13138-74-4

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
Methyl 4-nitro-1H-pyrrole-2-carboxylate is utilized as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structural motifs and reactivity contribute to the development of new compounds with therapeutic and pesticidal properties.
Used in Organic Synthesis:
As a building block in organic synthesis, methyl 4-nitro-1H-pyrrole-2-carboxylate is employed for the preparation of heterocyclic compounds. Its versatile chemical properties allow for the creation of a wide range of complex organic molecules with potential applications in various fields.
Used in Antibacterial and Antifungal Applications:
Methyl 4-nitro-1H-pyrrole-2-carboxylate exhibits moderate to high antibacterial and antifungal activity, making it a valuable compound in the development of new antimicrobial agents. Its potential use in combating drug-resistant pathogens highlights its importance in the field of infectious disease research and treatment.
Used in Chemical Research:
In the realm of chemical research, methyl 4-nitro-1H-pyrrole-2-carboxylate serves as a valuable tool for studying the properties and reactions of nitro-substituted pyrrole derivatives. Its diverse reactivity allows researchers to explore new synthetic pathways and develop innovative applications in various chemical processes.

InChI:InChI=1/C6H6N2O4/c1-12-6(9)5-2-4(3-7-5)8(10)11/h2-3,7H,1H3

Upstream product

• 40824-82-6 nitromalonic aldehyde 
• 616-34-2 methoxycarbonylmethylamine 
• 53391-41-6 2,2,2-trichloro-1-(5-nitro-1H-pyrrol-2-yl)ethan-1-one 
• 53391-50-7 2,2,2-trichloro-1-(4-nitro-1H-pyrrol-2-yl)ethan-1-one 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 120122-47-6 1-methyl-4-nitro-2-trichloroacetylpyrrole 
• 35302-72-8 pyrrol-2-yl trichloromethyl ketone 
• 1193-62-0 methyl Pyrrole-2-carboxylate 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 34461-00-2 nitromalondialdehyde sodium salt 

Downstream Products

• 5930-93-8 4-nitropyrrole-2-carboxylic acid 
• 1263419-21-1 6-amino-4-((1S,2R)-2-methylcyclohexylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide 
• 1263419-22-2 4-((1R,2S)-2-methylcyclohexylamino)-6-nitropyrrolo[1,2-b]pyridazine-3-carbonitrile 
• 1263419-23-3 4-((1R,2S)-2-methylcyclohexylamino)-6-nitropyrrolo[1,2-b]pyridazine-3-carboxamide 
• 1263419-24-4 6-amino-4-((1R,2S)-2-methylcyclohexylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide 
• 1263419-65-3 6-nitro-4-(phenylamino)pyrrolo[1,2-b]pyridazine-3-carbonitrile 
• 1263419-66-4 6-nitro-4-(phenylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide 
• 1263419-67-5 6-amino-4-(phenylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide 
• 1263419-74-4 4-(2-methylcyclohexylamino)-6-nitropyrrolo[1,2-b]pyridazine-3-carbonitrile 
• 1263419-75-5 4-(2-methylcyclohexylamino)-6-nitropyrrolo[1,2-b]pyridazine-3-carboxamide 
• 1263419-76-6 6-amino-4-(2-methylcyclohexylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide 
• 1263419-19-7 4-((1S,2R)-2-methylcyclohexylamino)-6-nitropyrrolo[1,2-b]pyridazine-3-carbonitrile 
• 1263419-20-0 4-((1S,2R)-2-methylcyclohexylamino)-6-nitropyrrolo[1,2-b]pyridazine-3-carboxamide 
• 1245644-73-8 6-nitropyrrolo[2,1-f][1,2,4]triazine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

Design, synthesis, DNA-binding and cytotoxicity evaluation of new potential combilexines

Combilexines, compounds in which a DNA intercalator is linked to a minor groove binding component, interact with the DNA in a sequence specific manner to yield in most cases compounds with anticancer activity. A series of new compounds closely related to netropsin in which the two components were linked by an amide group was synthesised as potential combilexines. As some of these compounds showed cytotoxic activity in vitro, an attempt was made to rationalise their mechanism of action. The DNA binding characteristics of the carboxamides were evaluated by thermal denaturation experiments and by ethidium bromide displacement assay. Their ability to inhibit the topoisomerase I was also determined. It was concluded that the new compounds were only weak DNA ligands although able in some cases to inhibit topoisomerase I.

TGF BETA RECEPTOR ANTAGONISTS

The invention relates generally to compounds that modulate the activity of TGFβR-1 and TGFβ R-2, pharmaceutical compositions containing said compounds and methods of treating proliferative disorders and disorders of dysregulated apoptosis, such as cancer, utilizing the compounds of the invention.

