of a catalyst, an excess of basic catalyst over 1H-pyrrole is used as the catalyst so that a pyrrole carboxylic acid is produced by introducing a carboxy group into a pyrrole skeleton in a low pressure of 1 MPa or less. The basic catalyst is lithium t-butoxide.

Synthesis and structure-activity relationships of a series of pyrrole cannabinoid receptor agonists

We designed and synthesized a series of pyrrole derivatives with the aim of investigating the structure-activity relationship (SAR) for the binding of non-classical agonists to CB1 and CB2 cannabinoid receptors. Superposition of two pyrrole-containing cannabinoid agonists, JWH-007 and JWH-161, allowed us to identify positions 1, 3 and 4 of the pyrrole nucleus as amenable to additional investigation. We prepared the 1-alkyl-2,5-dimethyl-3,4-substituted pyrroles 10a-e, 11a-d, 17, 21, 25 and the tetrahydroindole 15, and evaluated their ability to bind to and activate cannabinoid receptors. Noteworthy in this set of compounds are the 4-bromopyrrole 11a, which has an affinity for CB1 and CB2 receptors comparable to that of well-characterized heterocyclic cannabimimetics such as Win-55,212-2; the amide 25, which, although possessing a moderate affinity for cannabinoid receptors, demonstrates that the 3-naphthoyl group, commonly present in indole and pyrrole cannabimimetics, can be substituted by alternative moieties; and compounds 10d, 11d, showing CB1 partial agonist properties.