5264-35-7

Basic information

• Product Name: 5-METHOXY-3,4-DIHYDRO-2H-PYRROLE
• Synonyms: 2-METHOXY-1-PYRROLINE;AKOS BBS-00007016;5-METHOXY-3,4-DIHYDRO-2H-PYRROLE;2-methoxypyrrole;4,5-Dihydro-2-methoxy-3H-pyrrole;2H-Pyrrole, 3,4-dihydro-5-methoxy-;2-methoxy-4,5-dihydro-3H-pyrrole;c-C4H6N(2-OCH3)
• CAS NO: 5264-35-7
• Molecular Formula: C₅H₉NO
• Molecular Weight: 99.13
• Mol File: 5264-35-7.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 120.2°Cat760mmHg
• Flash Point: 26.5°C
• Appearance: /
• Density: 1.05g/cm³
• Vapor Pressure: 18.5mmHg at 25°C
• Refractive Index: 1.49
• Storage Temp.: 2-8°C
• PKA: 6.29±0.20(Predicted)
• CAS DataBase Reference: 5-METHOXY-3,4-DIHYDRO-2H-PYRROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-3,4-DIHYDRO-2H-PYRROLE(5264-35-7)
• EPA Substance Registry System: 5-METHOXY-3,4-DIHYDRO-2H-PYRROLE(5264-35-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5264-35-7(Hazardous Substances Data)

Usage

Uses

2-Methoxy-1-pyrroline acts as a reagent in the design and preparation of dihydroindolones and dihydroindolizinones as orally available MEK inhibitors with potent in vivo antitumor efficacy. Synthesis and anti-HSV activity of methylenedioxy mappicine ketone analogs against herpes viruses.

InChI:InChI=1/C5H9NO/c1-7-5-3-2-4-6-5/h2-4H2,1H3

Upstream product

• 616-45-5 2-pyrrolidinon 
• 77-78-1 dimethyl sulfate 
• 123-75-1 pyrrolidine 
• 96-42-4 pyrrolidin-3-one 
• 584-08-7 potassium carbonate 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 71-43-2 benzene 

Downstream Products

• 103861-77-4 2-(3-methoxyphenyl)pyrrolidine 
• 62686-84-4 3-(pyrrolidin-2-ylidene)pentane-2,4-dione 
• 43003-15-2 N-(2-phenyl-2-oxoethyl)-2-pyrrolidinone 
• 916518-31-5 2-phenyl-1-(3,4-dihydro-2H-pyrrol-5-yl)pyrrolidine 
• 832753-24-9 1-[2-(4-chlorophenyl)-2-oxo-ethyl]pyrrolidin-2-one 
• 832753-10-3 1-[2-(4-bromophenyl)-2-oxo-ethyl]-pyrrolidin-2-one 
• 932-17-2 N-acetylpyrrolidinone 
• 10019-95-1 N-tosylpyrrolidinone 
• 88000-68-4 1-benzenesulfonyl-pyrrolidin-2-one 
• 51599-72-5 1-Methylsulfonyl-2-pyrrolidinone 
• 108140-16-5 (E)-ethyl 3-oxo-3-phenyl-2-(pyrrolidin-2-ylidene)-propanoate 
• 1164519-53-2 3-oxo-3-phenyl-2-pyrrolidin-2-ylidene-propionitrile 

Relevant articles and documents

-

-

γ-Lactam-Based Antifungal Compounds against the Wheat Pathogen Zymoseptoria tritici

As new environmentally friendly and effective antifungal agents are deeply needed, efficient ecofriendly strategies were designed to access two series of compounds inspired from natural γ-lactams. Designed compounds were fully characterized and evaluated as antifungal candidates against Zymoseptoria tritici, the main pathogen on wheat crops. The targeted derivatives were prepared from natural resources using green solvents, simple procedures, and limited purification steps. These bio-inspired compounds revealed as good candidates for further development of efficient crop protection products. Indeed, the HIT compounds exhibited IC50 around 1 μg/mL and were more active than the references tebuconazole and bixafen towards some multidrug-resistant strains. Two dozen of derivatives have been obtained for each series and allowed to establish early structure-activity relationships useful for the development of next generation of γ-lactam derivatives with improved efficacy.

Discovery of AZD4573, a Potent and Selective Inhibitor of CDK9 That Enables Short Duration of Target Engagement for the Treatment of Hematological Malignancies

A CDK9 inhibitor having short target engagement would enable a reduction of Mcl-1 activity, resulting in apoptosis in cancer cells dependent on Mcl-1 for survival. We report the optimization of a series of amidopyridines (from compound 2), focusing on properties suitable for achieving short target engagement after intravenous administration. By increasing potency and human metabolic clearance, we identified compound 24, a potent and selective CDK9 inhibitor with suitable predicted human pharmacokinetic properties to deliver transient inhibition of CDK9. Furthermore, the solubility of 24 was considered adequate to allow i.v. formulation at the anticipated effective dose. Short-term treatment with compound 24 led to a rapid dose- and time-dependent decrease of pSer2-RNAP2 and Mcl-1, resulting in cell apoptosis in multiple hematological cancer cell lines. Intermittent dosing of compound 24 demonstrated efficacy in xenograft models derived from multiple hematological tumors. Compound 24 is currently in clinical trials for the treatment of hematological malignancies.