24863-94-3

Basic information

• Product Name: [(1R,2R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)prop yl] acetate
• Synonyms: [(1R,2R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)prop yl] acetate
• CAS NO: 24863-94-3
• Molecular Formula: C13H14Cl2N2O6
• Molecular Weight: 365.1661
• Mol File: 24863-94-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 569.5 °C at 760 mmHg
• Flash Point: 298.2 °C
• Appearance: /
• Density: 1.473 g/cm³
• Vapor Pressure: 8.32E-14mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: [(1R,2R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)prop yl] acetate(CAS DataBase Reference)
• NIST Chemistry Reference: [(1R,2R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)prop yl] acetate(24863-94-3)
• EPA Substance Registry System: [(1R,2R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)prop yl] acetate(24863-94-3)

Safety Data

• Hazardous Substances Data: 24863-94-3(Hazardous Substances Data)

Usage

Description

[(1R,2R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl] acetate is a synthetic compound derived from acetylcholine, a neurotransmitter crucial for nerve signal transmission. [(1R,2R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)prop yl] acetate is designed to mimic acetylcholine's structure and function, featuring a phenyl group, a dichloroacetyl group, an acetate group, and a nitro group, all of which contribute to its biological activity. Its potential applications lie in the treatment of nerve-related disorders, and further research is required to explore its pharmacological properties and therapeutic uses fully.

Uses

Used in Pharmaceutical Industry:
[(1R,2R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl] acetate is used as a potential therapeutic agent for treating nerve-related disorders such as Alzheimer's disease and myasthenia gravis. Its structural similarity to acetylcholine allows it to potentially modulate the activity of acetylcholine receptors, which are often implicated in these conditions.
Used in Drug Development:
In the field of drug development, [(1R,2R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl] acetate serves as a promising lead compound for the creation of new drugs with improved potency and selectivity for acetylcholine receptors. The presence of the nitro group may offer additional avenues for chemical modification and optimization to enhance the compound's pharmacological properties.
Used in Neuroscientific Research:
[(1R,2R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)prop yl] acetate is also utilized in neuroscientific research as a tool to study the role of acetylcholine in various neurological processes and disorders. Understanding its interaction with acetylcholine receptors can provide insights into the development of novel therapeutic strategies for nerve-related conditions.

InChI:InChI=1/C13H14Cl2N2O6/c1-7(19)23-11(10(6-18)16-13(20)12(14)15)8-2-4-9(5-3-8)17(21)22/h2-5,10-12,18H,6H2,1H3,(H,16,20)/t10-,11-/m1/s1

Upstream product

• 56-75-7 chloramphenicol 
• 108-24-7 acetic anhydride 
• 72-89-9 acetylcoenzyme A 
• 864529-25-9 chloramphenicol 
• 10318-17-9 (1R,2R)-3-(acetyloxy)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)propyl acetate 
• 864529-27-1 (1R,2R)-3-((tert-butyldimethylsilyl)oxy)-2-(2,2-dichloroacetamido)-1-(4-nitrophenyl)propyl acetate 

Downstream Products

• 10318-17-9 (1R,2R)-3-(acetyloxy)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)propyl acetate 

Relevant articles and documents

Chloramphenicol Derivatives with Antibacterial Activity Identified by Functional Metagenomics

A functional metagenomic approach identified novel and diverse soil-derived DNAs encoding inhibitors to methicillin-resistant Staphylococcus aureus (MRSA). A metagenomic DNA soil library containing 19 200 recombinant Escherichia coli BAC clones with 100 Kb average insert size was screened for antibiotic activity. Twenty-seven clones inhibited MRSA, seven of which were found by LC-MS to possess modified chloramphenicol (Cm) derivatives, including three new compounds whose structures were established as 1-acetyl-3-propanoylchloramphenicol, 1-acetyl-3-butanoylchloramphenicol, and 3-butanoyl-1-propanoylchloramphenicol. Cm was used as the selectable antibiotic for cloning, suggesting that heterologously expressed enzymes resulted in derivatization of Cm into new chemical entities with biological activity. An esterase was found to be responsible for the enzymatic regeneration of Cm, and the gene trfA responsible for plasmid copy induction was found to be responsible for inducing antibacterial activity in some clones. Six additional acylchloramphenicols were synthesized for structure and antibacterial activity relationship studies, with 1-p-nitrobenzoylchloramphenicol the most active against Mycobacterium intracellulare and Mycobacterium tuberculosis, with MICs of 12.5 and 50.0 μg/mL, respectively.

Synthesis and antimicrobial activity of chloramphenicol-polyamine conjugates

Abstract A series of chloramphenicol (CAM) amides with polyamines (PAs), suitable for structure-activity relationship studies, were synthesized either by direct attachment of the PA chain on the 2-aminopropane-1,3-diol backbone of CAM, previously oxidized selectively at its primary hydroxyl group, or from chloramphenicol base (CLB) through acylation with succinic or phthalic anhydride and finally coupling with a PA. Conjugates 4 and 5, in which the CLB moiety was attached on N4 and N1 positions, respectively, of the N8,N8-dibenzylated spermidine through the succinate linker, were the most potent antibacterial agents. Both conjugates were internalized into Escherichia coli cells by using the spermidine-preferential uptake system and caused decrease in protein and polyamine content of the cells. Noteworthy, conjugate 4 displayed comparable activity to CAM in MRSA or wild-type strains of Staphylococcus aureus and Escherichia coli, but superior activity in E. coli strains possessing ribosomal mutations or expressing the CAM acetyltransferase (cat) gene. Lead compounds, and in particular conjugate 4, have been therefore discovered during the course of the present work with clinical potential.

Isolation of 3' -O-acetylchloramphenicol: a possible intermediate in chloramphenicol biosynthesis.

3' -O-acetylchloramphenicol, commonly formed from chloramphenicol by resistant bacteria, has been isolated from the antibiotic-producing organism. Biosynthetic experiments suggest that it is a protected intermediate in chloramphenicol biosynthesis, implicating acetylation as a self-resistance mechanism in the producing organism.