anaxirone
anaxirone Basic information
- Product Name:
- anaxirone
- Synonyms:
-
- anaxirone
- 1,2,4-triglycidyl urazol
- 1,2,4-Tris(oxiran-2-ylmethyl)-1,2,4-triazolidine-3,5-dione
- NSC-332488
- Triglycidylurazole
- 1,2,4-Triazolidine-3,5-dione,1,2,4-tris(2-oxiranylmethyl)-
- CAS:
- 77658-97-0
- MF:
- C11H15N3O5
- MW:
- 269.25
- EINECS:
- 278-745-8
- Mol File:
- 77658-97-0.mol
anaxirone Chemical Properties
- Melting point:
- 91°C
- Boiling point:
- 412.4°C (rough estimate)
- Density
- 1.2986 (rough estimate)
- refractive index
- 1.4930 (estimate)
- pka
- -1.72±0.20(Predicted)
- Water Solubility
- 0.2g/L(temperature not stated)
anaxirone Usage And Synthesis
Originator
Anaxirone, Onbio Inc.
Uses
Triglycidylurazole is a drug shown to reduce tumor-induced bone destruction in the rat.
Manufacturing Process
In a 4-liter three-necked flask equipped with a stirrer, thermometer and reflux condenser, 101 g (1 mole) of triazolidine-3,5-dione, 2775 g (30 moles) of epichlorohydrin and 2 ml of triethylamine are heated to 80°C by means of an oil bath. The mixture reacts exothermically so that the oil bath may be removed. After the exothermic reaction has abated, the reaction mixture is stirred at 80°C. The total reaction time is 10 hours. 250 g of 50% sodium hydroxide solution are added dropwise to the solution obtained over a period of 4 hours at from 30 to 40°C in such a way that the water added and the water formed during the reaction is continuously removed by azeotropic distillation at from 30 to 60 Torr using a water separator. To complete the reaction, the reaction mixture is stirred for another hour and the sodium chloride formed is separated by filtration. The sodium chloride is washed twice with 200 g of epichlorohydrin and the combined epichlorohydrin solutions are washed with 200 ml of water. After the organic phase has been dried over sodium sulfate, the solvent is removed by concentration in a rotary evaporator and the residue is dried, ultimately at 80°C/0.2 mbar, to constant weight. 240 g of a light brown viscous oil are obtained. It was found to have an epoxide value of 0.93 and has a chlorine content of 2.75%. The viscous oil crystallizes after standing for from a few hours to days. The practically pure 1,2,4- triglycidyl triazolidine-3,5-dione melting at from 98° to 103°C crystallizes by dissolution in methanol and cooling to 5°C. IR- and NMR-spectra in conjunction with elemental analysis and epoxide determination confirm the assumed structure. Melting point 94-96°C.
Therapeutic Function
Antineoplastic