| Identification | Back Directory | [Name]
Azetirelin | [CAS]
95729-65-0 | [Synonyms]
YM-14673
Azetirelin
Azetirelina
Azetirelinum
Azetirelin (~85%)
Nα-[(S)-4-Oxo-2-azetidinyl]carbonyl-L-His-L-Pro-NH2
Nα-[[(S)-4-Oxo-2-azetidinyl]carbonyl]-L-His-L-Pro-NH2
L-Prolinamide, (2S)-4-oxo-2-azetidinecarbonyl-L-histidyl-
Nα-[((S)-4-oxo-2-azetidinyl)carbonyl]-L-histidyl-L-prolineamide
1-[Nα-[[(S)-4-Oxo-2-azetidinyl]carbonyl]-L-histidyl]-L-prolinamide | [Molecular Formula]
C15H20N6O4 | [MDL Number]
MFCD00867196 | [MOL File]
95729-65-0.mol | [Molecular Weight]
348.36 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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