7126-51-4

Usage

Uses

Used in Organic Chemistry Research:
5-Formyl-1H-pyrrole-2-carboxylic acid is used as a research compound for its unique structural features, facilitating the study of pyrrole chemistry and its potential applications in the synthesis of complex organic molecules.
Used in Medicinal Chemistry Research:
As a derivative of pyrrole, 5-Formyl-1H-pyrrole-2-carboxylic acid is utilized as a key intermediate in the development of novel pharmaceuticals, given its potential to contribute to the creation of bioactive molecules with therapeutic properties.
Used in Drug Discovery:
5-Formyl-1H-pyrrole-2-carboxylic acid is employed as a precursor in the synthesis of various pharmaceuticals, leveraging its chemical reactivity and structural attributes to produce compounds with potential medicinal value.
Used in the Development of Bioactive Molecules:
5-Formyl-1H-pyrrole-2-carboxylic acid is used as a building block in the creation of bioactive molecules, capitalizing on its ability to be modified and incorporated into diverse molecular frameworks with potential biological activities.
Used in Pharmaceutical Synthesis:
5-Formyl-1H-pyrrole-2-carboxylic acid is utilized as a starting material in the synthesis of pharmaceuticals, particularly those with anti-inflammatory and antioxidant properties, due to its inherent biological activity and chemical versatility.

InChI:InChI=1/C6H5NO3/c8-3-4-1-2-5(7-4)6(9)10/h1-3,7H,(H,9,10)

Upstream product

• 7126-50-3 ethyl 5-formyl-1H-pyrrole-2-carboxylate 
• 1197-13-3 methyl 5-formyl-1H-pyrrole-2-carboxylate 
• 55314-16-4 (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one 
• 350-03-8 methyl-3-pyridylketone 
• 1193-62-0 methyl Pyrrole-2-carboxylate 
• 2199-43-1 ethyl 1H-pyrrole-2-carboxylate 

Downstream Products

• 446024-24-4 N-(5-formyl-1H-pyrrole-2-carbonyl)-L-phenylalanine methyl ester 
• 635313-73-4 N-(5-formyl-1H-pyrrole-2-carbonyl)-L-phenylalanyl-L-leucine methyl ester 
• 863201-78-9 2-benzyloxycarbonylamino-3-[(5-guanidinocarbonyl-1H-pyrrol-2-ylmethyl)-amino]-propionic acid methyl ester 
• 863201-70-1 C₂₄H₃₂N₆O₇ 
• 446024-27-7 2-[(6-benzyl-5-oxo-5H-pyrrolizine-3-carbonyl)-amino]-4-methyl-pentanoic acid methyl ester 
• 1198-75-0 methyl 5-formyl-1-methyl-1H-pyrrole-2-carboxylate 
• 1236291-25-0 (Z)-5-{6-[3-(4-methoxyphenyl)-ureido]-2-oxo-1,2-dihydroindol-3-ylidene-methyl}-1H-pyrrole-2-carboxylic acid 
• 1353644-02-6 C₃₃H₂₉F₃N₆O₄ 

Relevant academic research and scientific papers

Amino acid binding in water by a new guanidiniocarbonyl pyrrole dication: The effect of the experimental conditions on complex stability and stoichiometry

The synthesis and binding properties of a new guanidiniocarbonyl pyrrole dication 2 are reported, which efficiently binds alanine carboxylate with log Kass = 3.9 in buffered water. Due to the increased charge density in this dication, the binding constant is five times larger than for the parent guanidiniocarbonyl pyrrole monocation 1 (log K = 3.2). However, the experimental conditions for determining the binding constant significantly influence both complex stability and stoichiometry. With increasing amount of substrate added during the titration, the overall complex stability decreases due to the increasing ionic strength of the solution. Furthermore, the formation of 1:2 complexes between 2 and 7 becomes increasingly important. Therefore, for the comparison of binding data it has to be assured that exactly the same experimental conditions are used for their determination.

The synthesis and P388 cytotoxicity of mycalazol 11 and related 5-acyl- 2-hydroxymethylpyrroles

We report a general method for the synthesis of mycalazol 11 and some mimed 5-acyl-2-hydroxymethylpyrroles using a Stille coupling of 5-(tri-n- butylstannyl)pyrrole-2-carboxaldehyde with an acid chloride as the key step. The newly prepared 5-acyl-2-hydroxymethylpyrroles 5-7, together with the 5- carboxamido-2-hydroxymethylpyrrole 10, have been assayed for in vitro cytotoxicity against the P388 murine leukemia cell line.

