5930-93-8

Usage

Uses

Used in Organic Synthesis:
4-Nitropyrrole-2-carboxylic acid is used as a key intermediate in organic synthesis for the preparation of various pharmaceuticals and agrochemicals. Its nitro group makes it a versatile component in chemical reactions, contributing to the synthesis of a wide range of compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Nitropyrrole-2-carboxylic acid is utilized as a building block for the synthesis of heterocyclic compounds, which are essential in the development of new drugs. Its unique structure and reactivity allow for the creation of molecules with specific therapeutic properties.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 4-Nitropyrrole-2-carboxylic acid serves as a precursor in the synthesis of compounds with pesticidal or herbicidal properties, contributing to the development of more effective and targeted crop protection agents.
Safety Considerations:
It is important to handle 4-Nitropyrrole-2-carboxylic acid with care due to its known toxicity if ingested or inhaled, necessitating proper safety measures during its use in laboratories and industrial settings.

InChI:InChI=1/C5H4N2O4/c8-5(9)4-1-3(2-6-4)7(10)11/h1-2,6H,(H,8,9)

Upstream product

• 32116-24-8 5-acetyl-3-nitro-1H-pyrrole 
• 7732-18-5 water 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 634-97-9 pyrrole-2-carboxyl acid 
• 35302-72-8 pyrrol-2-yl trichloromethyl ketone 
• 879369-38-7 nitromalondialdehyde monohydrate 
• 459-73-4 GlyOEt*HCl 
• 1072-83-9 2-Acetylpyrrole 
• 53391-50-7 2,2,2-trichloro-1-(4-nitro-1H-pyrrol-2-yl)ethan-1-one 
• 5930-92-7 Ethyl 4-nitropyrrole-2-carboxylate 
• 13138-74-4 methyl 4-nitropyrrole-2-carboxylate 

Downstream Products

• 265664-80-0 {4-[(4-nitro-1H-pyrrole-2-carbonyl)-amino]-benzyl}-carbamic acid tert-butyl ester 
• 945255-45-8 C₃₇H₅₇N₇O₈ 
• 664341-83-7 C₄₈H₆₁N₉O₂₃ 
• 664341-82-6 C₄₉H₆₂N₈O₂₃ 

Relevant academic research and scientific papers

Novel non-steroidal/non-anilide type androgen antagonists: Discovery of 4-substituted pyrrole-2-carboxamides as a new scaffold for androgen receptor ligands

We designed and synthesized novel pyrrole-2-carboxamide derivatives as androgen antagonists. Compounds 10 and 13 bearing benzylamine or aniline at the 4-position of the pyrrole ring showed moderate androgen antagonistic activity, and inhibited the androgen-dependent growth of Shionogi carcinoma cells (SC-3). Study of the structure-activity relationships of compound 13 led to a potent androgen antagonist 36, which has higher affinity than flutamide (4) for androgen nuclear receptor (AR). Thus, pyrrole-2-carboxamide is a new scaffold for developing AR antagonists.

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.

Method for the synthesis of pyrrole and imidazole carboxamides on a solid support

The present invention describes a novel method for the solid phase synthesis of polyamides containing imidazole and pyrrole carboxamides. The polyamides are prepared on a solid support from aromatic carboxylic acids and aromatic amines with high stepwise coupling yields (>99%), providing milligram quantities of highly pure polyamides. The present invention also describes the synthesis of analogs of the natural products Netropsin and Distamycin A, two antiviral antibiotics. The present invention also describes a novel method for the solid phase synthesis of imidazole and pyrrole carboxamide polyamide-oligonucleotide conjugates. This methodology will greatly increase both the complexity and quantity of minor-groove binding polyamides and minor-groove binding polyamide-oligonucleotide conjugates which can be synthesized and tested.

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.