| Targets |
This chiral β-lactam is a key side chain for the synthesis of docetaxel and paclitaxel. The β-lactam ring can be opened to form the C13 side chain of taxanes. The (3R,4S) stereochemistry is essential for the biological activity of the final drug products. The hydroxyl group provides a handle for further derivatization.
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|---|---|
| ln Vitro |
In vitro, this compound is used as a starting material for synthesizing the C13 side chain of docetaxel and paclitaxel. The β-lactam ring opening reaction is a key step in the synthesis of these anticancer drugs. The compound's role is to enable the production of taxane-based therapeutics.
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| ln Vivo |
In vivo, docetaxel and paclitaxel, synthesized using this side chain, are anticancer drugs that stabilize microtubules and prevent their depolymerization, leading to cell cycle arrest and apoptosis. They are used to treat various cancers including breast, ovarian, and lung cancer.
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| Enzyme Assay |
For synthesis applications, the compound is used as a starting material for the preparation of the C13 side chain of docetaxel. The β-lactam ring is opened using appropriate reagents to form the N-benzoyl-3-phenylisoserine ester side chain. The reaction is carried out in organic solvents with suitable catalysts.
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| Cell Assay |
For cell-based studies, docetaxel and paclitaxel synthesized using this side chain are evaluated in cancer cell lines. Cells are cultured in DMEM or RPMI-1640 with 10% FBS at 37°C in 5% CO₂. Cells are treated with taxanes at 0.1 nM-10 µM for 48-72 hours. Cell viability is assessed using MTT or CellTiter-Glo assays.
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| Animal Protocol |
For in vivo studies, docetaxel and paclitaxel are formulated in suitable vehicles and administered intravenously to tumor-bearing mice at 5-30 mg/kg. Tumor volume is measured every 2-3 days. Pharmacokinetic studies determine compound exposure and half-life. Toxicity is monitored by body weight and clinical observations.
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| ADME/Pharmacokinetics |
(3R,4S)-3-Hydroxy-4-phenylazetidin-2-one has a molecular weight of 163.17 g/mol, a melting point of 187-188°C, a density of 1.3±0.1 g/cm³, and a boiling point of 430.4±45.0°C. It is typically stored as a solid at room temperature with a purity of ≥98% (HPLC). It is soluble in organic solvents.
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| Toxicity/Toxicokinetics |
Acute toxicity data are limited. Standard laboratory safety practices should be followed. The compound may cause skin and eye irritation upon contact. Proper personal protective equipment should be used. Long-term toxicity studies have not been reported for this intermediate.
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| Additional Infomation |
This compound is a chiral β-lactam that serves as a key side chain for the synthesis of docetaxel and paclitaxel. The (3R,4S) stereochemistry is essential for the biological activity of the final drug products. It is a research chemical and is not an FDA-approved drug.
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| Exact Mass |
163.063
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|---|---|
| CAS # |
132127-34-5
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| PubChem CID |
10219589
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
430.4±45.0 °C at 760 mmHg
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| Melting Point |
187-188ºC
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| Flash Point |
214.1±28.7 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.612
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| LogP |
-0.72
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
12
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| Complexity |
187
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| Defined Atom Stereocenter Count |
2
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| InChi Key |
FBZSDKXFQUKDLD-JGVFFNPUSA-N
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| InChi Code |
InChI=1S/C9H9NO2/c11-8-7(10-9(8)12)6-4-2-1-3-5-6/h1-5,7-8,11H,(H,10,12)/t7-,8+/m0/s1
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| Chemical Name |
(3R,4S)-3-hydroxy-4-phenylazetidin-2-one
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Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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