Azetirelin
Azetirelin Basic information
- Product Name:
- Azetirelin
- Synonyms:
-
- 1-[Nα-[[(S)-4-Oxo-2-azetidinyl]carbonyl]-L-histidyl]-L-prolinamide
- Nα-[(S)-4-Oxo-2-azetidinyl]carbonyl-L-His-L-Pro-NH2
- Nα-[[(S)-4-Oxo-2-azetidinyl]carbonyl]-L-His-L-Pro-NH2
- YM-14673
- Azetirelin
- Nα-[((S)-4-oxo-2-azetidinyl)carbonyl]-L-histidyl-L-prolineamide
- Azetirelin (~85%)
- Azetirelina
- CAS:
- 95729-65-0
- MF:
- C15H20N6O4
- MW:
- 348.36
- Mol File:
- 95729-65-0.mol
Azetirelin Chemical Properties
- Melting point:
- >125°C (dec.)
- Boiling point:
- 997.1±65.0 °C(Predicted)
- Density
- 1.469±0.06 g/cm3(Predicted)
- storage temp.
- -20°C Freezer, Under inert atmosphere
- solubility
- DMSO (Slightly), Methanol (Slightly), Water (Very Slightly, Heated)
- form
- Solid
- pka
- 13.98±0.40(Predicted)
- color
- Off-White
Azetirelin Usage And Synthesis
Originator
Azetirelin,ZYF Pharm Chemical
Uses
Azetirelin is a thyrotropin-releasing hormone (TRH) analogue. It demonstrated neuroprotective activity in rats.
Manufacturing Process
In 13 ml of DMF was dissolved 826.0 mg of L-histidyl-L-prolinamide 2-
hydrobromide and then 2 ml of a DMF solution of 405.0 mg of triethylamine
was added to the solution under ice-cooling. After maintaining 30 min under
ice-cooling, the precipitates thus formed were filtered off to provide L-histidyl-
L-prolinamide.
In 10 ml of DMF was dissolved 230.0 mg of (S)-2-azetidinone-4-carboxylic
acid and then 351.0 mg of N-hydroxy-1,2,3-benzotriazole and 453.0 mg of
dicyclohexylcarbodiimide were added to the solution under ice-cooling. Then,
after stirring the mixture for 15 min, the reaction was maintained for 15 min
at room temperature. The reaction mixture was ice-cooled again and 15 ml of
a DMF solution of foregoing L-histidyl-L-prolinamide was added to the reaction
mixture followed by reaction overnight at 0°C. The precipitates thus formed
were filtered off, the filtrate was concentrated to dryness, the residue was
dissolved in 10 ml of chloroform-methanol (4:1) and subjected to silica gel
column chromatography. The eluates by chloroform-methanol (7:3) were
collected and concentrated to dryness to provide 509.0 mg of crude product.
When the product was subjected to silica gel column chromatography again
and eluted by a mixture of chloroform, methanol, and aqueous ammonia
(40:10:1) to provide 394.0 mg of pure Nepsilon-[(S)-2-azetidinone-4-carbonyl]-
L-histidyl-L-prolinamide, melting point 183°-185°C (crystallization from a
small amount of methanol).
Therapeutic Function
TRH analogue