1199-64-0

Usage

Ester derivative

pyrrole-2,5-dicarboxylic acid The compound is derived from pyrrole-2,5-dicarboxylic acid by replacing one of the carboxylic acid groups with a methyl ester group.

Common use

organic synthesis and pharmaceutical research The compound is frequently used in the synthesis of new organic compounds and as a building block in the development of pharmaceuticals.

Applications

production of pharmaceuticals, dyes, and agricultural chemicals The compound is utilized in the manufacturing of various products, including medications, coloring agents, and chemicals for agricultural purposes.

Intermediate in manufacturing

fine chemicals and specialty materials 1H-pyrrole-2,5-dicarboxylic acid monomethyl ester serves as a precursor in the production of other chemical compounds and materials with specific properties.

Potential biological activity

therapeutic uses in treatment of diseases The compound is being investigated for its possible effects on biological systems, with the aim of discovering its potential applications in treating various diseases.

Versatile compound

important in chemistry and medicine 1H-pyrrole-2,5-dicarboxylic acid monomethyl ester has a wide range of applications and is significant in both the fields of chemistry and medicine due to its unique properties and potential uses.

Upstream product

• 35302-72-8 pyrrol-2-yl trichloromethyl ketone 
• 1193-62-0 methyl Pyrrole-2-carboxylate 
• 74-88-4 methyl iodide 
• 1197-13-3 methyl 5-formyl-1H-pyrrole-2-carboxylate 

Downstream Products

• 1408284-18-3 3,5-bis((5-(butylcarbamoyl)-1H-pyrrole-2-carboxamido)methyl)phenyl 5-(dimethylamino)naphthalene-1-sulfonate 
• 1408284-24-1 N₂,N₂'-(5-(tert-butyldimethylsilyloxy)-1,3-phenylene) bis(methylene)bis(N₅-butyl-1H-pyrrole-2,5-dicarboxamide) 
• 852200-64-7 1H-pyrrole-2,5-dicarboxylic acid bis-phenylamide 
• 347362-31-6 5-chlorocarbonyl-1H-pyrrole-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

The role of N-terminal heterocycles in hydrogen bonding to α-chymotrypsin

A series of dipeptide aldehydes containing different N-terminal heterocycles was prepared and assayed in vitro against α-chymotrypsin to ascertain the importance of the heterocycle in maintaining a β-strand geometry while also providing a hydrogen bond do

Lynamicin D an antimicrobial natural product affects splicing by inducing the expression of SR protein kinase 1

The first total synthesis of the antimicrobial natural product lynamicin D has been developed using a Suzuki coupling to construct the bisindole pyrrole skeleton. An evaluation of the biological activity of lynamicin D reveals that it has a minor effect on cell viability but it can modulate splicing of pre-mRNAs. We provide evidence that this effect is mainly due to the ability of lynamicin D to alter the levels of SRPK1, the key kinase involved in both constitutive and alternative splicing.

Isomeric chiral pyrrole diamides and their efficacy in enantioselective sensing of tartrate in sol–gel medium

Pyridinium motif-based chiral pyrrole diamide clefts 1 and 2 have been designed and synthesized for chiral recognition of hydroxycarboxylates in sol–gel medium. Of the two isomeric chiral receptors, receptor 1 shows selective sensing of D-tetrabutylammonium tartrate over its mirror image isomer in CH3CN. The isomeric receptor 2 did not show any enantioselectivity in the recognition. Moreover, the receptor 1 validates prompt visual sensing of D-tartrate through gelation. The recognition properties of the receptors have been studied by fluorescence, UV–vis,1H NMR and CD spectroscopic methods.

Synthesis and characterization of Boc-protected 4-amino- and 5-amino-pyrrole-2-carboxylic acid methyl esters

Syntheses of Boc-protected 4-amino- and 5-amino-pyrrole-2-carboxylic acid methyl esters have been achieved and the structures of these compounds have been fully characterized by detailed NMR studies.

Pyrrole-derivatives as factor Xa inhibitors

The present invention relates to compounds of the formulae I and Ia, wherein R0 ; R1 ; R2 ; R3 ; R4; R22, Q; V, G and M have the meanings indicated in the claims. The compounds of the formulae I and Ia are valuable pharmacologically active compounds. They exhibit a strong antithrombotic effect and are suitable for the therapy and prophylaxis of cardiovascular disorders like thromboembolic diseases or restenoses. They are reversible inhibitors of the blood clotting enzymes factor Xa (FXa) and/or factor VIIa (FVIIa), and can in general be applied in conditions in which an undesired activity of factor Xa and/or factor VIIa is present or for the cure or prevention of which an inhibition of factor Xa and/or factor VIIa is intended. The invention furthermore relates to processes for the preparation of compounds of the formulae I and Ia, their use, in particular as active ingredients in pharmaceuticals, and pharmaceutical preparations comprising them.

Carboxylate Binding by 2-(Guanidiniocarbonyl)pyrrole Receptors in Aqueous Solvents: Improving the Binding Properties of Guanidinium Cations through Additional Hydrogen Bonds

A series of guanidiniocarbonyl pyrrole receptors has been synthesized which bind carboxylates by ion pairing in combination with multiple hydrogen bonds. Their binding properties with various carboxylates have been investigated using NMR titration studies in 40% water/DMSO (ν/ν). The best receptor has association constants which are in the order of K ≈ 103 mol-1 and hence some 30 times larger than with the simple acetyl guanidinium cation. Through a systematic variation of the receptor structure, semiquantitative estimates for the energetic contributions of the individual binding interactions could be derived. These data show that the various hydrogen bonds are not equally important for the binding but differ significantly in their energetic contribution to the overall complexation process. Furthermore, the receptor can be made chiral and shows selectivity upon binding of enantiomeric amino acid carboxylates. Molecular modeling was used to obtain structural information for the various receptor carboxylate complexes and served as a basis to explain the observed differences in binding constants.

Highly stable self-association of 5-(guanidiniocarbonyl)-1H-pyrrole- 2carboxylate in DMSO - The importance of electrostatic interactions

The zwitteriomc compound 5-(guanidiniocarbonyl)-1H-pyrrole-2-carboxylate (1) self-assembles to form dimers, which are completely stable in DMSO even at 170 °C or at concentrations of 0.001 mM. This high stability stems from a combination of multiple weak interactions. NMR titrations of 1H-pyrrole-2- carboxylate (5) with (1H-pyrrole-2-carbonyl)-guanidinium (6) and [5- (methoxycarbonyl)-1H-pyrrole-2-carbonyl]guanidinium (8) led to binding constants of K ? 106 mol-1 in DMSO and K ? 103 mol-1 in 40% water/DMSO for carboxylate binding by the 2-(guanidiniocarbonyl)pyrrole moiety. The stability constant for the dimer 12 in DMSO could therefore be estimated as K ? 1012 mol-1. In solution, the self-association process of 1 can be completely disrupted by protonation of the carboxylate group. In the solid state, however, the hydrochloride salt 1+ also exists as a similar but only very weakly hydrogen-bonded dimer.

Side chain selective binding of N-acetyl-α-amino acid carboxylates by a 2-(guanidiniocarbonyl)pyrrole receptor in aqueous solvents

2-(Guanidiniocarbonyl)pyrrole 1 binds N-acetyl-α-amino acid carboxylates in 40% H2O-DMSO with binding constants ranging from K = 360 to 1700 mol-1 depending on the structure of the amino acid side chain.