Atpenin A 5
Grundinformationen
- CAS
119509-24-9- Standard-SMILES
COc1[nH]c(=O)c(C(=O)[C@@H](C)C[C@H](C)[C@@H](Cl)CCl)c(O)c1OC- InChIKey
OVULNOOPECCZRG-CIUDSAMLSA-N- Summenformel
- C15H21Cl2NO5
- Durchschnittliche Molmasse
- 366,2 g/mol
- Monoisotopische Masse
- 365,0796782
Überblick
from Penicillium sp. FO-125; MW C15-H21-N-O5-Cl2
Namen und Bezeichner
- Bevorzugter Name
- Atpenin A 5
- IUPAC
- 3-[(2S,4S,5R)-5,6-dichloro-2,4-dimethylhexanoyl]-4-hydroxy-5,6-dimethoxy-1H-pyridin-2-one
- Englischer Name
- atpenin A5
- Summenformel
- C15H21Cl2NO5
- Molmasse
- 366.24
Namen und Synonyme
Atpenin A5119509-24-93-[(2S,4S,5R)-5,6-DICHLORO-2,4-DIMETHYL-1-OXOHEXYL]-4-HYDROXY-5,6-DIMETHOXY-2(1H)-PYRIDINONEDTXSID601524783-[(2S,4S,5R)-5,6-dichloro-2,4-dimethylhexanoyl]-4-hydroxy-5,6-dimethoxy-1H-pyridin-2-one3-[(2S,4S,5R)-5,6-dichloro-2,4-dimethylhexanoyl]-4-hydroxy-5,6-dimethoxy-1,2-dihydropyridin-2-oneAtpenin A 53-((2S,4S,5R)-5,6-dichloro-2,4-dimethyl-1-oxohexyl)-4-hydroxy-5,6-dimethoxy-2(1H)-pyridinone3-((2S,4S,5R)-5,6-dichloro-2,4-dimethylhexanoyl)-4-hydroxy-5,6-dimethoxy-1,2-dihydropyridin-2-one3-((2S,4S,5R)-5,6-dichloro-2,4-dimethylhexanoyl)-4-hydroxy-5,6-dimethoxy-1H-pyridin-2-oneRefChem:560327DTXCID1074969
Weitere Namen anzeigen
FO 125A5Antibiotic FO 125A5Atpenin A5 (Synthetic)Atpenin A5, ubiquinone-binding site mitochondrial complex II inhibitor(2S,4S,5R)-5,6-Dichloro-1-(2,4-dihydroxy-5,6-dimethoxypyridin-3-yl)-2,4-dimethyl-1-hexanone(2S,4S,5R)-1-(2,4-Dihydroxy-5,6-dimethoxy-3-pyridinyl)-2,4-dimethyl-5,6-dichloro-1-hexanonepreconditioning,sensitive,mKATP,Atpenin A 5,Atpenin A5,ischemia,potassium,complex II,Inhibitor,cardioprotective,channel,mitochondrial,Potassium Channel,KcsA,ATP,inhibit,reperfusion,Atpenin A-5
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,8
- Polarare Oberfläche (TPSA)
- 84,9 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 23
- Formalladung
- 0
- Komplexität
- 544
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Physikochemische Eigenschaften
- Schmelzpunkt
- 83 · 83-85℃
- Siedepunkt
- 538.3 · 538.3±50.0 °C(Predicted)
- Dichte
- 1.31 · 1.31±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer, Under inert atmosphere
- Löslichkeit
- Chlroform (Slightly), Ethanol (Slightly), Methanol (Slightly, Sonicated)
- pka
- 4.5 · 4.50±1.00(Predicted)
- Aggregatzustand
- White to off-white powder.
- Farbe
- White to Off-White
Chemie und Industrie
Anwendungen
BeschreibungEnantioselective total synthesis of atpenin A5, a potent mitochondrial complex II (succinate-ubiquinone oxidoreductase) inhibitor, has been achieved by a convergent approach through a coupling reaction between 5-iodo-2,3,4,6-tetraalkoxypyridine and a side-chain aldehyde. The two key segments were synthesized through ortho-metalation/boronation with (MeO)3B/oxidation with mCPBA, ortho-iodination, halogen dance reaction, Sharpless epoxidation and regioselective epoxide-opening reaction.
Ergänzende Hinweise
DefinitionAtpenin A5 belongs to a class of antifungal antibiotics isolated from Penicillium sp. The atpenins are effective against filamentous fungi, particularly Trichophyton sp., and are specific and potent inhibitors of the succinate-ubiquinone reducatase activity of the mitochondrial complex II. Atpenin A5 is the most effective inhibitor against complex II from all the atpenins and has been shown to protect against cardiac-reperfusion injury in rat studies through the stimulation of mitochondrial KATP channels. Atpenin A5 is an inhibitor of SDHB, SDHC and SDHD.
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