A sweet origin for the key congocidine precursor 4-acetamidopyrrole-2- carboxylate

Feeding (Streptomyces) frenzy: Natural products belonging to the pyrrolamide family are defined by their pyrrole-2-carboxamide moiety. 4-acetamidopyrrole-2-carboxylate is identified as the key pyrrolamide congocidine precursor (see scheme) through feeding studies using Streptomyces ambofaciens. The biosynthetic pathway of congocidine starts with the carbohydrate N-acetylglucosamine and involves carbohydrate-processing enzymes. Copyright

HETEROCYCLIC COMPOUNDS AS JANUS KINASE INHIBITORS

The invention provides compounds of formula I: or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods for suppressing an immune response or treating cancer or a hematologic malignancy using compounds of formula I.

PYRROLO [1, 2-B] PYRIDAZINE DERIVATIVES AS JANUS KINASE INHIBITORS

The invention provides compounds of formula l: ( I ) or a salt thereof as described herein. The invention also provides pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods for suppressing an immune response or treating cancer or a hematologic malignancy using compounds of formula I.

New guanidinium-based carboxylate receptors derived from 5-amino-pyrrole-2-carboxylate: Synthesis and first binding studies

The syntheses of two new guanidinium-based carboxylate receptors 2a,b derived from 5-amino pyrrole-2-carboxylate 4 are described. These receptors bind N-acetyl alanine carboxylate and O-acetyl lactate efficiently in aqueous DMSO as could be shown by NMR studies. However, compared to previously reported guanidiniocarbonyl pyrrole receptors 1, the reversal in the direction of the amide group in 2a,b changes both the substrate selectivity (amides are now preferred over esters) and their relative binding affinities. Both effects can be explained based on the calculated complex structure.

Design, synthesis and in vitro cytotoxicity studies of novel pyrrolo [2,1][1,4] benzodiazepine-glycosylated pyrrole and imidazole polyamide conjugates

The design, synthesis and biological evaluation of novel pyrrolo [2,1][1,4] benzodiazepine-water insoluble 31-38 and water soluble 39-46 glycosylated pyrrole and imidazole polyamide conjugates are described that involved mercuric chloride mediated cyclization of the corresponding amino diethyl thioacetals. The compounds were prepared with varying numbers of pyrrole and imidazole containing polyamides and incorporating glucose moieties in order to improve the water solubility of PBD-polyamide conjugates and probe the structural requirements for optimal in vitro antitumor activity. These compounds were tested against a panel of 60 human cancer cells by the National Cancer Institute, and demonstrated that the water soluble PBD-polyamide compounds exhibited a higher level of cytotoxic activity than the existing natural and synthetic pyrrolo [2,1-c][1,4] benzodiazepines. The cytotoxic activities of these compounds dramatically increase after hydrolysis of their acetylated counterparts. The activity data summarized in Table 1 and Table 2 show that the solubility of the PBD-polyamides and also the type of heterocycle play important roles influencing the cytotoxic activity of the PBD-polyamide conjugates. The PBD-glycosylated polyamide (water soluble) conjugates 39-46 are highly cytotoxic against many human cancer cell lines in comparison with the PBD-polyamide (water insoluble version) conjugates.

Synthesis, DNA binding, topoisomerases inhibition and cytotoxic properties of 4-arylcarboxamidopyrrolo-2-carboxyanilides

Three 4-arylcarboxamidopyrrolo-2-carboxyanilides bearing different substituents on the pyrrole nitrogen were synthesized and evaluated for their capacities to bind to specific sequences within the minor groove of DNA and to inhibit human topoisomerases I and II in vitro. The cytotoxicity of the drugs correlates with their DNA binding affinities. The two drugs bearing a N-methyl or N-benzyl pyrrole stabilize topoisomerase I-DNA complexes. (C) 2000 Elsevier Science Ltd. All rights reserved.

Complex formation between dsDNA and pyrrole imidazole polyamides

Methods and compositions are provided for forming complexes between dsDNA and oligomers of heterocycles, aliphatic amino acids, particularly omega-amino acids, and a polar end group. By appropriate choice of target sequences and composition of the oligomers, complexes are obtained with low dissociation constants. The formation of complexes can be used for identification of specific dsDNA sequences, for inhibiting gene transcription, and as a therapeutic for inhibiting proliferation of undesired cells or expression of undesired genes.

Polyaromatic amide compounds and pharmaceutical/cosmetic compositions comprised thereof

Novel pharmaceutically/cosmetically-active polyaromatic amides have the structural formula (I): STR1 wherein Z is a radical --CO--NH-- or --NH--CO--, and are useful for the treatment of a wide variety of disease states, whether human or veterinary, for example dermatological, rheumatic, respiratory, cardiovascular and ophthalmological disorders, as well as for the treatment of mammalian skin and hair conditions/disorders.