59194-25-1

Basic information

• Product Name: 1H-Pyrrole, 1-(4-methoxy-2-nitrophenyl)-
• CAS NO: 59194-25-1
• Molecular Formula: C11H10N2O3
• Molecular Weight: 218.212
• Mol File: 59194-25-1.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole, 1-(4-methoxy-2-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole, 1-(4-methoxy-2-nitrophenyl)-(59194-25-1)
• EPA Substance Registry System: 1H-Pyrrole, 1-(4-methoxy-2-nitrophenyl)-(59194-25-1)

Safety Data

• Hazardous Substances Data: 59194-25-1(Hazardous Substances Data)

Usage

Structure

A derivative of pyrrole with a substitution of a 4-methoxy-2-nitrophenyl group at the 1-position

Usage

Commonly used in organic synthesis and medicinal chemistry as a building block for the synthesis of various pharmaceuticals and biologically active molecules

Potential use

Studied for its potential use in the development of new drugs with anti-inflammatory and anti-cancer properties

Research interest

Unique structural features make it an interesting target for further research in the fields of organic chemistry and drug discovery

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 96-96-8 4-methoxy-2-nitroaniline 
• 109-97-7 pyrrole 
• 5344-78-5 4-bromo-3-nitroanizole 
• 61324-93-4 1-fluoro-nitro-4-methoxybenzene 

Downstream Products

• 59194-26-2 2–(1H–pyrrol–1–yl)–5–methoxyaniline 
• 1259378-47-6 C₂₄H₂₂N₄O₂ 
• 1184997-31-6 7'-methoxy-1-[4-(2,2,2-trifluoroethoxy)benzoyl]spiro[piperidine-4,4'(5'H)-pyrrolo[1,2-a]quinoxaline] 
• 1259378-43-2 C₂₅H₂₈N₄O₂ 
• 1259380-66-9 1-[3-(dimethylamino)-4-methoxybenzoyl]-7'-methoxyspiro[piperidine-4,4'(5'H)-pyrrolo[1,2-a]quinoxaline] 
• 958707-54-5 7'-methoxy-5'H-spiro[piperidine-4,4'-pyrrolo[1,2-a]quinoxaline] 
• 1189967-05-2 C₂₄H₂₂N₄O₂ 

Relevant articles and documents

Simple and green synthesis of benzimidazoles and pyrrolo[1,2-: A] quinoxalines via Mamedov heterocycle rearrangement

A method for the synthesis of coupling compounds of benzimidazoles and pyrrolo[1,2-a]quinoxalines via Mamedov Heterocycle Rearrangement is reported here. This method was conducted at room temperature and only solvent (HOAc) was required. A series of 4-(1H-benzo[d]imidazol-2-yl)pyrrolo[1,2-a]quinoxaline derivatives were obtained in moderate to good yields.

Pyrrolo[1,2-a]quinoxalines: Insulin Mimetics that Exhibit Potent and Selective Inhibition against Protein Tyrosine Phosphatase 1B

PTP1B dephosphorylates insulin receptor and substrates to modulate glucose metabolism. This enzyme is a validated therapeutic target for type 2 diabetes, but no current drug candidates have completed clinical trials. Pyrrolo[1,2-a]quinoxalines substituted at positions C1–C4 and/or C7–C8 were found to be nontoxic to cells and good inhibitors in the low- to sub-micromolar range, with the 4-benzyl derivative being the most potent inhibitor (0.24 μm). Some analogues bearing chlorine atoms at C7 and/or C8 kept potency and showed good selectivity compared to TCPTP (selectivity index '40). The most potent inhibitors behaved as insulin mimetics by increasing glucose uptake. The 4-benzyl derivative inhibited insulin receptor substrate 1 and AKT phosphorylation. Molecular docking and molecular dynamics simulations supported a putative binding mode for these compounds to the allosteric α3/α6/α7 pocket, but inconsistent results in enzyme inhibition kinetics were obtained due to the high tendency of these inhibitors to form stable aggregates. Computational calculations supported the druggability of inhibitors.

A new pathway to pyrrolo[1,2-a]quinoxalines via solvent-free one-pot strategy utilizing FeMoSe nanosheets as efficient recyclable synergistic catalyst

FeMoSe nanocatalyst was synthesized using solvothermal approach from readily available precursors, namely Mo(CO)6, FeSO4 and Se, and characterized by spectroscopic and microscopic analyses. The FeMoSe material offered high catalytic