3185-95-3

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-Cyanoethyl)-1-methyl-4-nitro-1H-pyrrole-2-carboxamide is used as a chemical intermediate for the synthesis of Netropsin Dihydrochloride (N390958), a DNA minor groove binding ligand. Its application is significant in the development of drugs that can interact with DNA, potentially leading to novel treatments for various diseases and conditions.
Used in Research and Development:
In the field of research and development, N-(2-Cyanoethyl)-1-methyl-4-nitro-1H-pyrrole-2-carboxamide is utilized as a key component in the synthesis of compounds with potential therapeutic applications. Its role in creating DNA minor groove binding ligands allows scientists to study and understand the interactions between these ligands and DNA, which can contribute to the advancement of targeted drug delivery systems and the development of new therapeutic strategies.

Uses

Given the provided materials, there are no explicit uses listed for N-(2-Cyanoethyl)-1-methyl-4-nitro-1H-pyrrole-2-carboxamide. However, based on its structural features, one can hypothesize potential applications in various industries, which would require further research and validation:
Used in Pharmaceutical Industry:
N-(2-Cyanoethyl)-1-methyl-4-nitro-1H-pyrrole-2-carboxamide could be used as a pharmaceutical intermediate for the synthesis of drugs targeting specific biological pathways. Its unique structure may allow it to interact with certain enzymes or receptors, making it a candidate for drug development.
Used in Chemical Research:
In the field of chemical research, N-(2-Cyanoethyl)-1-methyl-4-nitro-1H-pyrrole-2-carboxamide might serve as a subject for studying the effects of different functional groups on chemical reactivity and stability. Its synthesis and modification could provide insights into organic chemistry and the development of new synthetic methods.
Used in Material Science:
N-(2-Cyanoethyl)-1-methyl-4-nitro-1H-pyrrole-2-carboxamide could also be explored for its potential applications in material science, possibly as a component in the development of new polymers or as a dopant in electronic materials, given the presence of electron-withdrawing and electron-donating groups in its structure.

Upstream product

• 13138-76-6 1-methyl-4-nitropyrrole-2-carboxylic acid methyl ester 
• 21898-65-7 1-methyl-2-trichloroacetyl-1H-pyrrole 
• 96-54-8 N-Methylpyrrole 
• 13138-78-8 1-methyl-4-nitro-pyrrol-2-carboxylic acid 
• 6973-60-0 1-Methyl-2-pyrrolecarboxylic acid 
• 120122-47-6 1-methyl-4-nitro-2-trichloroacetylpyrrole 
• 352-96-5 3-aminopropionitrile fumarate salt 
• 151-18-8 2-cyanoethylamine 
• 28494-51-1 1-methyl-4-nitro-1H-pyrrole-2-carbonyl chloride 

Downstream Products

• 113598-28-0 (4S)-(+)-Anthelvencin A 
• 113598-34-8 (4R)-(-)-anthelvencin A 
• 123724-79-8 3-<1-methyl-4-<4-methyl-2-(1-methyl-4-(formylamino)-pyrrole-2-carboxamido)thiazole-5-carboxamido>pyrrole-2-carboxamido>propionamidine hydrochloride 
• 123724-82-3 3-<1-methyl-4-<2-<1-methyl-4-(formylamino)pyrrole-2-carboxamido>thiazole-4-carboxamido>pyrrole-2-carboxamido>propionamidine hydrochloride 
• 123724-77-6 3-<1-methyl-4-(2-(formylamino)-4-methylthiazole-5-carboxamido)pyrrole-2-carboxamido>propionamidine hydrochloride 
• 123724-80-1 3-<1-methyl-4-(2-(formylamino)thiazole-4-carboxamido)-pyrrole-2-carboxamido>propionamidine hydrochloride 
• 142211-78-7 3-<1-methyl-4-<1-methyl-4-<1-methyl-4-(formylamino)pyrrole-2-carboxamido>imidazole-2-carboxamido>pyrrole-2-carboxamido>propionamidine hydrochloride 
• 111136-84-6 (4R)-(-)-dihydrokikumycin B 
• 111136-83-5 (4S)-(+)-dihydrokikumycin B 
• 14665-05-5 3-<4-(4-aminobenzenecarboxamido)-1-methylpyrrole-2-carboxamido>propiononitrile 
• 3786-88-7 1-methyl-4-<1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido>pyrrole-2-carboxamidopropionamidine hydrochloride 
• 6576-51-8 distamycin A hydrochloride 
• 18133-23-8 netropsin sulfate 
• 97950-75-9 3-<1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido>propionamidine hydrochloride 

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.

Synthesis of geometrically constrained unsymmetrical bis(polyamides) related to the antiviral distamycin

Analysis of the structural and stereochemical requirements for the strict DNA base-sequence recognition of (AT)4 and (AT)5, respectively, for the oligopeptide minor-groove binding agents netropsin (I) and distamycin (II) leads to proposals for the rational structure modification for altered base recognition. In this paper we report the synthesis of unsymmetrical imidazo-pyrrolo-bis(polyamides), structurally related to the natural antiviral agents distamycin, and bearing either unnatural (25-27) or natural (31-33) termini linked by a flexible or rigid linker. This is the first report of the synthesis of an imidazole-bearing structure with either dimethylaminopropyl or amidinium termini in the linked bis(polyamides).

The Synthesis of Radiosensitizers Designed to Bind to the Minor Groove of Duplex DNA

The synthesis is described of novel compounds, 17, 21, 25 and 27, containing in their molecular architecture both a terminal nitroarene component and an oligopeptide similar to that in the antibiotic distamycin, which is known to bind into the minor groov

Synthesis, DNA binding, and biological evaluation of synthetic precursors and novel analogues of netropsin

A series of oligopeptides have been synthesized that are structurally related to the natural agent netropsin. The binding constants to double-stranded polynucleotides as well as the cytostatic activity against both murine human tumor cell lines and the in

Efficient synthesis of oligo-N-methylpyrrolecarboxamides and related compounds

1-Methyl-4-nitro-2-trichloroacetylpyrrole 5, a new precursor for the syntheses of oligo-N-methylpyrrolecarboxamide antibiotics and their analogues, was prepared with facility. The versatility of 5 was demonstrated by the syntheses of oligopeptides 16-19.

Efficient Total Syntheses of the Oligopeptide Antibiotics Netropsin and Distamycin

New and efficient total syntheses of the natural oligopeptide antiviral antibiotics netropsin and distamycin are described.These procedures feature a different strategy of introduction of the terminal groups from that used hitherto, high yield coupling steps, improvements in the Pinner reaction for introducing the amidine moiety, and the novel use of N-formylimidazole for introduction of the formyl moiety in distamycin.The methods also avoid column chromatography with the attendant contamination of the oligopeptide hydrochlorides with inorganic salts eluted from adsorbents.The synthetic procedures are general and may be adapted to the synthesis of related oligopeptide structures.