112373-17-8

Basic information

• Product Name: 3-METHOXY-1H-PYRROLE-2-CARBOXYLIC ACID METHYL ESTER
• Synonyms: 3-METHOXY-1H-PYRROLE-2-CARBOXYLIC ACID METHYL ESTER
• CAS NO: 112373-17-8
• Molecular Formula: C₇H₉NO₃
• Molecular Weight: 155.15126
• EINECS: -0
• Mol File: 112373-17-8.mol

Chemical Properties

• Melting Point: 112-114 °C
• Boiling Point: 283.6±20.0 °C(Predicted)
• Appearance: /
• Density: 1.196±0.06 g/cm3(Predicted)
• PKA: 14.65±0.50(Predicted)
• CAS DataBase Reference: 3-METHOXY-1H-PYRROLE-2-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHOXY-1H-PYRROLE-2-CARBOXYLIC ACID METHYL ESTER(112373-17-8)
• EPA Substance Registry System: 3-METHOXY-1H-PYRROLE-2-CARBOXYLIC ACID METHYL ESTER(112373-17-8)

Safety Data

• Hazardous Substances Data: 112373-17-8(Hazardous Substances Data)

Usage

Main Properties

1. Chemical Name: 3-Methoxy-1H-pyrrole-2-carboxylic acid methyl ester
2. Molecular Formula: \textC8\textH9\textNO3
3. Type: Methyl ester
4. Parent Compound: 3-methoxy-1H-pyrrole-2-carboxylic acid
5. Biological Activities: Potential pharmacological and biological activities
6. Applications: Studied for medicinal chemistry and drug discovery

Structure

Heterocyclic compound

Potential Applications

Anti-inflammatory and analgesic properties

Research Interest

Due to its unique structure and functional groups

Potential as a Drug Candidate

Subject to further research and development

Organic Synthesis

Potential applications in organic synthesis

Building Block

Used as a building block for the synthesis of complex organic compounds

This compound presents intriguing possibilities in pharmaceutical research and organic synthesis due to its structure and potential pharmacological activities. Further exploration of its properties and applications could lead to valuable developments in medicine and chemistry.

Upstream product

• 112373-16-7 4,5-diiodo-3-methoxy-2-(methoxycarbonyl)pyrrole 

Downstream Products

• 82-89-3 4-methoxy-5-[(Z)-(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-1H,1'H-2,2'-bipyrrole 
• 112373-38-3 C₁₇H₁₈N₄O₄S 
• 10476-41-2 4-methoxy-2,2'-bipyrrole-5-carboxaldehyde 

Relevant articles and documents

Total Synthesis of Prodigiosin, Prodigiosene, and Desmethoxyprodigiosin: Diels-Adler Reactions of Heterocyclic Azadienes and Development of an Effective Palladium(II)-Promoted 2,2'-Bipyrrole Coupling Procedure

The total synthesis of prodigiosin (1), a red pigment first isolated from Serratia marcescens, possessing the characteristic pyrrolylpyrromethene skeleton of a class of naturally occurring polypyrroles exhibiting antimicrobial and cytotoxic properties, is detailed.The approach is based application of an inverse electron demand Diels-Adler reaction of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate in a 1,2,4,5-tetrazine--->1,2-diazine--->pyrrole strategy for preparation of prodigiosin pyrrole ring B and the subsequent implementation of an effective intramolecular palladium(II)-promoted 2,2'-diaryl coupling for construction of the prodigiosin 2,2'-bipyrrole AB ring system.In situ generated activated ester derivatives of pyrrole-1-carboxylic acid or the use of pyrrole-1-carboxylic acid anhydride proved suitable for the generation of mixed 1,1'-carbonyldipyrrole compounds for use in the palladium(II)-promoted mixed, 2,2'-bipyrrole coupling.Extensions of this approach to the preparation of the naturally occurring parent pyrrolylpyrromethene, prodigiosene (2a), and 2-methyl-3-pentylprodigiosene (2e, desmethoxyprodigiosin) are detailed.A comparison of the in vitro cytotoxic properties of prodigiosin (1), prodigiosene (2a), and 2-methyl-3-pentylprodigiosene (2e) are reported and reveal exceptional cytotoxic potency (3.7*10-4 μg/mL = 3.7*10-10 g/mL) for prodigiosin against 9PS (P388) mouse leukemia which may be attributed to the presence of the prodigiosin C-6 methoxy substituent.

TOTAL SYNTHESIS OF PRODIGIOSIN

The total synthesis of prodigiosin (1), possessing the characteristic pyrrolylpyrromethene skeleton of a class of naturally-occuring polypyrroles, is detailed.The approach is based on the application of an inverse electron demand Diels-Alder reaction of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate in a 1,2,4,5-tetrazine -> 1,2-diazine -> pyrrole strategy for preparation of prodigiosin pyrrole ring B and the subsequent implementation of an intramolecular palladium(II)-promoted 2,2'-diaryl (2,2'-bipyrrole) coupling for construction of the prodigiosin 2,2'-bipyrrole AB ring system.