| Identification | Back Directory | [Name]
2-Piperidinone, 1-[(2E)-3-[4-(acetyloxy)-3-methoxyphenyl]-1-oxo-2-propen-1-yl]-3-[(3,4,5-trimethoxyphenyl)methylene]-, (3E)- | [CAS]
2293951-00-3 | [Synonyms]
Anti-inflammatory agent 35
2Methoxy4{(E)3oxo3[(E)2oxo3(3,4,5trimethoxybenzylidene)piperidin1yl]prop1en1yl}phenylacetate
2-Methoxy-4-{(E)-3-oxo-3-[(E)-2-oxo-3-(3,4,5- trimethoxybenzylidene)piperidin-1-yl]prop-1-en-1-yl}phenyl acetate
2-Piperidinone, 1-[(2E)-3-[4-(acetyloxy)-3-methoxyphenyl]-1-oxo-2-propen-1-yl]-3-[(3,4,5-trimethoxyphenyl)methylene]-, (3E)- | [Molecular Formula]
C27H29NO8 | [MOL File]
2293951-00-3.mol | [Molecular Weight]
495.52 |
| Chemical Properties | Back Directory | [Boiling point ]
637.5±55.0 °C(Predicted) | [density ]
1.252±0.06 g/cm3(Predicted) | [form ]
Solid | [pka]
-2.04±0.20(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Uses]
Anti-inflammatory agent 35 (compound 5a27) is an orally active curcumin analogue with anti-inflammatory activity. Anti-inflammatory agent 35 blocks mitogen-activated protein kinase (MAPK) signaling and p65 nuclear translocation of NF-kB. Anti-inflammatory agent 35 also inhibits yellow neutrophil infiltration and pro-inflammatory cytokine production. Anti-inflammatory agent 35 significantly attenuates lipopolysaccharide (LPS)-induced acute lung injury (ALI) in vivo[1]. | [in vivo]
Anti-inflammatory agent 35 (compound 5a27) (50 mg/kg; po; single dose, monitored 0-25 min) has a better bioavailability than curcumin (HY-N0005)[1].
Anti-inflammatory agent 35 (10 mg/kg; ip; once daily for 1 week) improves LPS-induced ALI by inhibiting inflammation in mice model[1].
The pharmacokinetic parameters in rats[1]
| Route | Dose (mg/kg) | AUC(0-t) (μg/L·h) | AUC(0-∞) (μg/L·h) | MRT(0-t) (h) | MRT(0-∞) (h) | t1/2 (h) | Tmax (h) | CLz/F (L/h/kg) | Vz/F (L/kg) | Cmax | | p.o | 50 | 231.2 | 325.6 | 7.8 | 12.3 | 6.7 | 3.3 | 5062.6 | 827.1 | 113.3 | | i.v | 5 | 34.3 | 122.4 | 11.3 | 19.9 | 0.2 | 0.1 | 404.4 | 59.5 | 16.4 |
| Animal Model: | ALI mouse model (C57BL/6 mice)[1] | | Dosage: | 10 mg/kg | | Administration: | Intraperitoneal injection, once daily for 1 week; 30 min later every dose, followed by 5 mg/kg LPS, intratracheal injection | | Result: | Significantly normalized the wet/dry ratio of lungs. |
| [IC 50]
p38 MAPK; ERK; I-kappaBalpha; IL-6; p65; NF-κB | [References]
[1] Qian J, et al. Design and synthesis novel di-carbonyl analogs of curcumin (DACs) act as potent anti-inflammatory agents against LPS-induced acute lung injury (ALI). Eur J Med Chem. 2019 Apr 1;167:414-425. DOI:10.1016/j.ejmech.2019.02.042 |
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