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.

SPIRO-SUBSTITUTED OXINDOLE DERIVATIVES HAVING AMPK ACTIVITY

The present invention relates to compounds of formula (I), which have valuable pharmacological properties, in particular are activators of AMPK and which are therefore useful in the treatment of certain disorders that can be prevented or treated by activation of this receptor. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

OLEFIN SUBSTITUTED OXINDOLES HAVING AMPK ACTIVITY

The present invention relates to compounds of formula (I), which have valuable pharmacological properties, in particular are activators of AMPK and which are therefore useful in the treatment of certain disorders that can be prevented or treated by activation of this receptor. The compounds are suitable for treatment and prevention of diseases which can be influenced by this receptor, such as metabolic diseases, in particular diabetes type 2.

A facile and efficient multi-gram synthesis of N-protected 5-(guanidinocarbonyl)-1H-pyrrole-2-carboxylic acids

The synthesis of two versatile building blocks for supramolecular anion binding motifs, 5-(N-Boc-guanidinocarbonyl)-1H-pyrrole-2-carboxylic acid (1) and 5-(N-Cbz-guanidinocarbonyl)-1H-pyrrole-2-carboxylic acid (2) is reported. Using these building blocks, a guanidiniocarbonyl-pyrrole anion binding site can easily be introduced into more complex molecules by using standard amide coupling conditions. Both syntheses can be performed on a multi-gram scale. The products are obtained in pure form and can be stored as solids without decomposition. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis, biological evaluation and molecular modelling of N-heterocyclic dipeptide aldehydes as selective calpain inhibitors

A series of N-heterocyclic dipeptide aldehydes 4-13 have been synthesised and evaluated as inhibitors of ovine calpain 1 (o-CAPN1) and ovine calpain 2 (o-CAPN2). 5-Formyl-pyrrole 9 (IC50 values of 290 and 25 nM against o-CAPN1 and o-CAPN2, respectively) was the most potent and selective o-CAPN2 inhibitor, displaying >11-fold selectivity. The amino acid sequences of o-CAPN1 and o-CAPN2 have been determined. Because of the lack of available structural information on the ovine calpains, in silico homology models of the active site cleft of o-CAPN1 and o-CAPN2 were developed based on human calpain 1 (h-CAPN1) X-ray crystal structure (PDB code 1ZCM). These models were used to rationalise the observed SAR for compounds 4-13 and the selectivity observed for 9. The o-CAPN2 selective inhibitor 9 (CAT0059) was assayed in an in vitro ovine lens culture system and shown to successfully protect the lens from calcium-induced opacification.

Sulfonamide substituted indolinones as inhibitors of DNA dependent protein kinase (DNA-PK)

The present invention relates generally to the field of radiosensitizing agents which are capable of enhancing radiotherapy by inhibiting DNA-PK (DNA-protein kinase). In particular, it relates to sulfonamide substituted indolinones which inhibit DNA-PK.

Ring-deactivated hydroxyalkylpyrrole-based inhibitors of α-chymotrypsin: Synthesis and mechanism of action

13C NMR and mass spectrometry studies have been used to demonstrate that the inhibition of α-chymotrypsin by N-sulfonylhydroxymethylpyrrole inhibitors (10) is non-covalent. Hydroxyalkylpyrroles in which an electron-withdrawing group (acyl substituent) is introduced at the alternative C2 position have been synthesised and also shown to inactivate α-chymotrypsin. SAR studies on this class suggests that the incorporation of phenylalanine at C2 is favoured, however, there is little gain in introducing a hydrophobic substituent at C5.

Rational design of 4,5-disubstituted-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-ones as a novel class of inhibitors of epidermal growth factor receptor (EGF-R) and Her2(p185(erbB)) tyrosine kinases.

A novel class of 4,5-disubstituted-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-ones has been discovered as potent and selective inhibitors of the EGF-R tyrosine kinase family. These compounds selectively inhibit EGF-R kinase activity at low nanomolar concentration and tyrosine autophosphorylation in cells expressing EGF-R or Her2 (p185(erbB)). Structure-activity relationships (SARs) for this class of compounds are presented.