126092-96-4

Usage

Uses

Used in Pharmaceutical Research and Development:
1H-Pyrrole-2-carboxylic acid, 4-[[(1,1-diMethylethoxy)carbonyl]aMino]-1-Methyl-, Methyl ester is used as a key intermediate in the synthesis of various pharmaceutical compounds for its potential to form stable and bioactive molecules. The presence of the pyrrole ring and the protected amino group allows for the creation of diverse drug candidates with specific therapeutic properties.
Used in Chemical Synthesis:
In the chemical synthesis industry, 1H-Pyrrole-2-carboxylic acid, 4-[[(1,1-diMethylethoxy)carbonyl]aMino]-1-Methyl-, Methyl ester serves as a versatile building block for the creation of complex organic molecules. Its unique structure allows chemists to explore various synthetic pathways, leading to the development of novel compounds with potential applications in different fields.
Used in Biochemical Research:
1H-Pyrrole-2-carboxylic acid, 4-[[(1,1-diMethylethoxy)carbonyl]aMino]-1-Methyl-, Methyl ester is utilized in biochemical research to study the interactions of pyrrole-containing compounds with biological systems. 1H-Pyrrole-2-carboxylic acid, 4-[[(1,1-diMethylethoxy)carbonyl]aMino]-1-Methyl-, Methyl ester's structure enables researchers to investigate its binding properties, enzymatic activity, and potential as a modulator of biological processes.
Used in Drug Design:
In the field of drug design, 1H-Pyrrole-2-carboxylic acid, 4-[[(1,1-diMethylethoxy)carbonyl]aMino]-1-Methyl-, Methyl ester is employed as a template for the development of new therapeutic agents. Its unique structural features, including the pyrrole ring and the protected amino group, offer opportunities for the design of drugs with improved pharmacokinetic and pharmacodynamic profiles.
Used in Medicinal Chemistry:
1H-Pyrrole-2-carboxylic acid, 4-[[(1,1-diMethylethoxy)carbonyl]aMino]-1-Methyl-, Methyl ester is used in medicinal chemistry as a starting material for the synthesis of bioactive molecules with potential therapeutic applications. 1H-Pyrrole-2-carboxylic acid, 4-[[(1,1-diMethylethoxy)carbonyl]aMino]-1-Methyl-, Methyl ester's structural attributes make it a valuable component in the development of new drugs targeting various diseases and conditions.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 72083-62-6 methyl 4-amino-1-methyl-1H-pyrrole-2-carboxylate 
• 180258-45-1 methyl 4-amino-1-methyl-pyrrole-2-carboxylate hydrochloride 
• 13138-76-6 1-methyl-4-nitropyrrole-2-carboxylic acid methyl ester 
• 4248-19-5 tert-butyl carbazate 
• 40740-42-9 4-iodo-1-methyl-pyrrole-2-carboxylic acid methyl ester 
• 126093-10-5 methyl N-methyl-4-aminopyrrole-2-carboxylate trifluoroacetate 
• 500903-64-0 (5-chlorocarbonyl-1-methyl-1H-pyrrol-3-yl)-carbamic acid tert-butyl ester 
• 37619-24-2 methyl N-methylpyrrole-2-carboxylate 
• 6973-60-0 1-Methyl-2-pyrrolecarboxylic acid 
• 184643-69-4 1-(4-bromo-1-methyl-1H-pyrrol-2-yl)-2,2,2-trichloroethan-1-one 
• 21898-65-7 1-methyl-2-trichloroacetyl-1H-pyrrole 
• 96-54-8 N-Methylpyrrole 
• 1196-90-3 4-bromo-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester 

Downstream Products

• 72083-62-6 methyl 4-amino-1-methyl-1H-pyrrole-2-carboxylate 
• 251999-70-9 (E)-p-nitrophenyl 1-methyl-4-[(tert-butoxycarbonyl)amino]-2-pyrrolylacrylate 
• 126093-05-8 (5-{5-[5-({[4-(Acridin-9-ylamino)-phenylcarbamoyl]-methyl}-carbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl]-1-methyl-1H-pyrrol-3-ylcarbamoyl}-1-methyl-1H-pyrrol-3-yl)-carbamic acid tert-butyl ester 
• 126093-04-7 4-(9-acridinylamino)-N-<4-<<<4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrol-2-yl>carbonyl>amino>-1-methyl-pyrrol-2-carbonyl>glycylaniline 
• 126093-03-6 4-(9-acridinylamino)-N-<4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrol-2-carbonyl>glycylaniline 
• 126093-02-5 benzyl 4-(formylamino)-1-methyl-pyrrole-2-carboxylate 
• 77716-20-2 Benzyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate 
• 77716-15-5 benzyl 4-<<<4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrol-2-yl>carbonyl>amino>-1-methyl-pyrrole-2-carboxylate 
• 77716-13-3 benzyl 4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrole-2-carboxylate 
• 77716-19-9 Benzyl 4-<<(4-Amino-1-methylpyrrol-2-yl)carbonyl>amino>-1-methylpyrrole-2-carboxylate 
• 77716-14-4 Benzyl 4-Amino-1-methylpyrrole-2-carboxylate 
• 77716-16-6 4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylic acid benzotriazol-1yl ester 
• 126092-97-5 methyl 4-<<<4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrol-2-yl>carbonyl>amino>-1-methyl-pyrrole-2-carboxylate 
• 126092-98-6 4-<<<4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrol-2-yl>carbonyl>amino>-1-methyl-pyrrole-2-carboxylic acid 

