860035-10-5

Basic information

• Product Name: Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester
• Synonyms: Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester;1-((2,5-dioxopyrrolidin-1-yloxy)carbonyloxy)ethyl isobutyrate
• CAS NO: 860035-10-5
• Molecular Formula: C₁₁H₁₅NO₇
• Molecular Weight: 273.2393
• EINECS: -0
• Mol File: 860035-10-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 347.6±44.0 °C(Predicted)
• Appearance: /
• Density: 1.32±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester(860035-10-5)
• EPA Substance Registry System: Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester(860035-10-5)

Safety Data

• Hazardous Substances Data: 860035-10-5(Hazardous Substances Data)

Usage

General Description

Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester, also known as ethyl 2-methylpropanoate, is a chemical compound commonly used as a flavoring agent and in the production of fragrances. It is a colorless liquid with a fruity odor, and is often found in various fruits and alcoholic beverages. Propanoic acid, 2-Methyl-, 1-[[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]oxy]ethyl ester is also used as a solvent in the manufacturing of pharmaceuticals and food products. Additionally, it is used in the production of plasticizers and as an intermediate in the synthesis of other organic compounds. Due to its potential hazardous properties, it is important to handle and store this chemical with care, following appropriate safety procedures.

Upstream product

• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 860035-07-0 O-(1-isobutanoyloxyethyl) S-methyl thiocarbonate 
• 1207383-11-6 1-((4-(methylsulfonyl)phenoxy)carbonyloxy)ethyl isobutyrate 
• 860035-08-1 O-(1-isobutanoyloxyethyl) S-tert-butyl thiocarbonate 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 

Downstream Products

• 918448-02-9 trans-4-{[1-(2-methylpropanoyloxy)ethoxycarbonyl]-aminomethyl}-cyclohexanecarboxylic acid 
• 1206514-65-9 2-[(1-acetyl-4-{hydroxy-[1-(1-isobutyryloxy-ethoxycarbonylamino)ethyl]phosphinoylmethyl}piperidine-4-carbonyl)amino]-ropionic acid 
• 1206514-64-8 2-[(1-{hydroxy-[1-(1-isobutyryloxy-ethoxycarbonylamino)ethyl]phosphinoylmethyl}cyclopentanecarbonyl)amino]propionic acid 
• 1206514-61-5 2-(3-biphenyl-4-yl-2-{hydroxy-[(1-isobutyryloxy-ethoxycarbonylamino)thiophen-3-yl-methyl]phosphinoylmethyl}propionylamino)propionic acid 
• 1206514-59-1 2-[2-{hydroxy-[(1-isobutyryloxy-ethoxycarbonylamino)phenyl-methyl]phosphinoylmethyl}-3-(4-thiophen-3-yl-phenyl)propionylamino]propionic acid 
• 1131570-15-4 [N-(2-hydroxy-tert-butyl)carbamoyloxy]ethyl 2-methylpropanoate 
• 1057258-24-8 3-{[1-isobutanoyloxyethoxy]carbonylamino}propyl phosphonous acid 

Relevant articles and documents

Synthesis, bioconversion, pharmacokinetic and pharmacodynamic evaluation of N-isopropyl-oxy-carbonyloxymethyl prodrugs of CZh-226, a potent and selective PAK4 inhibitor

We have previously disclosed compound 3 (CZh-226), a potent and selective PAK4 inhibitor, but its development was delayed due to poor oral pharmacokinetics. In an attempt to improve this issue, we synthesised a series of prodrugs by masking its terminal nitrogen of the piperazine moiety. Most synthesised prodrugs of 3 have low or no inhibition of PAK4 activity. The stability of synthetic prodrugs was evaluated in PBS, SGF, SIF, rat plasma and liver S9 fraction. Of these, prodrug 19 was not only stable under both acidic and neutral conditions but also could be quickly converted to parent drug 3 in rat plasma and liver S9 fraction. Such effective conversion into parent drug 3 was observed in rats, providing higher exposure of 3 compared to its direct administration. When given via oral route at daily doses of 25 and 50 mg/kg, the prodrug 19 was effective and well tolerated in mouse model of HCT-116 and B16F10.

COMPOUNDS FOR TREATMENT OF NEURODEGENERATIVE DISEASES

Novel compounds of formula (II) are disclosed. Compounds of formula (II) comprise ornithine derivatives or compounds that can metabolize under physiological conditions to ornithine. The pH and plasma stability of compounds of formula (II) is also described. Also disclosed are methods for the treatment of neurodegenerative diseases such as Alzheimer's Disease using compounds of formula (II).

METHODS OF SYNTHESIZING N-HYDROXYSUCCINIMIDYL CARBONATES

The present disclosure relates to methods of synthesizing N-hydroxysuccinimidyl-carbonate intermediates from the corresponding sulfones useful in the preparation of 1-(acyloxy)-alkyl carbamate prodrugs.