(3S-trans)-Hexahydro-3-isobutylpyrrolo[1,2-a]pyrazin-1,4-dion
Cyclo(proline-leucine) · Cyclo(Pro-Leu) · gancidinw · c(Leu-Pro) · Maculosin 6 · Cyclo(-Leu-Pro) · cyclo-l-leu-l-pro · Cyclo(L-Pro-D-Leu)
![Molekülstruktur von (3S-trans)-Hexahydro-3-isobutylpyrrolo[1,2-a]pyrazin-1,4-dion](/img/chemical/7074739.png)
Identifikatoren & physikalische Daten
| CAS No. | 2873-36-1 |
|---|---|
| Summenformel | C11H18N2O2 |
| Durchschnittliche Molmasse | 210,277 g/mol |
| Monoisotopische Masse | 210,13682782 g/mol |
| SMILES | CC(C)C[C@@H]1NC(=O)[C@@H]2CCCN2C1=O |
| InChIKey | SZJNCZMRZAUNQT-IUCAKERBSA-N |
| PubChem CID | 7074739 |
| ChEMBL | CHEMBL508326 |
| ChEBI | CHEBI:133094 |
| EC No. | 220-710-6 |
| DTXSID | DTXSID80951384 |
| Lokaler Name | (3S-trans)-Hexahydro-3-isobutylpyrrolo[1,2-a]pyrazin-1,4-dion |
Chemische & physikalische Eigenschaften
| Schmelzpunkt | 163-165℃ |
|---|---|
| Siedepunkt | 427.6±34.0 °C(Predicted) |
| Dichte | 1.14 |
| Lagerbedingungen | Inert atmosphere,2-8°C |
| Löslichkeit | Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly) |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 13.27±0.40(Predicted) |
| Farbe | White to Off-White |
Sicherheit & Vorschriften
| Toxizität | mouse,LD50,intravenous,80mg/kg (80mg/kg),"Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 2, Pg. 1354, 1978. |
|---|
Anwendungen & Verwendung
Beschreibung
Cyclo(L-Leu-L-Pro) is a diketopiperazine metabolite that has been isolated from various bacterial and fungal species including Streptomyces. It is active against twelve strains of vancomycin-resistant enterococci (VRE) with MIC values of 12.5 μg/ml for E. faecalis strains K-99-34, K-00-184, and K-00-221. It also inhibits growth of K562, HL-60, and U937 leukemia cells in a concentration-dependent manner when used at concentrations of 1-500 μg/ml. Cyclo(L-Leu-L-Pro) also has antifouling activity, inhibiting attachment of B. amphitrite larva with an EC50 value of 0.15 mM.
Verwenden
Sorbicillin analog. A bioactive secondary metabolites from terrestrial Streptomyces species TN262.