120095-64-9

Usage

Uses

Used in Pharmaceutical Industry:
1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-IMIDAZOLE is used as an intermediate in the synthesis of DNA-recognizing polyamides. These polyamides are designed to bind to specific DNA sequences, which can be utilized for targeted drug delivery and gene regulation. The compound's ability to interact with DNA makes it a valuable component in the development of novel therapeutic strategies for various diseases, including cancer.
Used in Chemical Synthesis:
1-METHYL-4-NITRO-2-(TRICHLOROACETYL)-1H-IMIDAZOLE can also be used as a building block in the synthesis of other complex organic molecules. Its unique structure allows for further functionalization and modification, making it a versatile starting material for the development of new compounds with potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 30148-23-3 2-trichloroacetyl-1-methylimidazole 

Downstream Products

• 109012-23-9 ethyl 1-methyl-4-nitroimidazole-2-carboxylate 
• 169770-25-6 1-methyl-4-nitro-1H-imidazole-2-carboxylic acid methyl ester 
• 179983-49-4 tert-butyl 4-nitro-N-methyl-1H-imidazole-2-carboxylate 
• 373362-10-8 3-(4-{[4-(4-{2-[5-(2-carboxy-vinyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-imidazol-4-ylcarbamoyl}-benzoylamino)-1-methyl-1H-imidazole-2-carbonyl]-amino}-1-methyl-1H-pyrrol-2-yl)-acrylic acid 
• 373362-06-2 3-(4-{[4-(4-{2-[5-(2-ethoxycarbonyl-vinyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-imidazol-4-ylcarbamoyl}-benzoylamino)-1-methyl-1H-imidazole-2-carbonyl]-amino}-1-methyl-1H-pyrrol-2-yl)-acrylic acid ethyl ester 
• 373362-17-5 N,N'-bis-{2-[5-(3-imidazol-1-yl-3-oxo-propenyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-imidazol-4-yl}-terephthalamide 
• 162085-97-4 methyl 4-amino-1-methyl-1H-imidazole-2-carboxylate 
• 1176170-67-4 N-(4-(dimethylamino)phenyl)-1-methyl-4-nitro-1H-imidazole-2-carboxamide 
• 109012-24-0 1-methyl-4-nitro-1H-imidazole-2-carboxylic acid 
• 128293-65-2 benzyl 4-((tert-butoxycarbonyl)amino)-1-methyl-1H-imidazole-2-carboxylate 
• 537049-66-4 4-(1-methylpyrrole-2-carboxamido)-1-methylimidazole-2-carboxylic acid 
• 252206-28-3 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-1-methyl-1H-imidazole-2-carboxylic acid 
• 288624-04-4 C₄₇H₄₇N₁₉O₈ 
• 288623-94-9 N-(2-{2-[2-(3-dimethylamino-propylcarbamoyl)-1-methyl-1H-imidazol-4-ylcarbamoyl]-1-methyl-1H-imidazol-4-ylcarbamoyl}-1-methyl-1H-imidazol-4-yl)-terephthalamic acid 

Relevant academic research and scientific papers

4-Methyltrityl-Protected Pyrrole and Imidazole Building Blocks for Solid Phase Synthesis of DNA-Binding Polyamides

DNA-binding polyamides are synthetic oligomers of pyrrole/imidazole units with high specificity and affinity for double-stranded DNA. To increase their synthetic diversity, we report a mild methodology based on 4-methyltrityl (Mtt) solid phase peptide synthesis (SPPS), whose building blocks are more accessible than the standard Fmoc and Boc SPPS ones. We demonstrate the robustness of the approach by preparing and studying a hairpin with all precursors. Importantly, our strategy is orthogonal and compatible with sensitive molecules and could be readily automated.

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.

Synthesis of DNA-sequence-selective hairpin polyamide platinum complexes

Two DNA-sequence-selective hairpin polyamide platinum(II) complexes, containing pyrrole and imidazole heterocyclic rings, have been synthesised by different methods. A six-ring complex, selective for (A/T)GGG-(A/T) DNA sequences, was made by using solid-phase synthesis, whilst an eight-ring complex, selective for (A/ T)CCTG(A/T) DNA sequences, was made by utilising standard wet chemistry. Solid-phase synthesis resulted in a significantly higher yield, required less purification and is more efficient than the wet synthesis; as such, it is the preferred method for further work. The metal complexes were characterised by 1H and 195Pt NMR spectroscopy and ESI mass spectrometry. The two compounds provide a foundation for the synthesis of more complex molecules containing multiple hairpins and/or platinum groups.

Method of the solid phase synhesis of pyrrole-imidazole polyamide

It is intended to provide a method of producing a pyrrole-imidazole polyamide whereby a longer pyrrole-imidazole polyamide can be conveniently synthesized and a peptide (protein) can be easily transferred. According to this method, a pyrrole-imidazole polyamide having a carboxylate group which can be excised from a solid phase carrier at its end, makes it possible to directly transfer various functional groups and can exactly distinguish DNA sequences can be efficiently produced. A method of synthesizing a pyrrole-imidazole polyamide characterized by performing automatic synthesis by the solid phase Fmoc method with the used of a peptide synthesizer; a pyrrole-imidazole polyamide having a carboxyl group at its end obtained by this method; a pyrrole-imidazole polyamide having a DNA alkylation agent transferred into the carboxyl group at the end of the above-described pyrrole-imidazole polyamide; and a sequence-specific DNA alkylation method characterized by using the above compound.

Synthesis of N-methylpyrrole and N-methylimidazole amino acids suitable for solid-phase synthesis

New and higher yielding synthetic routes to N-protected N-methylpyrrole and N-methylimidazole amino acids are introduced to circumvent difficulties associated with established schemes. Key steps in each synthesis include copper-mediated cross-coupling reaction to directly install a carbamate-protected 4-amine in the N-methylpyrrole derivative and effective nitration followed by a one-pot reduction/Boc protection of the amine in the synthesis of the N-Me-imidazole amino acid.

Fmoc solid phase synthesis of polyamides containing pyrrole and imidazole amino acids

Matrix presented Polyamides containing N-methylimidazole (Im) and N-methylpyrrole (Py) amino acids are synthetic ligands that have an affinity and specificity for DNA comparable to those of many naturally occurring DNA binding proteins. A machine-assisted Fmoc solid phase synthesis of polyamides has been optimized to afford high stepwise coupling yields (>99%). Two monomer building blocks, Fmoc-Py acid and Fmoc-Im acid, were prepared in multigram scale. Cleavage by aminolysis followed by HPLC purification affords up to 200 mg quantities of polyamide with purities and yields greater than or equal to those reported using Boc chemistry. A broader set of reaction conditions will increase the number and complexity of minor groove binding polyamides which may be prepared and help ensure compatibility with many commercially available peptide synthesizers.

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.