120122-47-6

Basic information

• Product Name: 1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-PYRROLE
• Synonyms: 2,2,2-TRICHLORO-1-(1-METHYL-4-NITRO-1H-PYRROL-2-YL)-ETHANONE;1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-PYRROLE;N-METHYL-4-NITRO-2-TRICHLOROACETYLPYRROLE;2-Trichloro-1-(1-methyl-4-nitro-1H-pyrrol-2-yl)ethanone;2,2,2-Trichloro-1-(1-methyl-4-nitro-1H-pyrrol-2-yl;1-methyl-4-nitro-2-trichloroacetyl pyrrole;2-(Trichloroacetyl)-1-methyl-4-nitropyrrole;4-Nitro-2-(trichloroacetyl)-N-methylpyrrole
• CAS NO: 120122-47-6
• Molecular Formula: C₇H₅Cl₃N₂O₃
• Molecular Weight: 271.49
• Mol File: 120122-47-6.mol
• Article Data: 27

Chemical Properties

• Melting Point: 132-135°C
• Boiling Point: 319.1 °C at 760 mmHg
• Flash Point: 146.8 °C
• Appearance: /
• Density: 1.66
• Vapor Pressure: 0.000345mmHg at 25°C
• Refractive Index: 1.616
• Storage Temp.: -15°C
• PKA: -15.07±0.70(Predicted)
• CAS DataBase Reference: 1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-PYRROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-PYRROLE(120122-47-6)
• EPA Substance Registry System: 1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-PYRROLE(120122-47-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 120122-47-6(Hazardous Substances Data)

Usage

Description

1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-PYRROLE is a chemical compound characterized by its unique molecular structure, which features a pyrrole ring with a methyl group at the 1st position, a nitro group at the 4th position, and a trichloroacetyl group at the 2nd position. 1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-PYRROLE is known for its potential applications in various fields due to its chemical properties.

Uses

1. Used in Chemical Research:
1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-PYRROLE is used as a chemical intermediate for the synthesis of various complex organic molecules. Its unique structure allows it to be a valuable building block in the development of new compounds with specific properties and applications.
2. Used in Pharmaceutical Industry:
1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-PYRROLE is used as a key component in the development of novel drugs. Its chemical properties make it a promising candidate for the creation of new therapeutic agents, particularly in the areas of cancer treatment and other diseases.
3. Used in DNA-binding Studies:
1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-PYRROLE is used as a starting material to develop DNA-binding TEMPO derivatives. These derivatives are essential for evaluating nuclear oxidative stress, which is a critical factor in understanding the mechanisms of various diseases and the development of potential treatments.
4. Used in Material Science:
1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-PYRROLE can be utilized in the development of new materials with specific properties, such as improved stability, reactivity, or selectivity. Its unique structure and chemical properties make it a valuable component in the design and synthesis of advanced materials for various applications.

InChI:InChI=1/C7H5Cl3N2O3/c1-11-3-4(12(14)15)2-5(11)6(13)7(8,9)10/h2-3H,1H3

Upstream product

• 21898-65-7 1-methyl-2-trichloroacetyl-1H-pyrrole 
• 96-54-8 N-Methylpyrrole 
• 35302-72-8 pyrrol-2-yl trichloromethyl ketone 
• 76-02-8 trifluoroacetyl chloride 

Downstream Products

• 3185-95-3 1-methyl-4-nitro-1H-pyrrole-2-carboxylic acid (2-cyanoethyl)amide 
• 132553-01-6 1-Methyl-4-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-1H-pyrrole-2-carboxylic acid benzyl ester 
• 132553-02-7 1-Methyl-4-({1-methyl-4-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-1H-pyrrole-2-carbonyl}-amino)-1H-pyrrole-2-carboxylic acid benzyl ester 
• 132584-70-4 1-Methyl-4-{[1-methyl-4-({1-methyl-4-[(1-methyl-4-nitro-1H-pyrrole-2-carbonyl)-amino]-1H-pyrrole-2-carbonyl}-amino)-1H-pyrrole-2-carbonyl]-amino}-1H-pyrrole-2-carboxylic acid benzyl ester 
• 67973-92-6 1-methyl-4-nitropyrrole-2-carboxanilide 
• 120095-66-1 benzyl 1-methyl-4-nitropyrrole-2-carboxylate 
• 13138-76-6 1-methyl-4-nitropyrrole-2-carboxylic acid methyl ester 
• 67974-08-7 1-methyl-4-nitro-1H-pyrrole-2-carboxylic acid tert-butyl ester 
• 682748-53-4 1-methyl-4-nitro-1H-pyrrole-2-carboxylic acid (2-amino-phenyl)-amide 
• 794529-77-4 [(4-amino-1-methyl-1H-pyrrole-2-carbonyl)-amino]-acetic acid methyl ester 