Relevant academic research and scientific papers

Guanine-Containing DNA Minor-Groove binders

Solid-phase procedures have been used to prepare six di-pyrrole-containing DNA ligands that combine (guanin-9-yl)-acetyl, (guanin-7-yl)acetyl or acetyl moieties at the N-terminal end and two lysines or a (dimethylamino)propyl group at the C terminus. Inspection of their DNA-stabilizing properties by UV-monitored thermal denaturation experiments showed that the ligand incorporating the (guanin-9-yl)acetyl group and the (dimethylamino)propyl tail had the highest duplex-stabilizing effects. Wiley-VCH Verlag GmbH & Co, KGaA.

Synthesis of pyrrole-imidazole polyamide oligomers based on a copper-catalyzed cross-coupling strategy

Pyrrole-imidazole (Py-Im) polyamides are useful tools for chemical biology and medicinal chemistry studies due to their unique binding properties to the minor groove of DNA. We developed a novel method of synthesizing Py-Im polyamide oligomers based on a Cu-catalyzed cross-coupling strategy. All four patterns of dimer fragments could be synthesized using a Cu-catalyzed Ullmann-type cross-coupling with easily prepared monomer units. Moreover, we demonstrated that pyrrole dimer, trimer, and tetramer building blocks for Py-Im polyamide synthesis were accessible by combining site selective iodination of the pyrrole/pyrrole coupling adduct.

METHOD FOR PRODUCING NITROGEN-CONTAINING AROMATIC AMIDE, METHOD FOR PRODUCING PYRROLE-IMIDAZOLE POLYAMIDE, AND COMPOUND

To provide a method for producing a nitrogen-containing aromatic amide that is capable of using a monomer unit obtained under milder reaction condition and uses catalytic amide bond formation, and a method for producing a pyrrole-imidazole polyamide. [1] A method for producing a nitrogen-containing aromatic amide, including reacting a compound 1 represented by the general formula (1) and a compound 2 represented by the general formula (2) in the presence of a transition metal catalyst and a base, so as to provide a compound 3 represented by the general formula (3). [2] A method for producing a pyrrole-imidazole polyamide, including using the compound 3 obtained by the production method according to the item [1]. [3] A compound represented by the general formula (2aa), the general formula (2ab), the general formula (2ac), or the general formula (2ad).

Synthesis of distamycin a polyamides targeting G-quadruplex DNA

A number of amide-linked oligopyrroles based on distamycin molecules have been synthesized by solid-state methods, and their interactions with a human intramolecular G-quadruplex have been measured by a melting procedure. Several of these molecules show an enhanced ratio of quadruplex vs. duplex DNA binding compared to distamycin itself, including one with a 2,5-disubstituted pyrrole group. Quadruplex affinity increases with the number of pyrrole groups, and it is suggested that this is consistent with a mixed groove/G-quartet stacking binding mode. The Royal Society of Chemistry 2006.

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.

Alpha- haloenamine reagents

The present invention describes immobilized haloenamine reagents, immobilized tertiary amides, methods for their preparation, and methods of use.

Aromatic and heteroaromatic acid halides for synthesizing polyamides

The present invention is directed to protected amino acid halide monomers and oligomers, and to their use in the efficient sythesis of polyamides. The present invention is further directed to the use of α-haloenamine reagents, which may optionally be immobilized, for the preparation of the amino acid halides.

Solid phase synthesis of polyamides containing imidazole and pyrrole amino acids

The solid phase synthesis of sequence specific DNA binding polyamides containing N-methylimidazole (Im) and N-methylpyrrole (Py) amino acids is described. Two monomer building blocks, Boc-Py-OBt ester and Boc-Im acid, are prepared on a 50 g scale without column chromatography. Using commercially available Boc-β-alanine-Pam resin, cycling protocols were optimized to afford high stepwise coupling yields (>99%). Deprotection by aminolysis affords up to 100 mg quantities of polyamide. Solid phase methodology increases both the number and complexity of minor groove binding polyamides which can be synthesized and analyzed with regard to DNA binding affinity and sequence specificity. The solid phase synthesis of a representative eight-residue polyamide is reported.

Design, synthesis, DNA binding, and biological activity of a series of DNA minor-groove-binding intercalating drugs

A group of pseudopeptides, molecular combination of the natural antitumor agents distamycin or netropsin and the anilinoacridine chromophore (which is related to the synthetic antileukemic drug amsacrine) has been synthesized. Their DNA binding properties were determined and discussed in terms of their structural differences and in relation to their observed base-dependent binding. Binding data are consistent with a model in which the acridine nucleus occupies an intercalation site and the netropsin or distamycin residue resides in the DNA minor groove. Cytostatic and cytotoxic activities against a murine cell line are reported, as well as significant differences in the inhibition of DNA synthesis.