144790-01-2

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

• 133066-59-8 (±)-cis-3-acetyloxy-4-phenylazetidin-2-one 
• 146924-90-5 (+)-cis-(3R,4S)-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 
• 208848-58-2 Acetic acid (3R,4S)-1-[(S)-1-(4-methoxy-phenyl)-propyl]-2-oxo-4-phenyl-azetidin-3-yl ester 
• 153545-11-0 (S)-1-(4-Methoxy-phenyl)-4-phenyl-azetidine-2,3-dione 
• 13831-31-7 Acetoxyacetyl chloride 
• 104-94-9 4-methoxy-aniline 
• 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 
• 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 

Downstream Products

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

Relevant academic research and scientific papers

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

New enzymatic two-step cascade reaction for the preparation of a key intermediate for the taxol side-chain

Enzymatic strategies are reported for the synthesis of (2R, 3S)-3-amino-2-hydroxy-3-phenylpropionic acid (ee > 98%), a key intermediate of the side-chain of Taxolby enzymatic hydrolysis in organic media. The new enzymatic cascade reaction, which took place through Candida antarctica lipase B-catalysed deacylation followed by lactam ring-opening of racemic cis-3-acetoxy-4-phenylazetidin-2-one with H2O in iPr2O at: 60 °C, resulted in two different enantiopure products (ee ≥ 98%), one of them being the desired key intermediate for the side-chain of Taxol.

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 novel sidechain-bearing taxanes.

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

A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor

A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one, an important precursor for the paclitaxel side chain, has been developed using intramolecular cyclization of N-(p-methoxyphenyl) (2S,3R)-2-acetoxy-3-bromo- 3-phenylpropionamide which can be easily obtained by catalytic asymmetric dihydroxylation of N-(p-methoxyphenyl)-trans-cinnamide, followed by bromoacetylation.

A convenient synthesis of the paclitaxel side-chain via a diastereoselective Staudinger reaction

The N-benzylidene dexivative of (S)-(-)-1-(p-mathoxyphenyl)propyl-1- amine, obtained by a new resolution procedure, exhibits moderate selectivity in the reaction with 2-acetoxyketene; the (S)-(-)-1-(p-methoxyphenyl)propyl group can be oxidatively cleaved from the resultant β-lactam, an important precursor for taxane semi-synthesis.

Biocatalytic synthesis of some chiral pharmaceutical intermediates by lipases

Chiral intermediates were prepared by biocatalytic processes for the chemical synthesis of three pharmaceutical drug candidates. These include (i) the synthesis of [(3R-cis)-3-(acetyloxy)-4-phenyl-2-azetidinone 2 for the semi-synthesis of paclitaxel (taxol) 5, an anticancer compound; (ii) synthesis of chiral (exo,exo)-7-oxabicyclo [2.2.1] heptane-2,3-dimenthanol monoacetate ester 9 for the chemoenzymatic preparation of a thromboxane A2 antagonist; (iii) the enzymatic synthesis of S-(-) 3-benzylthio-2-methylpropanoic acid, a key chiral intermediate for the synthesis of antihypertensive drugs captopril 10 or zofenopril 13.

N-substituted 2-azetidinones

Novel cis compound having the formula: STR1 wherein R1 is alkyl, haloalkyl, cycloalkyl, aryl or a carbohydrate derivative; X is O, N, S, C(O)O or a direct bond; and R2 is aryl, substituted aryl or heteroaryl are useful in the synthes

6,7-epoxy paclitaxels

The present invention provides paclitaxel derivatives of formula I STR1 in which R1 is --CORz, in which Rz is RRo N--, RHN--, RO-- or R; R2 is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, or a radical of the formula --W--Rx in which W is a bond, C2-6 alkenediyl, or --(CH2)t --, in which t is one to six; and Rx is naphthyl, phenyl, or heteroaryl, and furthermore Rx can be optionally substituted with one to three same or different C1-6 alkyl, C1-6 alkoxy, halogen or --CF3 groups; R and Ro are independently C1-6 alkyl, C2-6 alkenyl, C3-6 cycloalkyl, C2-6 alkynyl, or phenyl, optionally substituted with one to three same or different C1-6 alkyl, C1-6 alkoxy, halogen or --CF3 groups. Also provided by this invention are pharmaceutical formulations (compositions) and a method of treating mammalian tumors with a compound of formula I.