144790-01-2

Basic information

• Product Name: 2-Azetidinone, 3-(acetyloxy)-4-phenyl-, (3R,4S)-
• CAS NO: 144790-01-2
• Molecular Formula: C11H11NO3
• Molecular Weight: 205.213
• Mol File: 144790-01-2.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: 2-Azetidinone, 3-(acetyloxy)-4-phenyl-, (3R,4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 3-(acetyloxy)-4-phenyl-, (3R,4S)-(144790-01-2)
• EPA Substance Registry System: 2-Azetidinone, 3-(acetyloxy)-4-phenyl-, (3R,4S)-(144790-01-2)

Safety Data

• Hazardous Substances Data: 144790-01-2(Hazardous Substances Data)

Usage

Primary use

Anticonvulsant medication for treating seizures in patients with epilepsy

Mechanism of action

Stabilizes overexcited nerve cells that cause seizures
Alternative to other anticonvulsants
Effective in preventing and controlling seizures in both adults and children
Can also be prescribed for bipolar disorder and neuropathic pain
Available in tablet or suspension form
Dosage varies based on age, condition, and response to the medication
Important to follow prescribed dosage and healthcare professional's instructions

Upstream product

• 104-94-9 4-methoxy-aniline 
• 13831-31-7 Acetoxyacetyl chloride 
• 133066-59-8 (±)-cis-3-acetyloxy-4-phenylazetidin-2-one 
• 186613-02-5 cis-1-p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one 
• 185222-11-1 3-acetyloxy-4-phenyl-2-azetidinone 
• 153463-27-5 (R)-3-[(3R,4S)-1-(4-Methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl]-4-phenyl-oxazolidin-2-one 
• 146924-94-9 (3R,4S)-(+)-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 153545-11-0 (S)-1-(4-Methoxy-phenyl)-4-phenyl-azetidine-2,3-dione 
• 40339-42-2 4-methoxy-N-[(1Z)-phenylmethylene]aniline 
• 206447-89-4 N-(p-methoxyphenyl) (2R,3S)-2,3-dihydroxy-3-phenylpropionamide 
• 206447-91-8 N-(p-methoxyphenyl) (2S,3R)-2-acetoxy-3-bromo-3-phenylpropionamide 
• 76228-15-4 (2E)-N-(4-methoxyphenyl)cinnamamide 
• 208848-58-2 Acetic acid (3R,4S)-1-[(S)-1-(4-methoxy-phenyl)-propyl]-2-oxo-4-phenyl-azetidin-3-yl ester 
• 146924-90-5 (+)-cis-(3R,4S)-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 

Downstream Products

• 132127-34-5 (3R,4S)-3-hydroxy-4-phenylazetidin-2-one 
• 149249-91-2 (3R,4S)-1-benzoyl-4-phenyl-3-(triethylsilyl)oxy-2-azetidinone 
• 149140-54-5 (3R,4S)-3-triethylsilyloxy-4-phenylazetidin-2-one 

Relevant articles and documents

ECD spectrometric methods for detecting the enantioselective enzymatic hydrolysis of racemic 3-acetoxy-4-phenyl-β-lactam

(-)-(3R, 4S)-3-Acetoxy-4-phenylazetidin-2-one ((-)-1) was the key intermediate for preparing optical C-13 side-chain moiety in partial synthesis of docetaxel and paclitaxel. It can be successfully prepared via enantioselective hydrolysis of racemic esters

N-Thiolated β-lactam antibacterials: Effects of the N-organothio substituent on anti-MRSA activity

A study on the structure-activity profiles of N-thiolated β-lactams 1 is reported which demonstrates the importance of the N-organothio moiety on antibacterial activity. Our results indicate that elongation of the N-alkylthio residue beyond two carbons, or extensive branching within the organothio substituent, diminishes antibacterial effects. Of the derivatives we examined, the N-sec-butylthio β-lactam derivative 5g possesses the strongest growth inhibitory activity against methicillin-resistant Staphylococcus aureus strains. Sulfur oxidation state is important, as the N-sulfenyl and N-sulfinyl groups provide for the best antibacterial activity, while lactams bearing the N-sulfonyl or N-sulfonic acid functionalities have much weaker or no anti-MRSA properties. Stereochemistry within the organothio chain does not seem to be a significant factor, although for N-sec-butylthio β-lactams 15a-d, the 3R,4S-lactams 15c, d are more active than the 3S,4R-stereoisomers 15a, b in agar diffusion experiments. The N-methylthio lactams are the most sensitive to the presence of glutathione, followed by N-ethylthio and N-sec-butylthio lactams, which indicates that bioactivity and perhaps bacterial selectivity of the lactams may be related to the amount of organothiols in the bacterial cell. These results support the empirical model for the mechanism of action of the compounds in which the lactam transverses the bacterial membrane to deliver the organothio moiety to its cellular target.

β-lactams, methods for the preparation of taxanes, and sidechain-bearing taxanes

Novel β-lactams finding utility as intermediates in the preparation of sidechain-bearing taxanes such as taxol and taxol derivatives. The present invention also relates to novel methods of coupling β-lactams to form such sidechain-bearing taxanes, and to