Relevant articles and documents

Design and Synthesis of Novel Thiazole-Containing Cross-Linked Polyamides Related to the Antiviral Antibiotic Distamycin

A family of naturally occurring oligopeptides includes netropsin, distamycin, anthelvencin, kikumycin B, amidinomycin, and norformycin. Netropsin (I) and distamycin (II) express their biological activities by targeting specific sequences of chemical functionalities in the minor groove of DNA. Both netropsin and distamycin can be regarded as polyamide chains in which each α-carbon has been replaced by a five-membered pyrrole ring. The repeat distance in such an augmented polyamide chain is almost the same as the distance from one base pair to the next along the floor of a minor groove within β-DNA. In this paper we report the synthesis of 16-21 cross-linked polyamides containing a thiazole heterocyclic ring bearing the active functionalites NH2, NHCHO, or H. 16 and 17 were synthesized by DCC and HOBt catalyzed reaction of 5 with 14 and 15, while the formylation products 18 and 19 were obtained by coupling the formylated 4-methyl-thiazolated acid 6 with 14 and 15. The deaminated compounds 20 and 21 were obtained by the coupling of 5-trichloroacetyl-4-methylthiazole 7 synthesized from 4-methylthiazole. All the six cross-linked polyamides 16-21 were tested for their DNA gyrase inhibition. The studies have shown these polyamides have better sequence recognition and a greater percentage of inhibition than the corresponding monomers. The compound 17 shows complete inhibition of gyrase at 0.5 μM concentration as compared to the naturally occurring distamycin at 1.0 μM.

Bromoacetophenone-based photonucleases: photoinduced cleavage of DNA by 4'-bromoacetophenone-pyrrolecarboxamide conjugates.

[formula: see text] 4'-Bromoacetophenone derivatives which upon excitation can generate monophenyl radicals capable of hydrogen atom abstraction were investigated as photoinducible DNA cleaving agents. Pyrrolecarboxamide-conjugated 4'-bromoacetophenones were synthesized, and their DNA cleaving activities and sequence selectivities were determined.

Synthesis, anti-mycobacterial activity and DNA sequence-selectivity of a library of biaryl-motifs containing polyamides

The alarming rise of extensively drug-resistant tuberculosis (XDR-TB) strains, compel the development of new molecules with novel modes of action to control this world health emergency. Distamycin analogues containing N-terminal biaryl-motifs 2(1-5)(1-7)

Synthesis of lipid derivatives of pyrrole polyamide and their biological activity

Novel fatty acyl and phospholipid derivatives of pyrrole polyamide were synthesized. Their cytotoxicity against a cancer cell line of MT-4 cells and those infected by human immunodeficiency virus (HIV) was examined. Although no anti-HIV activity was found, their cytotoxicitty against the cancer cells was significantly enhanced by introducing a lipophilic group into the pyrrole polyamide.

Series of oligopolyamide containing N-methylpyrrole and N-methylimidazole and synthesis method thereof

The invention discloses a series of oligopolyamide DNA minor groove ligand compounds containing N-methylpyrrole and N-methylimidazole and a synthesis method thereof. The synthesis method provided by the invention adopts a five-membered heterocyclic compound and a derivative thereof as the raw materials, and carries out a series of reactions like acylation, nitration, hydrogenation, condensation, hydrolysis and the like to synthesize the target product. The synthesis method provided by the invention is also applicable to synthesis of polyamide. The synthetic process adopted by the method provided by the invention has the characteristics of simple operation and high yield, and is suitable for industrial scale production. The oligopolyamide DNA minor groove ligand compounds containing N-methylpyrrole and N-methylimidazole provided by the invention have structural formulas shown as formula I and formula II in the specification.

DNA BINDING AGENTS WITH A MINOR GROOVE BINDING TAIL

Provided herein are compounds which intercalate into the DNA of a cell and are capable of crossing the blood brain barrier of a formula provided herein. Pharmaceutical compositions of the compounds and methods of treating cancer, for example brain, lung,